High Waist & Pleats
Here’s another great example of how higher waisted trousers can give you nice proportions between your torso and legs, and how pleats can visually break up the expanse of fabric that sits on your hips and thighs. Ignore fashion writers who say that pleats should always be avoided, or that they’re only meant for heavier set men. There’s nothing wrong with pleats if the tailoring is done well, and you can find many good examples in Old Hollywood pictures from the 1930s through ’50s. Slim the legs down a touch, if that’s to your taste. 
That polo shirt, incidentally, was made by Ascot Chang and is currently being sold through The Armoury (where the model above, Nick, works). You could wear it underneath a sport coat for a more casual look. The collar and cuffs will give you the look of a dress shirt, while the half-placket and pique cotton will prevent you from looking like you just came from the office. 
(via philosophyofthewellfed)

High Waist & Pleats

Here’s another great example of how higher waisted trousers can give you nice proportions between your torso and legs, and how pleats can visually break up the expanse of fabric that sits on your hips and thighs. Ignore fashion writers who say that pleats should always be avoided, or that they’re only meant for heavier set men. There’s nothing wrong with pleats if the tailoring is done well, and you can find many good examples in Old Hollywood pictures from the 1930s through ’50s. Slim the legs down a touch, if that’s to your taste. 

That polo shirt, incidentally, was made by Ascot Chang and is currently being sold through The Armoury (where the model above, Nick, works). You could wear it underneath a sport coat for a more casual look. The collar and cuffs will give you the look of a dress shirt, while the half-placket and pique cotton will prevent you from looking like you just came from the office. 

(via philosophyofthewellfed)

The Popover Shirt
Summer is a great time for slightly more casual takes on tailored clothing, and there’s no easier way to dress down a tailored jacket than by using a slightly more casual shirt. So instead of the finely woven cotton dress shirts you might use for the office, consider something in a linen or linen blend. Bolder patterns can also make a shirt look more casual, although you want to be wary of anything that looks too busy. I find blue and white Bengal stripes to be the most useful.
I’ve also come to really like popovers, which is a pullover style with a half placket front. Before sport shirts were made with coat fronts – where the opening went from the collar down to the hem, like a coat – they were made with half-plackets such as this button-down. Nowadays, popovers can be seen a sort of “in-between.” They’re more relaxed than a traditional shirt, but dressier than a polo, which makes them great for those days you want to look sharp, but casual.
The problem with popovers is that they can be sometimes hard to fit. Unlike long-sleeved polos or rugbys – which are styled similarly – these are constructed from a woven, rather than knitted, material. Which means they’re less stretchy. So, in order to easily slide in and out of these things, you want your shirt to be cut a little bigger, but not so big that it looks baggy when worn. 
I ended up going through my shirtmaker Ascot Chang in order to get the right fit, but you could also try many of the ready-to-wear options and be more exacting with your alterations tailor. Try Sid Mashburn, Gitman Brothers, J. Crew, G. Inglese, Individualized Shirts, Fun Time Shirt Company, and Ralph Lauren to start. For something custom, check out Mercer & Sons, Luxire, and our advertiser Proper Cloth. The first will do made-to-order, where you can customize your shirt from a wide range of pre-selected options, while the last two can do made-to-measure, where you’ll get a shirt made according to the body measurements you submit online.  

The Popover Shirt

Summer is a great time for slightly more casual takes on tailored clothing, and there’s no easier way to dress down a tailored jacket than by using a slightly more casual shirt. So instead of the finely woven cotton dress shirts you might use for the office, consider something in a linen or linen blend. Bolder patterns can also make a shirt look more casual, although you want to be wary of anything that looks too busy. I find blue and white Bengal stripes to be the most useful.

I’ve also come to really like popovers, which is a pullover style with a half placket front. Before sport shirts were made with coat fronts – where the opening went from the collar down to the hem, like a coat – they were made with half-plackets such as this button-down. Nowadays, popovers can be seen a sort of “in-between.” They’re more relaxed than a traditional shirt, but dressier than a polo, which makes them great for those days you want to look sharp, but casual.

The problem with popovers is that they can be sometimes hard to fit. Unlike long-sleeved polos or rugbys – which are styled similarly – these are constructed from a woven, rather than knitted, material. Which means they’re less stretchy. So, in order to easily slide in and out of these things, you want your shirt to be cut a little bigger, but not so big that it looks baggy when worn. 

I ended up going through my shirtmaker Ascot Chang in order to get the right fit, but you could also try many of the ready-to-wear options and be more exacting with your alterations tailor. Try Sid Mashburn, Gitman Brothers, J. Crew, G. Inglese, Individualized Shirts, Fun Time Shirt Company, and Ralph Lauren to start. For something custom, check out Mercer & Sons, Luxire, and our advertiser Proper Cloth. The first will do made-to-order, where you can customize your shirt from a wide range of pre-selected options, while the last two can do made-to-measure, where you’ll get a shirt made according to the body measurements you submit online.  

