“Maybe style has become ridiculously isolating these days. This is especially true for men, I think. And I don’t know exactly how I feel about it. On one hand, I’m very happy to see people with an interesting sense of style… On the other, sometimes style feels less like a fun, personal expression and more like a total disregard for people who might weigh more than you, or have less money for cell phone technology than you, or might be more than five years older than you.” — Todd Levin (the whole piece is very much worth your time) (Thanks, Will)

On the podcast Necessary & Sufficient, host Evan Forman sends his guests an envelope containing two index cards, each with a single word. They then open the envelope live on the air. When I appeared on episode 100 of the show, the words were “fashion” and “style.” A discussion followed.

"Nice Stuff, But Not for Me"
One of the most important skills you can learn as you develop your own sense of style is how to judge whether something fits you. I don’t mean just physically (though that’s critically important), but also whether something properly suits your personality, character, and lifestyle. For example, a cutaway collar might frame your face very well, but if you’re a stodgy academic who is hoping to be thought of as an intellectual, perhaps a button down collar is more suitable. 
Figuring out how clothes should fit is one thing; figuring out whether they suit your personality and character is something else entirely. That part requires a lot of self-discovery, honesty, and time. Unfortunately, when it comes to the task of finding clothes that suit your character, you can easily be distracted by barrage of blogs and magazines telling you what’s cool this season, what’s big in Japan, or how to pull off that “Italian sprezzatura" look that everyone is raving about. Couple that with professional product shots and good looking models, and you can be drawn to certain clothes for all the wrong reasons. 
One thing I’ve found helpful is to be conscious of whether you’re buying something just because it’s well designed. Remember that there are hundreds of good looking pieces every season. Indeed, there’s rarely a week that goes by where I don’t see at least five or six things that I think look great. However, just because a piece of clothing is well designed, and perhaps even fits you well, doesn’t mean you should buy it. You should stick to the task of developing a focused, coherent wardrobe that clearly express who you are, not just build a collection of good looking clothes. 
And although it’s counter intuitive, I’ve also found that it useful to have a very narrow and defined set of style heroes. People you think are maybe more aligned with your personality, character, and lifestyle than others. Of course, inspiration shouldn’t be the same as emulation, and at some point, you’ll naturally find your own voice, but it can be helpful to be clear about what looks you’re going for. 
Thoreau once said, “A man is rich in proportion to the number of things he can afford to let alone.” It’s important to recognize when something looks great, but isn’t necessarily right for you. Shop slowly, let your clothes reflect your body and personality, and know when to leave something alone. 

"Nice Stuff, But Not for Me"

One of the most important skills you can learn as you develop your own sense of style is how to judge whether something fits you. I don’t mean just physically (though that’s critically important), but also whether something properly suits your personality, character, and lifestyle. For example, a cutaway collar might frame your face very well, but if you’re a stodgy academic who is hoping to be thought of as an intellectual, perhaps a button down collar is more suitable. 

Figuring out how clothes should fit is one thing; figuring out whether they suit your personality and character is something else entirely. That part requires a lot of self-discovery, honesty, and time. Unfortunately, when it comes to the task of finding clothes that suit your character, you can easily be distracted by barrage of blogs and magazines telling you what’s cool this season, what’s big in Japan, or how to pull off that “Italian sprezzatura" look that everyone is raving about. Couple that with professional product shots and good looking models, and you can be drawn to certain clothes for all the wrong reasons. 

One thing I’ve found helpful is to be conscious of whether you’re buying something just because it’s well designed. Remember that there are hundreds of good looking pieces every season. Indeed, there’s rarely a week that goes by where I don’t see at least five or six things that I think look great. However, just because a piece of clothing is well designed, and perhaps even fits you well, doesn’t mean you should buy it. You should stick to the task of developing a focused, coherent wardrobe that clearly express who you are, not just build a collection of good looking clothes. 

