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.

On Writing and Dressing Well
For my day job, I teach college courses on economic development. My students are smart, but many come to college not knowing how to write a basic paper. I get paid to teach them about development, not English, but in the course of reading so many students’ essays, I’ve come up with a few ideas on how they can generally improve their writing. I think some of the same lessons can be insightful for those interested in dressing as well.
Let’s start with what’s wrong with their papers. Students often abuse thesauruses and write long, needless sentences, many of which are not arranged in any coherent order. Their papers frequently lack theses, and when there is one, it’s unclear how each part supports their conclusion. 
My general idea is that students can improve if they just write simply and unpretentiously, erring on the side of clarity. Two strategies would be to use shorter sentences and edit things down as tightly as possible. They should also avoid using fancy words to dress up their prose and instead focus on communicating a strong, central idea. Simplicity, clarity, and coherency. Have one meaningful thing to say and say it well. 
The basic principles for dressing are similar. Of course, some men should just pull up their pants and wear jackets that fit. Among men who already put in effort, however, most would fare better by not trying so hard to look “stylish.” Not unlike students who try to force sounding sophisticated, these men should strip away needless details and accoutrements. Tightly edit things down, use simple garments, and express one idea. 
They should also ensure that there’s some coherency and harmony. Wearing avant-garde designer sweaters with traditionally tailored sport coats, for example, doesn’t work. Nor do denim trucker jackets with neckties, frankly. It’s important to keep things in-synch by sticking within the same aesthetic family, seasonal mood, and level of formality. This is the sartorial equivalent of supporting a thesis.
Of course, there are many men who are incredibly stylish and break all sorts of these “rules.” Hirofumi Kurino and Yasuto Kamoshita, both of whom work for United Arrows, are two perfect examples. Dressing is also more of an art than writing about social theories, so there’s more room for creative license. 
However, if you’re a novice, I think you would do better by taking the basic approach to dressing. Rely on simple things, edit things down tightly, and make sure each piece supports another in some harmonious manner. Maybe that’s a madras shirt, khaki linen pants, and brown leather loafers for a causal summer weekend. Or it’s a navy suit, white shirt, black grenadine tie, and black oxford shoes for an evening charity event. Whatever it is, have a thesis and express it clearly and concisely. You can, of course, one day move to more creative forms of expressing yourself, but not before you’ve learned how to write a basic paper. 
* Special thanks to Stephen for helping me edit this article.

On Writing and Dressing Well

For my day job, I teach college courses on economic development. My students are smart, but many come to college not knowing how to write a basic paper. I get paid to teach them about development, not English, but in the course of reading so many students’ essays, I’ve come up with a few ideas on how they can generally improve their writing. I think some of the same lessons can be insightful for those interested in dressing as well.

Let’s start with what’s wrong with their papers. Students often abuse thesauruses and write long, needless sentences, many of which are not arranged in any coherent order. Their papers frequently lack theses, and when there is one, it’s unclear how each part supports their conclusion. 

My general idea is that students can improve if they just write simply and unpretentiously, erring on the side of clarity. Two strategies would be to use shorter sentences and edit things down as tightly as possible. They should also avoid using fancy words to dress up their prose and instead focus on communicating a strong, central idea. Simplicity, clarity, and coherency. Have one meaningful thing to say and say it well. 

The basic principles for dressing are similar. Of course, some men should just pull up their pants and wear jackets that fit. Among men who already put in effort, however, most would fare better by not trying so hard to look “stylish.” Not unlike students who try to force sounding sophisticated, these men should strip away needless details and accoutrements. Tightly edit things down, use simple garments, and express one idea. 

They should also ensure that there’s some coherency and harmony. Wearing avant-garde designer sweaters with traditionally tailored sport coats, for example, doesn’t work. Nor do denim trucker jackets with neckties, frankly. It’s important to keep things in-synch by sticking within the same aesthetic family, seasonal mood, and level of formality. This is the sartorial equivalent of supporting a thesis.