The Very Versatile Casual Suit
I love suits, but being that I don’t work in law or finance, don’t live on the East Coast, and am (what I’d like to think) a relatively young guy in his mid-30s, I don’t get to wear them very often. So, I buy most of mine these days in causal materials, such as cotton, linen, and corduroy. That way, I can have a casual suit for social occasions, or break the pieces up and wear them separately. In the above, for example, the brown sport coat is actually a suit jacket that’s part of a cigar linen suit I bought last year.
With a casual suit, even the trousers can be worn separately. Corduroy, linen, and cotton suit trousers just become … well, corduroy pants, linen pants, and chinos. And since these pieces came as part of a suit, the jacket’s length will be a bit longer than most sport coats these days (which often look too short anyway) and the pants will have a slightly higher rise (which I think looks more flattering anyhow).
The only downside, of course, is the cost. A good suit – whether made from a fine worsted wool or a more casual material – can run you $1,000 or more at the retail level. Depending on how you break up that price, that’s a lot more than what you’d typically pay for a casual pair of pants and a sport coat. Those won’t match up to form a suit when you need them to, but they will be less expensive.
If you can afford them, however, casual suits can be great, and they’ll give you a lot of versatility in your wardrobe. You can find them at most places that sell tailored clothing (try our suit buying guides here and here). No Man Walks Alone also has a rare Minnis Fresco option this summer. Fresco is an open-weave, worsted wool (which makes it breathable on hot days) and it has a bit of a texture (which means you can wear the jacket as a sport coat). Remember: the rule of thumb for wearing suit jackets as sport coats is to avoid anything that’s made from a very silky or finely woven wool. It should never look like you’re wearing a suit jacket by itself, even if you are.
Pictured above: tan linen pants from Hickey Freeman; cigar linen suit jacket by Napolisumisura (made from W. Bill linen); light blue shirt by Ascot Chang (made from Simonnot Godard chambray); dark brown loafers from Edward Green; dark brown belt from Brooks Brothers; and white cotton pocket square from Simonnot Godard

The Very Versatile Casual Suit

I love suits, but being that I don’t work in law or finance, don’t live on the East Coast, and am (what I’d like to think) a relatively young guy in his mid-30s, I don’t get to wear them very often. So, I buy most of mine these days in causal materials, such as cotton, linen, and corduroy. That way, I can have a casual suit for social occasions, or break the pieces up and wear them separately. In the above, for example, the brown sport coat is actually a suit jacket that’s part of a cigar linen suit I bought last year.

With a casual suit, even the trousers can be worn separately. Corduroy, linen, and cotton suit trousers just become … well, corduroy pants, linen pants, and chinos. And since these pieces came as part of a suit, the jacket’s length will be a bit longer than most sport coats these days (which often look too short anyway) and the pants will have a slightly higher rise (which I think looks more flattering anyhow).

The only downside, of course, is the cost. A good suit – whether made from a fine worsted wool or a more casual material – can run you $1,000 or more at the retail level. Depending on how you break up that price, that’s a lot more than what you’d typically pay for a casual pair of pants and a sport coat. Those won’t match up to form a suit when you need them to, but they will be less expensive.

If you can afford them, however, casual suits can be great, and they’ll give you a lot of versatility in your wardrobe. You can find them at most places that sell tailored clothing (try our suit buying guides here and here). No Man Walks Alone also has a rare Minnis Fresco option this summer. Fresco is an open-weave, worsted wool (which makes it breathable on hot days) and it has a bit of a texture (which means you can wear the jacket as a sport coat). Remember: the rule of thumb for wearing suit jackets as sport coats is to avoid anything that’s made from a very silky or finely woven wool. It should never look like you’re wearing a suit jacket by itself, even if you are.

Pictured above: tan linen pants from Hickey Freeman; cigar linen suit jacket by Napolisumisura (made from W. Bill linen); light blue shirt by Ascot Chang (made from Simonnot Godard chambray); dark brown loafers from Edward Green; dark brown belt from Brooks Brothers; and white cotton pocket square from Simonnot Godard

Real People: Dressing Down a Suit

Open any men’s fashion magazine nowadays and you can read about the 101 ways to dress down a suit. The problem is, the suit is more often than not a sober looking garment, so when you try to “dress it down,” it can be like painting a mustache on the Mona Lisa. A safer way to dress down a suit is to simply get a more casual suit. Instead of one made from a smooth, worsted wool, try something in cotton, linen, corduroy, or even tweed. That way, your suit is inherently more casual, and you won’t have to awkwardly try to pull back its formality with some unusual accessory.

That does require buying a separate suit for casual occasions, however, which can get expensive (especially once you factor in seasonal fabrics). If you want to try to dress down a standard business suit, try pairing one with a softly colored pastel shirt, perhaps something in pink, lavender, or sea green. Any of those will be more casual than your standard solid whites or light blues, and can help both soften the edge of a suit while also enlivening its look. If need be, you can dress it down further with some casual footwear, such as tassel loafers or something made from suede. Our friend Niyi in New York City shows how well can look above.

