Easy Ways to Look Better in Tailored Clothing
Whether you’re into the “coat-and-tie look” or not, most of us have to wear a suit at some point, and for those times, it’s amazing how much can be done with just a few basic steps. Look at the photo above, for example – two men in suits, but wearing them to very different effects. The man on the left looks great. The man on the right … less great. So much can be done with just a few simple changes. 
Get Your Pants Hemmed
You want your pants hemmed so that there’s either one break, or no break (a break is the small indentation on your pants as your cuff “breaks” over the top of your shoe). You may find, however, that even with properly hemmed trousers, you pants will slip down a little throughout the day, which will ruin those clean, vertical lines. Some simple solutions: wear suspenders, which will keep your pants up at all times; get your waistband and belt adjusted by a tailor, so they fit you better (although, you’ll always experience some slippage with belted trousers); or simply, pay attention to where your pants are and pull them up when need be.
Show a Bit of Cuff
You want about a quarter-of-an-inch of shirt cuff to peek out from your jacket sleeve. There are, however, some complications with this.
First, if your shirtsleeves are too long, you probably don’t want to shorten them. Shirtsleeves need to be a bit long, so that the cuff doesn’t ride up on you as you extend your arm (think of it as having some slack). Instead, you just want your cuffs to stay in the same position, regardless of how you move around. To achieve this, bring your shirt to an alterations tailor and have him or her tighten or loosen the cuff by moving the cuff button. It shouldn’t cost more than a couple of bucks.
Second, if your jacket sleeves are too short or long, you’ll need to have a tailor either let out some material from the edge or take your sleeves up from the cuff. The second process can be complicated by “working buttonholes,” where the buttonholes are actually punched through and not just for show. Don’t skimp here and let that last button sit too close to your sleeve edge. Instead, have your tailor take the sleeve up from the armhole, but know that it’ll add to the cost.  
Wear Better Shoes
Finally, wear better shoes. Ones that are made from full grain leather, not corrected grain. Cheap shoes look bad when they’re new, and worse with wear. Luckily, the market for good, full-grain leather shoes has gotten a lot more competitive over the years, which means the entry price has dropped to about $200. You can start with this list of good brands. I’d add Jack Erwin to that now, although I think you still get a nice jump in quality as you move from them to Meermin, Herring, or Loake (conversely, Jack Erwin is located in the US, so it’s a lot easier to return shoes if need be). If $200 is too much for you, there’s always eBay and thrifting. For eBay, you can use our customized search link or smart shop smartly for Ralph Lauren. To learn how to thrift better, check out Jesse’s three-part guide. 
Doing just those three things won’t make you look like Cary Grant, but they’ll make you look better than most suit-wearing people in the world. To look even better, read Jesse’s very reasonable and easy tips here. To look even better still, learn about the fit and silhouette of tailored clothing.
(Photo via White Hawk Warrior)

Easy Ways to Look Better in Tailored Clothing

Whether you’re into the “coat-and-tie look” or not, most of us have to wear a suit at some point, and for those times, it’s amazing how much can be done with just a few basic steps. Look at the photo above, for example – two men in suits, but wearing them to very different effects. The man on the left looks great. The man on the right … less great. So much can be done with just a few simple changes. 

Get Your Pants Hemmed

You want your pants hemmed so that there’s either one break, or no break (a break is the small indentation on your pants as your cuff “breaks” over the top of your shoe). You may find, however, that even with properly hemmed trousers, you pants will slip down a little throughout the day, which will ruin those clean, vertical lines. Some simple solutions: wear suspenders, which will keep your pants up at all times; get your waistband and belt adjusted by a tailor, so they fit you better (although, you’ll always experience some slippage with belted trousers); or simply, pay attention to where your pants are and pull them up when need be.

Show a Bit of Cuff

You want about a quarter-of-an-inch of shirt cuff to peek out from your jacket sleeve. There are, however, some complications with this.

First, if your shirtsleeves are too long, you probably don’t want to shorten them. Shirtsleeves need to be a bit long, so that the cuff doesn’t ride up on you as you extend your arm (think of it as having some slack). Instead, you just want your cuffs to stay in the same position, regardless of how you move around. To achieve this, bring your shirt to an alterations tailor and have him or her tighten or loosen the cuff by moving the cuff button. It shouldn’t cost more than a couple of bucks.