Of course, there are many men who are incredibly stylish and break all sorts of these “rules.” Hirofumi Kurino and Yasuto Kamoshita, both of whom work for United Arrows, are two perfect examples. Dressing is also more of an art than writing about social theories, so there’s more room for creative license. 

However, if you’re a novice, I think you would do better by taking the basic approach to dressing. Rely on simple things, edit things down tightly, and make sure each piece supports another in some harmonious manner. Maybe that’s a madras shirt, khaki linen pants, and brown leather loafers for a causal summer weekend. Or it’s a navy suit, white shirt, black grenadine tie, and black oxford shoes for an evening charity event. Whatever it is, have a thesis and express it clearly and concisely. You can, of course, one day move to more creative forms of expressing yourself, but not before you’ve learned how to write a basic paper. 

* Special thanks to Stephen for helping me edit this article.

Q and Answer
Sam writes:
Having (relatively) recently graduated high school, I have decided that I have crossed the threshold into adulthood, and I would like to dress the part. However, for as long as I can remember, I’ve been wearing graphic t-shirts and the same five or six pairs of jeans which are covered in god-knows-what of irremovable stains.
 During what I want to say was August, a French Connection retailer was having an end of summer sale, so I grabbed a white oxford and some pinstripe slacks which I have fallen in love with and want every excuse to wear.  Now, I am at a point where I don’t know what my next purchase should be. I can’t buy an entire ensemble due to my lack of funds, but I want to make one solid purchase. Something that will be that one bridge from my adolescence pile of clothes to a gentleman’s wardrobe.
First of all, you’re still college aged.  There’s no need to be Alex P. Keaton and wear a suit to class.
I’d focus on upgrading your casual wardrobe.  Don’t wear stained clothes.  Whatever clothes you have that have stains, give them to the goodwill or use them as rags.  Get yourself something plain that fits, even if it’s some t-shirts from Target.  Get yourself a decent pair of blue jeans - Levi’s 514s or 501 shrink-to-fits are a good starting point.  Maybe a pair of slim-fitting J. Crew or Canvas chinos.  Simplify, simplify, simplify.
Pinstripe pants are incredibly difficult to wear.  For one thing, pinstripes are traditionally a business pattern.  For another, they’re traditionally limited to suits.  So pinstripe odd trousers are very limiting.
Focus your money on flexible basics.  Oxfords are great.  So are solid color t-shirts.  Good blue jeans.  Converse Jack Purcells.  Get to the other stuff once you have a foundation.

Q and Answer

Sam writes:

Having (relatively) recently graduated high school, I have decided that I have crossed the threshold into adulthood, and I would like to dress the part. However, for as long as I can remember, I’ve been wearing graphic t-shirts and the same five or six pairs of jeans which are covered in god-knows-what of irremovable stains.

During what I want to say was August, a French Connection retailer was having an end of summer sale, so I grabbed a white oxford and some pinstripe slacks which I have fallen in love with and want every excuse to wear.  Now, I am at a point where I don’t know what my next purchase should be. I can’t buy an entire ensemble due to my lack of funds, but I want to make one solid purchase. Something that will be that one bridge from my adolescence pile of clothes to a gentleman’s wardrobe.

First of all, you’re still college aged.  There’s no need to be Alex P. Keaton and wear a suit to class.

I’d focus on upgrading your casual wardrobe.  Don’t wear stained clothes.  Whatever clothes you have that have stains, give them to the goodwill or use them as rags.  Get yourself something plain that fits, even if it’s some t-shirts from Target.  Get yourself a decent pair of blue jeans - Levi’s 514s or 501 shrink-to-fits are a good starting point.  Maybe a pair of slim-fitting J. Crew or Canvas chinos.  Simplify, simplify, simplify.

Pinstripe pants are incredibly difficult to wear.  For one thing, pinstripes are traditionally a business pattern.  For another, they’re traditionally limited to suits.  So pinstripe odd trousers are very limiting.

Focus your money on flexible basics.  Oxfords are great.  So are solid color t-shirts.  Good blue jeans.  Converse Jack Purcells.  Get to the other stuff once you have a foundation.