You can get pastel colored shirts at any number of places these days. Ralph Lauren and Brooks Brothers are good starts, so long as you stay away from the ones with embroidered logos. Our advertiser Ledbury has a lime green one in their “short run shirts” section until the end of today. If you want something custom made, I can recommend Ascot Chang. They have offices in New York City and Los Angeles, although they also tour throughout the United States to meet clients (I meet them in San Francisco twice a year). They do great work, but being bespoke, they are a bit pricey. For something more affordable, but custom, there’s Cottonwork and our advertiser Proper Cloth. For something affordable, but ready to wear, there’s TM Lewin and Thin Red Line.

An Affordable Spring Look
Outerwear tends to be expensive, but it doesn’t have to be. Depending on your budget, you can get relatively affordable coats and jackets nowadays from Club Monaco, J. Crew, Brooks Brothers, and Ralph Lauren. At the end of every season, they’ll have nice looking designs for about $150-200 (Brooks Brothers and Ralph Lauren have really good mid-season sales as well). More affordably, there’s Pointer’s chore coat for $87. It looks pretty good if you like workwear.   
For rainy days, I sometimes wear LL Bean’s Trail Model Rain Jacket with jeans, a Shetland sweater, and some LL Bean boots. The shell is made from a waterproof rip stop nylon and the interior seams are taped. The pocket bags are also made of mesh, so that if you store away any wet things, they’ll dry quicker. The best part? It’s $79. Possibly $71 if you wait for one of LL Bean’s occasional 10% off coupons. Additionally, they have a similar jacket this season under their “Signature” line. Although I haven’t handled it, the jacket looks like it comes without a chest logo (which the mainline does, unfortunately, although it’s tonal). I also assume it fits slimmer all around.
In the photo above, I’ve paired my LL Bean rain jacket with an oxford cloth button down shirt from Ascot Chang, a Shetland sweater from O’Connell’s, and a pair of straight legged jeans from 3sixteen. All of these tend to be a bit on the pricey side, but you can find more affordable alternatives at a number of places. Brooks Brothers will have oxford cloth button downs for about $50 during sale season, while Kamakura sells them for about $79 year round. More affordable Shetlands can be had for about $75-100 at Brooks Brothers and LL Bean when they’re on discount (although they don’t always carry them). Lastly, raw selvedge denim jeans can be had for about $89 from our advertiser Gustin, or $82 from Unbranded. Both get regularly recommended in the denim community.
Together, these pieces make for a reasonably classic look, and more importantly, can be had for not too much money. 

An Affordable Spring Look

Outerwear tends to be expensive, but it doesn’t have to be. Depending on your budget, you can get relatively affordable coats and jackets nowadays from Club Monaco, J. Crew, Brooks Brothers, and Ralph Lauren. At the end of every season, they’ll have nice looking designs for about $150-200 (Brooks Brothers and Ralph Lauren have really good mid-season sales as well). More affordably, there’s Pointer’s chore coat for $87. It looks pretty good if you like workwear.   

For rainy days, I sometimes wear LL Bean’s Trail Model Rain Jacket with jeans, a Shetland sweater, and some LL Bean boots. The shell is made from a waterproof rip stop nylon and the interior seams are taped. The pocket bags are also made of mesh, so that if you store away any wet things, they’ll dry quicker. The best part? It’s $79. Possibly $71 if you wait for one of LL Bean’s occasional 10% off coupons. Additionally, they have a similar jacket this season under their “Signature” line. Although I haven’t handled it, the jacket looks like it comes without a chest logo (which the mainline does, unfortunately, although it’s tonal). I also assume it fits slimmer all around.

In the photo above, I’ve paired my LL Bean rain jacket with an oxford cloth button down shirt from Ascot Chang, a Shetland sweater from O’Connell’s, and a pair of straight legged jeans from 3sixteen. All of these tend to be a bit on the pricey side, but you can find more affordable alternatives at a number of places. Brooks Brothers will have oxford cloth button downs for about $50 during sale season, while Kamakura sells them for about $79 year round. More affordable Shetlands can be had for about $75-100 at Brooks Brothers and LL Bean when they’re on discount (although they don’t always carry them). Lastly, raw selvedge denim jeans can be had for about $89 from our advertiser Gustin, or $82 from Unbranded. Both get regularly recommended in the denim community.

Together, these pieces make for a reasonably classic look, and more importantly, can be had for not too much money. 

Tartan Shirts for Fall
These old tartan shirts by Brooks Brothers are great examples of the kind of fall shirts that pair well with tweed jackets and corduroy sport coats. They have an autumnal sensibility where a smooth, light blue shirt might be lacking, and their bold patterns can help dress down the look of a tailored jacket. 
When you first delve into the world of tartans, you may come across some unfamiliar terminology that, at first glance, can be a bit misleading. For example, “ancient” and “modern” don’t refer to the age of a pattern. Instead, “modern” just means the pattern was made in its “standard” colors, while “ancient” refers to something made in lighter tones (e.g. this Lindsay tartan in both modern and ancient variations). As you can see, the idea for “ancient” is to create something with an aged or weathered look, not too unlike how denim producers sometimes create pre-distressed jeans. For tartans, that means making the blues and greens a bit more muted, and scaling back the intensity of the yellows and reds. The effect is a plaid that looks like it has been worn for years. 
It’s also common to see tartans described as either “hunting” or “dress,” but again, these don’t mean what you think they mean. Instead, hunting tartans are simply tartans that are based more in greens and blues, while dress tartans make more use of white. Despite the name, dress tartans are just as casual as hunting variations. See, for example, Hunting Stewart versus Dress Stewart.
This is all just background, of course. The most important thing is to find a pattern that you like. The first one you see above, set at the front, is blackwatch shirt, and can be bought this season through O’Connell’s, J. Press, and our advertiser Ledbury. The one behind that looks to be either a MacKenzie or Hunting Stewart, and can be had through Ralph Lauren in modern and ancient variations. The dress tartan furthest back is a bit harder to find, but you get similar designs through Gant (in two varieties), Ralph Lauren, and Brooks Brothers. Lastly, readers who have custom shirts made might want to enquire with their tailors. They should have lots of tartan fabrics to choose from, but if not, you can acquire some through Acorn. I’m having this Hunting Stewart made up for me now through Ascot Chang, and plan to wear it this fall with brown corduroys and suede shoes.  
(Photo via Glengarry Sporting Club)