Second, if your jacket sleeves are too short or long, you’ll need to have a tailor either let out some material from the edge or take your sleeves up from the cuff. The second process can be complicated by “working buttonholes,” where the buttonholes are actually punched through and not just for show. Don’t skimp here and let that last button sit too close to your sleeve edge. Instead, have your tailor take the sleeve up from the armhole, but know that it’ll add to the cost.  

Wear Better Shoes

Finally, wear better shoes. Ones that are made from full grain leather, not corrected grain. Cheap shoes look bad when they’re new, and worse with wear. Luckily, the market for good, full-grain leather shoes has gotten a lot more competitive over the years, which means the entry price has dropped to about $200. You can start with this list of good brands. I’d add Jack Erwin to that now, although I think you still get a nice jump in quality as you move from them to Meermin, Herring, or Loake (conversely, Jack Erwin is located in the US, so it’s a lot easier to return shoes if need be). If $200 is too much for you, there’s always eBay and thrifting. For eBay, you can use our customized search link or smart shop smartly for Ralph Lauren. To learn how to thrift better, check out Jesse’s three-part guide

Doing just those three things won’t make you look like Cary Grant, but they’ll make you look better than most suit-wearing people in the world. To look even better, read Jesse’s very reasonable and easy tips here. To look even better still, learn about the fit and silhouette of tailored clothing.

(Photo via White Hawk Warrior)

A Summertime Favorite: Penny Loafers
Once the weather warms up and the days get long, I often find that the best shoes are either sneakers or slip-ons. I typically wear sneakers with jeans and casual outerwear, and slip-ons with dressier trousers and sport coats. Styles can really range, but most of the time, sneakers tend to be white and minimalistic, and the slip-ons tend to be penny loafers.
The penny loafer is often thought of as a quintessentially American shoe — a style that’s most at home with tweed jackets and Shetland sweaters, as they were originally worn on Ivy League campuses in the mid-20th century. Today, however, you can safely wear them without any preppy connotations (although, you can also wear them as such, if you wish). With a sleeker pair of European pennies, for example, you can combine them with a soft-shouldered sport coat, wool trousers, and an open collared shirt for a very dégagé Continental look. With some beefroll loafers, jeans, and a light jacket, you can go back to looking like an American, but in a way that doesn’t feel too preppy. 
If you haven’t yet got yourself a pair, consider some of these:
Highly expensive at $750+: JM Weston’s 180 moccasin and John Lobb’s Lopez are pretty iconic, with the first having uniquely high walls around the toe that help distinguish it from the pack. My favorite loafers in this price tier, however, are all from Edward Green – an English firm known for its tasteful designs, quality construction, and beautiful finishing. Check out the Piccadilly, Montpellier, Sandown, and Harrow to start.
Pricey options between $350 and $500: Less expensive, but no less well-made, are loafers from all of your usual suspects. Carmina, for example, has something that looks very much like Edward Green’s Montpellier, while Alden has a wide range of handsome American designs. More recently, Wildsmith (a bespoke shoemaker once famous for their unlined loafers) relaunched as a ready-to-wear brand, and although their loafers aren’t as close to their originals as Edward Green’s Harrow, they’re priced competitively. Shipton & Heneage will also have a nice range of options, and they’re made a bit more affordable through the company’s Discount Club. Additionally, Crockett & Jones is very much worth a look, as are Alfred Sargent, Sid Mashburn’s house line, Kent Wang’s antique calf loafers, and the newly launched Paul Evans.
A bit more affordable at $350 and below: Of course, for more affordable shoes, there’s always Allen Edmonds’ factory second store, where the company heavily discounts shoes that didn’t pass quality control. Flaws are often very, very minor, if even visible at all. Loake’s 1880 line is also worth a look, and they sometimes produce for Charles Tyrwhitt and Herring (just note that some Loake-made shoes aren’t of terribly good quality, so use good judgment). Similarly, Ralph Lauren and Brooks Brothers will have some nice models, even though their quality can really range. Stick to the stuff that retails for $350 and above, and wait for end-of-season sales. In addition, Meermin offers some of the best price-to-value ratio right now in footwear, especially once you take into consideration their made-to-order program, and Jack Erwin is the best I’ve seen in the sub-$200 price range. For more American styled loafers, check out Rancourt and Bass’ Made in Maine collection.
Shell cordovan: Lastly, shell cordovan loafers are worth highlighting. Although shell cordovan is traditionally a workboot material, it works wonderfully today for slightly dressier styles (think wingtips, tassel loafers, and penny loafers). Alden’s Leisure Handsewn is a really beautiful American model, while Carmina will be more European. Meermin may also be able to make you something through their made-to-order program.
(Pictured above: Hooman Majd in his fifteen year old Edward Greens)

