The other trick is this: Get an education in the fundamentals of menswear. We’re talking about tailoring that makes you look taller and more fit than your sweats, colors that look expensive and mash up in an endless number of ways, plus swaggy accessories that elevate your game, not drag everything down to little-brother territory. Once you know how to dress like a gentleman, once you can suit up like a pro, you can break every rule in the book. You won’t even need to take cues from an awards show. Check out our top styling tips and tricks--and then shop the latest modern gentleman essentials from Kenneth Cole.
Make Fit Your Top Priority
Good news for your 401(k): Owning a closet full of luxury clothes isn’t the best way to look like the classiest version of yourself. What really matters, what has always mattered, is how your clothes fit; the shoulder of your jacket, the sleeve of your shirt, the hem of your pants, the whole nine yards. Whether you’re into 2019’s slouchier fits or prefer slimmer cuts, making friends with a good tailor and learning how to talk about clothes so that you’re asking for the right adjustments is key to looking your best—not to mention feeling your most comfortable in formal clothes.
Fake Formality with Smart Colors
We believe in the power of a good suit, but no one wants to live in tailoring 24/7. To look like a world-class gentleman on your lowest-key days, stick with wardrobe classics like chinos and crewneck sweaters and T-shirts in sophisticated solid colors. Navy, olive, and burgundy are always a good bet and look much more expensive than any cheeky print or bright color in your closet. Stick with one color from head to toe and add on-point accessories, and you can let the day take you anywhere, from the dog park to a dinner party with the person you met at the dog park.
Buy Better Dress Shoes—More Than One Pair
You might not be able to judge a man by his shoes, but you can absolutely judge his sense of style by them. That’s why investing in a wardrobe of well-made classics is key. If you own only one do-it-all oxford that’s been re-soled a hundred times, you’re doing it wrong (also: ouch). You want to collect dress shoes like you collect sneakers: in a range of colors and styles so you can turn every outfit into a flex. Think: brogues, derbies, oxfords, and monk straps all in different colors, from black and brown—both caramel and chocolate—to blue and burgundy. (We've got a selection of some of our favorites from Kenneth Cole below.) Once your dress-shoe game is up to par with the rest of your style, nothing can stop you. Except maybe a street-style photographer.
Three Words: No-Show Socks
Smart trousers, chinos, and suits worn with dress shoes and bare ankles is a deeply cool look that will make you feel like an Italian hanging out at Pitti Uomo (always good). But wearing nice shoes without socks is a crime against comfort, not to mention a great way to ruin your favorite oxfords and alienate your roommates. No-show socks to the rescue. Sure, they’re not the prettiest sight on their own, but what they lack in cool factor they make up for in performance. Just make sure they’re truly no-show. Nothing bricks a man’s crossed-leg style game like a flash of cotton along the edge of his shoes. Bad taste is cool right now, but even that’s off limits.