And although it’s counter intuitive, I’ve also found that it useful to have a very narrow and defined set of style heroes. People you think are maybe more aligned with your personality, character, and lifestyle than others. Of course, inspiration shouldn’t be the same as emulation, and at some point, you’ll naturally find your own voice, but it can be helpful to be clear about what looks you’re going for. 

Thoreau once said, “A man is rich in proportion to the number of things he can afford to let alone.” It’s important to recognize when something looks great, but isn’t necessarily right for you. Shop slowly, let your clothes reflect your body and personality, and know when to leave something alone. 

Season 2, Episode 2: PTO Place: Jay Kos

From Put This On Season 2, Episode 2, a profile of New York menswear retailer Jay Kos. Kos is known for mixing traditional style with bold fabrics and colors, and is a favorite of contemporary dandies like Fonzworth Bentley.

From Season 2, Episode 2 of Put This On

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.

“The conspicuously well dressed man is not a well dressed man at all, but merely a block for displaying the best materials and the latest fashions upon. His clothes and all articles of outward attire cry out their quality, and forcibly draw attention to their very newest cut, set, twist, or turn; and you say “There’s a dressy man if you like! Everything right up to date, including the walking stick.” The really well dressed man attracts no such remark. Of him you are more likely to say, “That man looks very smart - for some reason or another. Wonder what it is!” You may depend upon it that the man of whom that is said is a man not only of fashion, but of something very important besides - namely, good taste, strong individuality, faithfulness to personal style.” Fashion, August 1899


Avoiding Buyer’s Regret
When you’re shopping for clothes, there are probably a dozen or more variables to consider before you make a purchase. Unfortunately, most of these considerations can get muddled, and if you don’t parse them out carefully, you can buy something for the wrong reasons. So I thought I’d rank some of the principle considerations: fit, style, construction, and branding, in that order. When deciding whether or not to buy something, go through these considerations in order of importance and you’ll minimize your likelihood of ending up with buyer’s regret. 
Fit
As they say, fit is king. The first thing anyone notices, even before style, is whether your clothes fit well. A man would look better in a well-fitting pair of jeans and a t-shirt before he would in a sloppy suit. 
What fits is what flatters. This point may seem basic, but it’s amazing how rarely you see it practiced. Men who aren’t style conscious tend to wear clothes too big, while men who pay a lot of attention often wear things too small. Proper fitting clothes hit in the right places and give you clean lines, no matter what your movement or position. Shoulder seams should end around the shoulder bone, and clothes shouldn’t be so baggy that they fold, nor be so tight that they pull. 
Style
Always remember that fit comes before style. There’s no quicker way to catch buyer’s regret than to buy something that’s stylish, but doesn’t fit perfectly. Once you find something that fits, however, consider whether the garment has all the design details you’re looking for. If you want something that will last, avoid things that veer too strongly towards one design trend. As a very general rule of thumb, I find simple, classic designs to be best. 
You may also want to consider how versatile the garment is. Basic blues, greys, and browns will help you build in that versatility, as all those colors are easy to incorporate. To be sure, there’s a lot of room for dark greens, burgundies, and other livelier colors. However, make sure you’re not buying something that you can only wear with one pair of trousers or one jacket. You should seek to build a wardrobe, not a collection of outfits.
Construction
Some may be surprised that I rank construction so low on the list of considerations. However, a garment’s design will always be the bigger determinant of its lifespan. Most clothes are made to last at least a couple of years now. If a jacket is made with skinny lapels, for example, its style will give out much sooner than its cloth. Thus, while I strongly believe people should invest in higher quality purchases, I also think that they should prioritize fit and style above quality. If it doesn’t look good on you or work with the rest of your wardrobe, the quality of its construction will mean very little.
Branding
Finally, there is branding. Everyone succumbs to this to some extent. We buy clothes partly to express the person we are, and partly the person we wish to be. We may also buy something because of the lifestyle it represents. It may not be the most “rational” of considerations, but it’s no less real or enjoyable. Clothes in this sense are romantic; they make life less dull. It would be crotchety to deny or condemn it. At the same time, you should be aware of what you’re doing, and only do so if it meets the other criteria above. 
Conclusion
Of course, ideally, you should make purchases that fulfill every one of these categories (with the exception of maybe branding). However, people have limited means, time, and patience for such things, and not everyone is going to spend the next few months searching for the perfect shirt. Thus, for the non-neurotic, you now have neatly parsed considerations that you can prioritize in order to make better buying decisions.
Purchase things for the right reasons. Buy something because it’s well-made before you buy into a brand; buy something well designed before you buy into its quality; most importantly, buy something because it fits well before you consider anything else.