Tartan Shirts for Fall

These old tartan shirts by Brooks Brothers are great examples of the kind of fall shirts that pair well with tweed jackets and corduroy sport coats. They have an autumnal sensibility where a smooth, light blue shirt might be lacking, and their bold patterns can help dress down the look of a tailored jacket. 

When you first delve into the world of tartans, you may come across some unfamiliar terminology that, at first glance, can be a bit misleading. For example, “ancient” and “modern” don’t refer to the age of a pattern. Instead, “modern” just means the pattern was made in its “standard” colors, while “ancient” refers to something made in lighter tones (e.g. this Lindsay tartan in both modern and ancient variations). As you can see, the idea for “ancient” is to create something with an aged or weathered look, not too unlike how denim producers sometimes create pre-distressed jeans. For tartans, that means making the blues and greens a bit more muted, and scaling back the intensity of the yellows and reds. The effect is a plaid that looks like it has been worn for years. 

It’s also common to see tartans described as either “hunting” or “dress,” but again, these don’t mean what you think they mean. Instead, hunting tartans are simply tartans that are based more in greens and blues, while dress tartans make more use of white. Despite the name, dress tartans are just as casual as hunting variations. See, for example, Hunting Stewart versus Dress Stewart.

This is all just background, of course. The most important thing is to find a pattern that you like. The first one you see above, set at the front, is blackwatch shirt, and can be bought this season through O’Connell’s, J. Press, and our advertiser Ledbury. The one behind that looks to be either a MacKenzie or Hunting Stewart, and can be had through Ralph Lauren in modern and ancient variations. The dress tartan furthest back is a bit harder to find, but you get similar designs through Gant (in two varieties), Ralph Lauren, and Brooks Brothers. Lastly, readers who have custom shirts made might want to enquire with their tailors. They should have lots of tartan fabrics to choose from, but if not, you can acquire some through Acorn. I’m having this Hunting Stewart made up for me now through Ascot Chang, and plan to wear it this fall with brown corduroys and suede shoes.  

(Photo via Glengarry Sporting Club)

The Basic Shirt Wardrobe
I recently accepted that my shirts don’t fit me anymore. Every time I sit down, the placket gapes, which either means my shirts have magically shrunken just at the midsection, or that I’ve gotten fatter. Whatever the reason, I’ve asked my shirtmaker, Ascot Chang, to make me a new set of shirts, which means I’ve had to decide what’s the bare minimum I need, based on what I wore most often before. Of course, what’s basic and essential for you might be totally different, but I thought I’d share my list, in case some readers find it helpful.
Three blue oxford cloth button downs (aka OCBDs): I realize that not everyone likes OCBDs and they can be too American for some. However, I’m unapologetic in my love for them and find they go really well with a range of casual ensembles – from being worn underneath sport coats or sweaters, or just alone with a pair of chinos, corduroys, or wool trousers. If your tastes run even more American than mine, you can add another OCBD in a solid pink or light blue Bengal stripe. White OCBDs can also look pretty good with a pair of jeans. 
Two solid white shirts: These can be worn during the evenings, with suits, or just when you’re feeling fancy. I’ve found that light blue is much more wearable than white, but it’s good to have a couple of these on hand. I recommend getting them in either a basic poplin or twill fabric. You can also get them with French cuffs, if you’d like.
Five solid light blue shirts: It’s almost impossible to go wrong with a solid light blue shirt. The color complements any complexion and can be successfully paired with almost any suit, sport coat, or tie (the exception is maybe a light blue jacket, but who owns those?). You can get these in a plain poplin weave, but I find end-on-end and a dressy chambray to be much more interesting. They have a crisscrossing of blue and white yarns that make them look more appealing, but aren’t so busy that they force the shirt into casualwear. 
Two shirts in a mix of pin and dress stripes (either one of each or two of one): Striped shirts are really useful if most of your tailored jackets are in solid colors. They help add a bit of visual interest and keep your patterned tie from looking too lonely. For what it’s worth, I find the wider-spaced dress stripes to be easier to wear than more densely striped ones, and light blue to be easier to wear than dark blue (reason being that it’s easier to wear things with tonal variation, so dark jackets go well with light blue shirts and dark- or medium-toned ties, rather than a mix of darks in all three). Darker blue dress stripes can be nice, however, if you want a bit more variation in your wardrobe and don’t wear ties often. Brown pinstripes are also a good choice. 
Three shirts in a mix of Bengal and candy stripes: Same logic as the pin and dress stripes, but just in a bolder pattern. Mix your pin and dress stripes with boldly patterned ties, and your Bengal and candy stripes with subtle ones. By varying the scale of the two patterns, you ensure that your shirt and tie will never compete for attention. Light blues are again great, but if you want darker blues, I find they’re easier to wear here, for some reason, than in pin or dress stripes. 
Four casual weekend shirts: Finally, some casual shirts for the weekend. Depending on how hot or cold your climate gets, I recommend getting these in seasonal fabrics. For spring/ summer, you can go with madras, linen, or voile. Those will be very airy and breathable, making them nice for hot, humid days. For fall/ winter, you can swap these out for brushed cottons, wool/ cotton blends, and heavy twills. I find that graph checks and tattersalls also look good underneath tweed sport coats, and can be worn alone with a pair of corduroy trousers and a sweater.
This gives you a total of nineteen shirts for each season. Fifteen for the workweek, and four for the weekend. That should be enough to get you through two weeks before laundry day, with enough extra so that you’re not in danger of being shirtless if you go a few days past or stain something during a particularly good meal.
And that’s my version of a basic shirt wardrobe.