A Summertime Favorite: Penny Loafers

Once the weather warms up and the days get long, I often find that the best shoes are either sneakers or slip-ons. I typically wear sneakers with jeans and casual outerwear, and slip-ons with dressier trousers and sport coats. Styles can really range, but most of the time, sneakers tend to be white and minimalistic, and the slip-ons tend to be penny loafers.

The penny loafer is often thought of as a quintessentially American shoe — a style that’s most at home with tweed jackets and Shetland sweaters, as they were originally worn on Ivy League campuses in the mid-20th century. Today, however, you can safely wear them without any preppy connotations (although, you can also wear them as such, if you wish). With a sleeker pair of European pennies, for example, you can combine them with a soft-shouldered sport coat, wool trousers, and an open collared shirt for a very dégagé Continental look. With some beefroll loafers, jeans, and a light jacket, you can go back to looking like an American, but in a way that doesn’t feel too preppy. 

If you haven’t yet got yourself a pair, consider some of these:

  • Highly expensive at $750+: JM Weston’s 180 moccasin and John Lobb’s Lopez are pretty iconic, with the first having uniquely high walls around the toe that help distinguish it from the pack. My favorite loafers in this price tier, however, are all from Edward Green – an English firm known for its tasteful designs, quality construction, and beautiful finishing. Check out the Piccadilly, Montpellier, Sandown, and Harrow to start.
  • Pricey options between $350 and $500: Less expensive, but no less well-made, are loafers from all of your usual suspects. Carmina, for example, has something that looks very much like Edward Green’s Montpellier, while Alden has a wide range of handsome American designs. More recently, Wildsmith (a bespoke shoemaker once famous for their unlined loafers) relaunched as a ready-to-wear brand, and although their loafers aren’t as close to their originals as Edward Green’s Harrow, they’re priced competitively. Shipton & Heneage will also have a nice range of options, and they’re made a bit more affordable through the company’s Discount Club. Additionally, Crockett & Jones is very much worth a look, as are Alfred Sargent, Sid Mashburn’s house line, Kent Wang’s antique calf loafers, and the newly launched Paul Evans.
  • A bit more affordable at $350 and below: Of course, for more affordable shoes, there’s always Allen Edmonds’ factory second store, where the company heavily discounts shoes that didn’t pass quality control. Flaws are often very, very minor, if even visible at all. Loake’s 1880 line is also worth a look, and they sometimes produce for Charles Tyrwhitt and Herring (just note that some Loake-made shoes aren’t of terribly good quality, so use good judgment). Similarly, Ralph Lauren and Brooks Brothers will have some nice models, even though their quality can really range. Stick to the stuff that retails for $350 and above, and wait for end-of-season sales. In addition, Meermin offers some of the best price-to-value ratio right now in footwear, especially once you take into consideration their made-to-order program, and Jack Erwin is the best I’ve seen in the sub-$200 price range. For more American styled loafers, check out Rancourt and Bass’ Made in Maine collection.
  • Shell cordovan: Lastly, shell cordovan loafers are worth highlighting. Although shell cordovan is traditionally a workboot material, it works wonderfully today for slightly dressier styles (think wingtips, tassel loafers, and penny loafers). Alden’s Leisure Handsewn is a really beautiful American model, while Carmina will be more European. Meermin may also be able to make you something through their made-to-order program.

