For many guys, when it comes to uncomfortable situations, asking another man for style advice is up there with having your annual medical screened live on YouTube. Which is why we did the asking for you. Here’s what some of the best-dressed men in the fashion business said when we asked for tricks of the trade we all could learn from.
Simon Crompton: Founder, Permanent Style
Many of my readers ask about jackets to buy after the ubiquitous navy blazer. It’s so much harder than picking suits. Perhaps surprisingly, my top recommendation is something in a pale oatmeal color. It’s smart enough for the office because it’s muted and plain, yet it’s definitely not a blue or gray. Goes with almost any shirt and trouser, too.
Matt Hranek: Editor, WM Brown Project
A good wax jacket like a Barbour (of any vintage) can take you from the field to a more formal setting without a hitch. It’s the perfect piece of outerwear.
Alexander-Julian Gibbson: Stylist
Never take yourself, or your clothes, too seriously. Even when I’m wearing a tuxedo, I’ll trade the dress shirt for a T-shirt or a silky button-down, and treat it all like any other outfit.
Justin Berkowitz: Men’s fashion director, Bloomingdale’s
I like trying to master the formal-informal mix by pairing (and hopefully balancing) more tailored elements with softer ones, so I feel comfortable. I’ll wear a blazer with a more casual trouser, like a pleated cotton chino. If I’m wearing a dressier wool trouser, I’ll balance it with a casual bomber jacket or overshirt. And if I’m wearing a suit, I’ll do it with a crewneck sweater and loafers instead of a shirt, tie and oxfords.
Alessandro Squarzi: Creative director, Fortela
The time has come for men to start dressing properly again and chicly. No more stretch-type trousers. The suit also needs to widen slightly, and the bottom of trousers must be no less than 20 cm wide. I love to wear a suit with a polo underneath—I think this looks very elegant.
Mark Cho: Founder, the Armoury; co-owner, Drake’s
Black knit ties are one of my favorite things, evoking Miles Davis from the ’60s. While the obvious choice is to wear it with a gray suit and white shirt, I would suggest trying it with neutral jackets instead. It’s a great way to take country colors and give them a twist for the city.
Philip Conradsson: Freelance writer and menswear consultant
A lot of men really take their time to make alterations for their suits but totally forget about their coats. In my opinion, it doesn’t matter how good your suit looks if the coat has a poor fit. It almost always comes down to arm length and width around the waist. Think of what you want to wear underneath the coat and adjust it after that; it’s worth the money every time.
Josh Peskowitz: Men’s fashion director, Moda Operandi; owner, Magasin
In the same way many guys wear blue and gray regularly, I turn to olive and brown. While it’s not as obvious, it is one of those sartorial color choices I consistently go back to.
Bruce Pask: Men’s fashion director, Bergdorf Goodman and Neiman Marcus
A charcoal gray is the best and easiest sneaker color because it goes with everything and it doesn’t match. Navy blends into denim too much, light gray is a bit too light, while white is bright and very poppy. But dark gray always works.
Aleks Cvetkovic: Style editor and Robb Report columnist
Play with texture, not pattern. If corporate pinstripes feel a little stiff and bold checks a touch shouty, softly textured jackets, shirts and accessories are a timely alternative. A flannel sport coat paired with a matte wool tie and a washed oxford button-down (like this Edward Sexton combination) is infinitely more sophisticated than menswear that shouts to get attention.
Olie Arnold: Style director, Mr Porter
Opt for a chunkier commando or crepe sole the next time you buy a pair of classic shoes, like derbies or penny loafers. If they’re cut from a leather in a versatile color, like brown, black or burgundy, you’ll get double the wear— they work well on and off duty.
Igee Okafor: Founder, Bond Official
Make loafers your friend because the best styles can be dressed up or dressed down. Penny loafers take a suit from day to night, but pair a tasseled loafer with any ensemble and you’re guaranteed an easy upgrade. It works as well with your classic crewneck sweater, shirt and trousers as it does with a pair of dark jeans and a T-shirt.
Andreas Weinås: Editor, King magazine
I always try to wear at least one solid garment and a patterned one in my outfits. Having too many patterns, especially around the face and torso (jacket, shirt and tie), can become quite overwhelming. At the same time, a look concocted without a single pattern or differences in texture can feel a bit dull.
Gianluca Migliarotti: Cofounder, trouser-maker Pommella Napoli
I always suggest trousers in lighter colors than the jacket, with very few exceptions. Especially if you are traveling, if you carry a blue blazer you can play with the color of your trousers and always look smart and different. I wear a lot of different colors: green, white, cream, red, beige, light gray, light blue…and so on.
David Coggins: Author and Robb Report columnist
A strategic baseball hat can be worn rarely and unexpectedly, such as at the Masters. When sports are involved, don’t fear the baseball hat—but leave it behind the rest of the time.