The Basic Shirt Wardrobe

I recently accepted that my shirts don’t fit me anymore. Every time I sit down, the placket gapes, which either means my shirts have magically shrunken just at the midsection, or that I’ve gotten fatter. Whatever the reason, I’ve asked my shirtmaker, Ascot Chang, to make me a new set of shirts, which means I’ve had to decide what’s the bare minimum I need, based on what I wore most often before. Of course, what’s basic and essential for you might be totally different, but I thought I’d share my list, in case some readers find it helpful.

Three blue oxford cloth button downs (aka OCBDs): I realize that not everyone likes OCBDs and they can be too American for some. However, I’m unapologetic in my love for them and find they go really well with a range of casual ensembles – from being worn underneath sport coats or sweaters, or just alone with a pair of chinos, corduroys, or wool trousers. If your tastes run even more American than mine, you can add another OCBD in a solid pink or light blue Bengal stripe. White OCBDs can also look pretty good with a pair of jeans. 

Two solid white shirts: These can be worn during the evenings, with suits, or just when you’re feeling fancy. I’ve found that light blue is much more wearable than white, but it’s good to have a couple of these on hand. I recommend getting them in either a basic poplin or twill fabric. You can also get them with French cuffs, if you’d like.

Five solid light blue shirts: It’s almost impossible to go wrong with a solid light blue shirt. The color complements any complexion and can be successfully paired with almost any suit, sport coat, or tie (the exception is maybe a light blue jacket, but who owns those?). You can get these in a plain poplin weave, but I find end-on-end and a dressy chambray to be much more interesting. They have a crisscrossing of blue and white yarns that make them look more appealing, but aren’t so busy that they force the shirt into casualwear. 

Two shirts in a mix of pin and dress stripes (either one of each or two of one): Striped shirts are really useful if most of your tailored jackets are in solid colors. They help add a bit of visual interest and keep your patterned tie from looking too lonely. For what it’s worth, I find the wider-spaced dress stripes to be easier to wear than more densely striped ones, and light blue to be easier to wear than dark blue (reason being that it’s easier to wear things with tonal variation, so dark jackets go well with light blue shirts and dark- or medium-toned ties, rather than a mix of darks in all three). Darker blue dress stripes can be nice, however, if you want a bit more variation in your wardrobe and don’t wear ties often. Brown pinstripes are also a good choice. 

Three shirts in a mix of Bengal and candy stripes: Same logic as the pin and dress stripes, but just in a bolder pattern. Mix your pin and dress stripes with boldly patterned ties, and your Bengal and candy stripes with subtle ones. By varying the scale of the two patterns, you ensure that your shirt and tie will never compete for attention. Light blues are again great, but if you want darker blues, I find they’re easier to wear here, for some reason, than in pin or dress stripes. 

Four casual weekend shirts: Finally, some casual shirts for the weekend. Depending on how hot or cold your climate gets, I recommend getting these in seasonal fabrics. For spring/ summer, you can go with madras, linen, or voile. Those will be very airy and breathable, making them nice for hot, humid days. For fall/ winter, you can swap these out for brushed cottons, wool/ cotton blends, and heavy twills. I find that graph checks and tattersalls also look good underneath tweed sport coats, and can be worn alone with a pair of corduroy trousers and a sweater.

This gives you a total of nineteen shirts for each season. Fifteen for the workweek, and four for the weekend. That should be enough to get you through two weeks before laundry day, with enough extra so that you’re not in danger of being shirtless if you go a few days past or stain something during a particularly good meal.

And that’s my version of a basic shirt wardrobe.