(Pictured above: Hooman Majd in his fifteen year old Edward Greens)

How Much Should You Spend on Dress Shoes?
One of the questions I frequently get in my inbox is: “I’m looking to buy a better pair of dress shoes, and only have X to spend. Should I save up for something better, or is so-and-so brand OK?” Like with many questions we get, a lot depends on the person asking.  
It’s worth noting, however, that in footwear (like in everything), there are serious diminishing returns after a certain point. Very roughly speaking, that point tends to be around $350 at full retail, although what’s sold at full retail can be had for less with smart shopping (eBay, factory seconds, seasonal sales, thrift stores, etc).
The Unfortunate Reality of Diminishing Returns
There are a number of things that go into the construction of a good shoe, but the two biggest are: the quality of the leather used and how the soles have been attached. Jesse did a great job in describing the difference between corrected grain and full grain leathers here. It’s also worth noting that even among full-grain leathers, there can be differences in quality. Additionally, most well made shoes will have their shoes attached through a Goodyear or Blake stitching process. Jesse reviewed some of these in the second episode of our video series, and you can read more about each technique here. The short of it is: with a sole that’s been stitched on, rather than glued, you can more easily resole your shoes, which means you don’t have to bin them when the bottoms wear out.
In the past, the “entry price” for good (dress) shoes tended to be around $350. These were usually from Allen Edmonds, Ralph Lauren, and Brooks Brothers, although not everything from these brands were worth buying. There were also some European names such as Herring and Loake’s 1880 line.
After this, you get marginally better constructions, but the differences become smaller and smaller (perhaps a leather insole vs. a fiberboard insole, or a sole that’s been attached by hand rather than machine, or slightly better leathers used for the uppers). Largely, as you move up from the $350 MSRP mark, you’re paying for design. A $1,250 pair of Edward Greens won’t last you 4x longer than a $350 pair from Allen Edmonds, but to many, they’re shaped and finished more handsomely.
The Emergence of a More Competitive Market
The good news is that the market has gotten a lot more competitive in the last five years, and the cost/ benefit curve has smoothed out considerably. Today, there are companies such as Beckett Simonon, John Doe, and Jack Erwin below the $200 price mark (the last of which I was particularly impressed by). Just a hair over $200 is Meermin, which I still think is one of the best values for (relatively) affordable footwear. They have a “Classic” line for about $200 (but with customs and duties, you might pay around $230) and a higher end “Linea Maestro” line for about $300 starting. And at the $350 mark, there’s more than Allen Edmonds and Loake’s 1880 these days. Paul Evans, Kent Wang, and Howard Yount are all good companies to look into.
The question of how much should you spend isn’t about what’s “good” in the footwear market, it’s about what’s “good enough” for you. For dress shoes, the only real criteria are: quality full-grain leather uppers and some kind of stitched on sole. Much of the rest is about aesthetics and personal preference.
(Photo: Crockett & Jones’ Whitehall oxfords at Ben Silver)

How Much Should You Spend on Dress Shoes?

One of the questions I frequently get in my inbox is: “I’m looking to buy a better pair of dress shoes, and only have X to spend. Should I save up for something better, or is so-and-so brand OK?” Like with many questions we get, a lot depends on the person asking. 

It’s worth noting, however, that in footwear (like in everything), there are serious diminishing returns after a certain point. Very roughly speaking, that point tends to be around $350 at full retail, although what’s sold at full retail can be had for less with smart shopping (eBay, factory seconds, seasonal sales, thrift stores, etc).

The Unfortunate Reality of Diminishing Returns

There are a number of things that go into the construction of a good shoe, but the two biggest are: the quality of the leather used and how the soles have been attached. Jesse did a great job in describing the difference between corrected grain and full grain leathers here. It’s also worth noting that even among full-grain leathers, there can be differences in quality. Additionally, most well made shoes will have their shoes attached through a Goodyear or Blake stitching process. Jesse reviewed some of these in the second episode of our video series, and you can read more about each technique here. The short of it is: with a sole that’s been stitched on, rather than glued, you can more easily resole your shoes, which means you don’t have to bin them when the bottoms wear out.

