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? Read the rest of this entry »