A Popover for Summer
The spate of hot weather recently had me thinking about what kind of shirts I might like to get this summer. High on the list are popovers. A popover is a woven shirt with a placket that only goes partially down the chest. I suspect they’re a holdover from when sport shirts weren’t all made with coat fronts (an early version of such a design can be seen here). They’re less common now, but I think they can look quite good on men with slim stomachs. They’re more relaxed than a traditional shirt, but more dressed up than a polo shirt, and this in-between-ness makes them just right for when you want to look smart on casual days.
I bought this one from Gant two years ago, but sadly the cut didn’t work out for me, so now I’m on the market for another. The nicest one I’ve seen is by Isaia, which is pictured above. My friend Agyesh, who actually took the image shown, works for Isaia and tells me that the brand still makes these. They should be available at Saks Fifth Avenue (especially the one in New York City), but if not, any store that offers Isaia’s made-to-measure program will be able to custom make one for you. You can get the model above, or one with a button-down collar and mitered placket. 
In addition, Sid Mashburn has some very handsome ones with a deep, long placket. Epaulet, New England Shirt Company, and Wharf also look promising. 
For something a bit more fashion forward, there’s a small selection at Need Supply, and a few designs by Engineered Garments this season at French Garment Cleaners and Oi Polloi. Steven Alan happens to have one of them on sale, which you can knock another 15% off by signing up for their newsletter. For something a bit more workwear-ish, check out Thoroughstitch and Levis Vintage Clothing.
All the aforementioned companies make really nice shirts, but they can be a bit expensive. If you want something more affordable, and don’t mind short-sleeves, J Crew has a bunch on sale right now. You can take 30% off the listed price by punching in the code SUMMER at checkout.
And finally, for people who need a special size, there are a number of options for custom. In addition to the Isaia you see above, Individualized Shirts and Mercer & Sons have made-to-order programs. They’re not exactly made-to-measure, meaning you can’t get things made to your exact measurements, but you can choose from different cuts and patterns to get the shirt you need (for Individualized, you’ll have to go to their factory, however). Luxire also makes them through an online made-to-measure service, and I can recommend my shirtmaker Ascot Chang for bespoke. Ascot Chang is actually running a promotion right now where you can get one shirt free for every six you order. Granted, they’re not cheap – so buying six at a time is pretty expensive – but they do fantastic work and offer tremendous value at their price point. You can visit them at one of their stores, or catch them on their US tour this month. 
(Photo credit: Mad House, Inc)

A Popover for Summer

The spate of hot weather recently had me thinking about what kind of shirts I might like to get this summer. High on the list are popovers. A popover is a woven shirt with a placket that only goes partially down the chest. I suspect they’re a holdover from when sport shirts weren’t all made with coat fronts (an early version of such a design can be seen here). They’re less common now, but I think they can look quite good on men with slim stomachs. They’re more relaxed than a traditional shirt, but more dressed up than a polo shirt, and this in-between-ness makes them just right for when you want to look smart on casual days.

I bought this one from Gant two years ago, but sadly the cut didn’t work out for me, so now I’m on the market for another. The nicest one I’ve seen is by Isaia, which is pictured above. My friend Agyesh, who actually took the image shown, works for Isaia and tells me that the brand still makes these. They should be available at Saks Fifth Avenue (especially the one in New York City), but if not, any store that offers Isaia’s made-to-measure program will be able to custom make one for you. You can get the model above, or one with a button-down collar and mitered placket. 

In addition, Sid Mashburn has some very handsome ones with a deep, long placket. EpauletNew England Shirt Company, and Wharf also look promising. 

For something a bit more fashion forward, there’s a small selection at Need Supply, and a few designs by Engineered Garments this season at French Garment Cleaners and Oi PolloiSteven Alan happens to have one of them on sale, which you can knock another 15% off by signing up for their newsletter. For something a bit more workwear-ish, check out Thoroughstitch and Levis Vintage Clothing.

All the aforementioned companies make really nice shirts, but they can be a bit expensive. If you want something more affordable, and don’t mind short-sleeves, J Crew has a bunch on sale right now. You can take 30% off the listed price by punching in the code SUMMER at checkout.

And finally, for people who need a special size, there are a number of options for custom. In addition to the Isaia you see above, Individualized Shirts and Mercer & Sons have made-to-order programs. They’re not exactly made-to-measure, meaning you can’t get things made to your exact measurements, but you can choose from different cuts and patterns to get the shirt you need (for Individualized, you’ll have to go to their factory, however). Luxire also makes them through an online made-to-measure service, and I can recommend my shirtmaker Ascot Chang for bespoke. Ascot Chang is actually running a promotion right now where you can get one shirt free for every six you order. Granted, they’re not cheap – so buying six at a time is pretty expensive – but they do fantastic work and offer tremendous value at their price point. You can visit them at one of their stores, or catch them on their US tour this month. 