In the past, the “entry price” for good (dress) shoes tended to be around $350. These were usually from Allen Edmonds, Ralph Lauren, and Brooks Brothers, although not everything from these brands were worth buying. There were also some European names such as Herring and Loake’s 1880 line.

After this, you get marginally better constructions, but the differences become smaller and smaller (perhaps a leather insole vs. a fiberboard insole, or a sole that’s been attached by hand rather than machine, or slightly better leathers used for the uppers). Largely, as you move up from the $350 MSRP mark, you’re paying for design. A $1,250 pair of Edward Greens won’t last you 4x longer than a $350 pair from Allen Edmonds, but to many, they’re shaped and finished more handsomely.

The Emergence of a More Competitive Market

The good news is that the market has gotten a lot more competitive in the last five years, and the cost/ benefit curve has smoothed out considerably. Today, there are companies such as Beckett Simonon, John Doe, and Jack Erwin below the $200 price mark (the last of which I was particularly impressed by). Just a hair over $200 is Meermin, which I still think is one of the best values for (relatively) affordable footwear. They have a “Classic” line for about $200 (but with customs and duties, you might pay around $230) and a higher end “Linea Maestro” line for about $300 starting. And at the $350 mark, there’s more than Allen Edmonds and Loake’s 1880 these days. Paul Evans, Kent Wang, and Howard Yount are all good companies to look into.

The question of how much should you spend isn’t about what’s “good” in the footwear market, it’s about what’s “good enough” for you. For dress shoes, the only real criteria are: quality full-grain leather uppers and some kind of stitched on sole. Much of the rest is about aesthetics and personal preference.

(Photo: Crockett & Jones’ Whitehall oxfords at Ben Silver)

$195 Shoes from Jack Erwin

A couple of months ago, a reader asked me on Twitter what I thought of Jack Erwin’s shoes. Having never heard of the brand, I checked out their website and was intrigued by the value proposition: full-grain, Blake stitched shoes, shipped to your door for $195. There was even an offer for free returns. I went ahead and bought a pair for myself, and they arrived last month. 

These are really nice shoes for their price point, and it’s encouraging to see such good value being offered in this price tier. In the past, it used to be that to get well-made shoes for under ~$200, you’d have to hunt on eBay, thrift, or find Allen Edmonds’ factory seconds on sale. Now there are other options.

Jack Erwin’s shoes are fully made in Portugal from Portuguese tanned leathers. The soles have been attached using a Blake stitching method, which allows them to be more easily resoled than cemented shoes. The upside to Blake stitching is that it produces a thinner, lighter sole. This helps gives the soles a certain “sleekness,” which in this case nicely complements Jack Erwin’s handsomely shaped uppers. The downside is that Blake stitched soles are a bit easier to soak through in the rain than Goodyear welted ones (or even Blake-Rapid, which is a slightly different construction). Jack Erwin’s soles have a hidden channel at the bottom, which can help prevent this, but that cover will wear down over time, thus bringing us back to square one. That said, I have a few Blake stitched  shoes in my closet and wear them regularly. The differences between Goodyear welted and Blake stitched shoes can sometimes be overstated, and at the end of the day, they’re both good constructions. 

Naturally, at this price point, one should expect some compromises. The quality of shoes can’t be easily read off buzz phrases such as “full grain leather upper” and “Blake stitched construction.” Just as important, if not more important, is the quality of the materials used. The quality of Jack Erwin’s uppers, lining, insole, and outsole aren’t as nice what you’d find on more expensive brands, such as Allen Edmonds and Crockett & Jones. How they’ll actually age in 5-10 years is anyone’s guess. And, while we’re quibbling, I wish Jack Erwin didn’t advertise their outsoles as being hand stitched when they’re clearly not. I assume by “hand stitched,” they mean someone operated the (Blake) machine by hand, which is not an uncommon usage of the term nowadays, though I still think it’s misleading.

Nevertheless, I’m pretty impressed. There are dozens of brands in the US right now selling $200 shoes that aren’t anywhere near as nice, and you can find them in all the major department stores. Compared to many of their direct competitors, Jack Erwin’s shoes are well made, handsomely styled, and offer much better value. That’s something to be applauded.  

(Photos via Jack Erwin)