How to Dress Better as a Guy

One of the biggest roadblocks I run up against when advising guys on fashion is the idea that dressing well is somehow at odds with the rest of their lifestyles. Guys will claim that they’re too busy and poor to shop for new clothes. Or that they’re math grad students. Or that they live in San Francisco, where blazers are only worn ironically. But dressing well is not fundamentally about buying expensive brands or donning outlandish getups. I firmly believe that you can wear a hoodie every day and look put together, so long as it’s 1) the right fit for your body type and 2) of a consistent formality with the rest of your outfit.

I mention fit first because it’s both obvious and difficult. Style blogs hammer on fit. Men’s magazines hammer on fit. Yet fit is often hard to distinguish. Where is the line between body-skimming and skin-tight? Where should the cuff of your pants hit your foot? And what about all those trends – the baggy jeans trend, the oversized sweater trend, the boyfriend shirt trend – that seem predicated on, if anything, anti-fit?

My advice to you is to go to a local department store and get your measurements. Remember those salespeople who keep asking you if they can help you find the right size? They can! In fact, it’s their job! Try on different genres of clothing. Ask for opinions, and take any negative comments seriously. Don’t settle for “they’re a little too big, but my belt will take care of that.” Now memorize how the fabric sits on you. Are the pants low rise? How slim are they through the thigh? Numbers are imperfect – certain brands run small or large, some have slim fits – but if you have a pattern in mind, future purchases can essentially be a variation on a theme.

Of course, it’s possible that all your clothes are objectively the right size and they still don’t look great on you. At this point, I ask you to consider whether you have been dressing for your body type, a concept that the media has drilled into women, but not into men. For instance, I know that I’m a ruler. I’m narrow at the waist and narrow at the hips. Sofia Vergara is a classic hourglass, Beyonce is a triangle, and so on. Guys rarely have body type models pointed out so explicitly to them, and even more rarely are they told that they should be aware of it when they choose clothes. This is unfortunate, because fashion trends are not universally flattering. One shirt makes a guy look fat. Another makes him prosperous. This blog post gives a rough sketch of several prototypical male body types.

Finally, I think a lot of bad outfits are the result of misunderstanding the relative weight of each item of clothing and how they can be put together. For instance, a guy might wear a dress shirt with cotton twill pants and athletic sneakers. Individually, there’s nothing wrong with these articles of clothing. Together, though, it’s a terrible look. In every outfit, you should make sure that your clothes are consistently formal (or informal). To help you decipher which is which, I’ve created a table in ascending order of formality. Note that some articles of clothing span multiple levels. You can, for example, wear a polo shirt with jeans and sneakers to class, and a polo shirt with chinos and suede boots on a dinner date. A lot depends on the cut, wash, and material, and as you develop as a sartorialist, you’ll find that even certain combinations not sanctioned by the chart can work under the right conditions. After all, rules are meant to be broken, and what is style but the willingness, and the daring, to take those chances?






Shorts, Jeans

Hoodie, Sweater, Windbreaker

Flip Flops, Sneakers, Boots

Polo shirt

Jeans, Shorts

Hoodie, Sweater, Windbreaker, Sports Coat

Sneakers, Boots, Boat Shoes

Polo shirt


Sweater, Windbreaker, Sports Coat

Boots, Boat Shoes, Wingtips

Button-Down Shirt

Jeans, Chinos

Sweater, Sports Coat

Boots, Wingtips

Dress Shirt

Suit Pants

Suit Jacket

Dress Shoes