(Photo credit: Mad House, Inc)

A Simple Summer Look
I love this Apparel Arts illustration. I found it last year on an online men’s clothing forum, and put it in my head to try to find similar pieces. Unfortunately, by the time I did, summer had already passed. This year, however, I’ll be wearing this on more than a few occasions once the weather gets hot (though, I’ll probably leave the ascot and pipe to more dashing men).
The great thing about this is how stylish it looks with just a few simple pieces. To get something like this for yourself, consider this long-sleeved polo from Kent Wang. Though not technically the same as what you see above, I think long sleeves rolled up look better than short ones. I also find that long sleeved polos have the advantage of being able to do double duty underneath sport coats. They show the bit of requisite shirt cuff underneath the jacket sleeve, and ensure that no bare wrists will be exposed when you move your arms. If you want something sportier, however, Kent has a number of short sleeve options as well.
The upside to Kent’s polos is that they have a few “button up shirt details” that make them look a bit smarter than your average tennis shirt. The collar band, for example, is reinforced, so the collar doesn’t flop down and lay flat against your shoulder (like you’d see on most polos). The downside, however, is that they fit very slim and the sleeves can be a bit tight. Kent has measurements posted though, and he accepts returns.
For other options, Jesse has recommended Lands’ End. I also really like this new polo at The Armoury, which I believe was made for them by Ascot Chang. To order one, you’ll have to call or email their store (expect the price to be higher than either Kent’s or Lands’ End).
Tan trousers are harder to find. For mine, I bought a pair of flannel ones from Howard Yount, but they’re sold out now and won’t be restocking until fall. Flannel has a bit of richness and mottling that’ll help keep this from looking like a Best Buy employee uniform. You can find something similar at the moment at O’Connell’s and J Press, the second of which is having a sale right now. And though they’re not tan, these Pantas look fantastic. Their prices aren’t cheap, but their pants are some of the highest quality you’ll find in the ready-to-wear market.  
Finally, for the creped-soled shoes, consider some of the options I mentioned a few weeks ago. I think pair of sueded, dark brown chukkas with rubber crepe soles here would look great.

A Simple Summer Look

I love this Apparel Arts illustration. I found it last year on an online men’s clothing forum, and put it in my head to try to find similar pieces. Unfortunately, by the time I did, summer had already passed. This year, however, I’ll be wearing this on more than a few occasions once the weather gets hot (though, I’ll probably leave the ascot and pipe to more dashing men).

The great thing about this is how stylish it looks with just a few simple pieces. To get something like this for yourself, consider this long-sleeved polo from Kent Wang. Though not technically the same as what you see above, I think long sleeves rolled up look better than short ones. I also find that long sleeved polos have the advantage of being able to do double duty underneath sport coats. They show the bit of requisite shirt cuff underneath the jacket sleeve, and ensure that no bare wrists will be exposed when you move your arms. If you want something sportier, however, Kent has a number of short sleeve options as well.

The upside to Kent’s polos is that they have a few “button up shirt details” that make them look a bit smarter than your average tennis shirt. The collar band, for example, is reinforced, so the collar doesn’t flop down and lay flat against your shoulder (like you’d see on most polos). The downside, however, is that they fit very slim and the sleeves can be a bit tight. Kent has measurements posted though, and he accepts returns.

For other options, Jesse has recommended Lands’ End. I also really like this new polo at The Armoury, which I believe was made for them by Ascot Chang. To order one, you’ll have to call or email their store (expect the price to be higher than either Kent’s or Lands’ End).

Tan trousers are harder to find. For mine, I bought a pair of flannel ones from Howard Yount, but they’re sold out now and won’t be restocking until fall. Flannel has a bit of richness and mottling that’ll help keep this from looking like a Best Buy employee uniform. You can find something similar at the moment at O’Connell’s and J Press, the second of which is having a sale right now. And though they’re not tan, these Pantas look fantastic. Their prices aren’t cheap, but their pants are some of the highest quality you’ll find in the ready-to-wear market.  

Finally, for the creped-soled shoes, consider some of the options I mentioned a few weeks ago. I think pair of sueded, dark brown chukkas with rubber crepe soles here would look great.