Avoiding Buyer’s Regret

When you’re shopping for clothes, there are probably a dozen or more variables to consider before you make a purchase. Unfortunately, most of these considerations can get muddled, and if you don’t parse them out carefully, you can buy something for the wrong reasons. So I thought I’d rank some of the principle considerations: fit, style, construction, and branding, in that order. When deciding whether or not to buy something, go through these considerations in order of importance and you’ll minimize your likelihood of ending up with buyer’s regret. 

Fit

As they say, fit is king. The first thing anyone notices, even before style, is whether your clothes fit well. A man would look better in a well-fitting pair of jeans and a t-shirt before he would in a sloppy suit. 

What fits is what flatters. This point may seem basic, but it’s amazing how rarely you see it practiced. Men who aren’t style conscious tend to wear clothes too big, while men who pay a lot of attention often wear things too small. Proper fitting clothes hit in the right places and give you clean lines, no matter what your movement or position. Shoulder seams should end around the shoulder bone, and clothes shouldn’t be so baggy that they fold, nor be so tight that they pull. 

Style

Always remember that fit comes before style. There’s no quicker way to catch buyer’s regret than to buy something that’s stylish, but doesn’t fit perfectly. Once you find something that fits, however, consider whether the garment has all the design details you’re looking for. If you want something that will last, avoid things that veer too strongly towards one design trend. As a very general rule of thumb, I find simple, classic designs to be best. 

You may also want to consider how versatile the garment is. Basic blues, greys, and browns will help you build in that versatility, as all those colors are easy to incorporate. To be sure, there’s a lot of room for dark greens, burgundies, and other livelier colors. However, make sure you’re not buying something that you can only wear with one pair of trousers or one jacket. You should seek to build a wardrobe, not a collection of outfits.

Construction

Some may be surprised that I rank construction so low on the list of considerations. However, a garment’s design will always be the bigger determinant of its lifespan. Most clothes are made to last at least a couple of years now. If a jacket is made with skinny lapels, for example, its style will give out much sooner than its cloth. Thus, while I strongly believe people should invest in higher quality purchases, I also think that they should prioritize fit and style above quality. If it doesn’t look good on you or work with the rest of your wardrobe, the quality of its construction will mean very little.

Branding

Finally, there is branding. Everyone succumbs to this to some extent. We buy clothes partly to express the person we are, and partly the person we wish to be. We may also buy something because of the lifestyle it represents. It may not be the most “rational” of considerations, but it’s no less real or enjoyable. Clothes in this sense are romantic; they make life less dull. It would be crotchety to deny or condemn it. At the same time, you should be aware of what you’re doing, and only do so if it meets the other criteria above. 

Conclusion

Of course, ideally, you should make purchases that fulfill every one of these categories (with the exception of maybe branding). However, people have limited means, time, and patience for such things, and not everyone is going to spend the next few months searching for the perfect shirt. Thus, for the non-neurotic, you now have neatly parsed considerations that you can prioritize in order to make better buying decisions.

Purchase things for the right reasons. Buy something because it’s well-made before you buy into a brand; buy something well designed before you buy into its quality; most importantly, buy something because it fits well before you consider anything else.