Photograph courtesy of ABC/Photofest
Asked in a recent survey about what they look for in clothes, men ranked comfort above everything else, including an outfit's ability to attract women and its ability to make you look better than the next guy. The pursuit of comfort, that core American value, brought us the La-Z-Boy with built-in fridge, the Clapper, and, in fashion, ripped jeans with a white T-shirt.
You can't knock a guy for wanting clothes that feel as good as a bacon cheeseburger tastes. After all, men—with the exception of Matthew McConaughey—are in clothes more than they're out of them. But dressing for comfort can breed bad habits, primarily laziness—and laziness quickly leads to shlubbiness.
Blame the Hollywood A-listers who've perpetuated the I've-just-rolled-out-of-bed-to-get-a-soy-latte ensemble of beat-up jeans, oversize sunglasses, and a tee with a plunging neckline. While Jude Law, Johnny Depp, Orlando Bloom, and Jake Gyllenhaal are often at their best when they're at their unfussiest, the same can't be said for most men. If you're not being chased by the paparazzi, you probably shouldn't attempt to emulate the carefree-celebrity look. That doesn't mean you have to Polaroid your closet and plan your outfits (trying too hard can be just as detrimental to your image), but it does mean you should be aware of the fine line between dressing casually (trim polos, tailored khakis, washed-cotton button-downs) and looking homeless.
Many men go their entire lives without discovering the right silhouette for their bodies. And even guys who think they know what fits correctly are usually off by a size. A T-shirt can be an upstanding garment, one that's multi-occasion-appropriate, when it's cut out of pima cotton, skims your frame, and falls just below your hips.
To counterbalance the laid-back sensibility of a henley and a hoodie, toss something that skews formal into the mix. Chocolate-brown wing tips help elevate worn-in jeans, while a black-faced watch dresses up a polo. And try throwing on a jacket. It doesn't have to be navy, and it doesn't have to be a blazer. A zipped cropped cotton jacket takes any outfit from undone to put-together.
Finally, move out of your comfort rut by exploring different styles from a brand you already trust. If you like the way a shirt from a certain label fits, you'll probably dig the way a suit from that brand falls. "You have to study. You have to shop," says Kanye West of the nuts and bolts behind his inimitable aesthetic. "Style is work." Courtney Colavita