The OCBD Shirt Series, Part VI: Our Recommendations
After reviewing so many companies, we thought it’d be useful to say which we recommend the most. Obviously much depends on your taste, build, and budget. The great thing about having such a varied market, however, is that there’s almost something for everyone. 
If you want something traditional, I recommend either Mercer & Sons or O’Connell’s. Mercer & Sons has a great oxford cloth that’s a bit more variegated in color and nubby in texture than the standard stuff you’d find at Brooks Brothers or J. Press. They also have a fully sized, unlined collar that gives the kind of wrinkly, carefree roll that enthusiasts find so charming. The only problem is that Mercer & Sons’ shirts fit very, very full, so you if you use them, you may have to turn to their made-to-order service. That’s where you can size the body down two and taper it further by two or four inches. To find out if this might work for you, email Mercer and ask for their shirt measurements.
The other exceptional option is O’Connell’s, who has one of the best button down collars I’ve seen. Ethan there tells me that they’re also working on a new model based on mid-century Brooks Brothers designs. That should be released sometime by the end of this year, and we’ll be certain to announce it when it does.
For something slim fitting, I really like Kamakura. They make two fits – a regular cut and a slim fit. I suspect the slim fit is just the regular cut, but with darts in the back. Admittedly, darts look a bit strange to me on an OCBD, but the body of the shirt still fits fairly well, so long as you have a slim stomach. Either way, both the regular and slim fits have great looking collars. See it worn here at Ivy Style.
You may also want to consider Brooks Brothers’ slim and extra-slim fits once they go on sale. I like Kamakura’s shirts better, but on the downside, they never go on sale. Brooks Brothers’ oxfords, on the other hand, regularly get discounted to about $50 a pop.
Conversely, if money is no object, you can check out Harry Stedman, who makes a pretty nice design from a hodgepodge of classic American details. Just note that they fit pretty slim, so if you’re a regular 36, you may want to opt for a 38 or simply a size small.  
If you want something dressy, try Ledbury. Theirs isn’t a conventional OCBD like the others we’ve covered here. The fabric is a smoother Thomas Mason cloth that’s somewhat reminiscent of Royal Oxford, and the shirt doesn’t have details such as box pleats or chest pockets. All in all, it’s just a dressier looking shirt, which can be good depending on what you’re going for. 
For something affordable, I like Land’s End’s tailored fit oxfords. Their fabric feels better than what Uniqlo and Lands’ End Canvas offers, and the fit isn’t as trendy. Though, depending on your style, Uniqlo and Lands’ End Canvas’ slimmer fits and shorter collars might work better for you. Either way, be sure to wait for sales. Lands’ End oxfords can be had for about $30 or $35, while Uniqlo and Lands’ End Canvas will often be sold for about $20.
Finally, if you want to get something custom made, I can recommend Cottonwork and Ascot Chang from personal experience. Cottonwork, as I’ve noted, does online made to measure, while Ascot Chang does full bespoke. The second tends to have an advantage in terms of executing an ideal fit, but the first will be considerably more affordable. Both do good work, however. You may also want to look into other custom shirtmakers, such as CEGO, Geneva, Anto, Dege & Skinner, and many others. Check StyleForum for recommendations, and perhaps acquaint yourself with the process of buying custom shirts through these posts I wrote last year. 

The OCBD Shirt Series, Part VI: Our Recommendations

After reviewing so many companies, we thought it’d be useful to say which we recommend the most. Obviously much depends on your taste, build, and budget. The great thing about having such a varied market, however, is that there’s almost something for everyone. 

If you want something traditional, I recommend either Mercer & Sons or O’Connell’s. Mercer & Sons has a great oxford cloth that’s a bit more variegated in color and nubby in texture than the standard stuff you’d find at Brooks Brothers or J. Press. They also have a fully sized, unlined collar that gives the kind of wrinkly, carefree roll that enthusiasts find so charming. The only problem is that Mercer & Sons’ shirts fit very, very full, so you if you use them, you may have to turn to their made-to-order service. That’s where you can size the body down two and taper it further by two or four inches. To find out if this might work for you, email Mercer and ask for their shirt measurements.

The other exceptional option is O’Connell’s, who has one of the best button down collars I’ve seen. Ethan there tells me that they’re also working on a new model based on mid-century Brooks Brothers designs. That should be released sometime by the end of this year, and we’ll be certain to announce it when it does.

For something slim fitting, I really like Kamakura. They make two fits – a regular cut and a slim fit. I suspect the slim fit is just the regular cut, but with darts in the back. Admittedly, darts look a bit strange to me on an OCBD, but the body of the shirt still fits fairly well, so long as you have a slim stomach. Either way, both the regular and slim fits have great looking collars. See it worn here at Ivy Style.

You may also want to consider Brooks Brothers’ slim and extra-slim fits once they go on sale. I like Kamakura’s shirts better, but on the downside, they never go on sale. Brooks Brothers’ oxfords, on the other hand, regularly get discounted to about $50 a pop.

Conversely, if money is no object, you can check out Harry Stedman, who makes a pretty nice design from a hodgepodge of classic American details. Just note that they fit pretty slim, so if you’re a regular 36, you may want to opt for a 38 or simply a size small.  

If you want something dressy, try Ledbury. Theirs isn’t a conventional OCBD like the others we’ve covered here. The fabric is a smoother Thomas Mason cloth that’s somewhat reminiscent of Royal Oxford, and the shirt doesn’t have details such as box pleats or chest pockets. All in all, it’s just a dressier looking shirt, which can be good depending on what you’re going for. 

For something affordable, I like Land’s End’s tailored fit oxfords. Their fabric feels better than what Uniqlo and Lands’ End Canvas offers, and the fit isn’t as trendy. Though, depending on your style, Uniqlo and Lands’ End Canvas’ slimmer fits and shorter collars might work better for you. Either way, be sure to wait for sales. Lands’ End oxfords can be had for about $30 or $35, while Uniqlo and Lands’ End Canvas will often be sold for about $20.

Finally, if you want to get something custom made, I can recommend Cottonwork and Ascot Chang from personal experience. Cottonwork, as I’ve noted, does online made to measure, while Ascot Chang does full bespoke. The second tends to have an advantage in terms of executing an ideal fit, but the first will be considerably more affordable. Both do good work, however. You may also want to look into other custom shirtmakers, such as CEGO, Geneva, Anto, Dege & Skinner, and many others. Check StyleForum for recommendations, and perhaps acquaint yourself with the process of buying custom shirts through these posts I wrote last year