I was resolute in not renting a tuxedo for my high school prom. I was also resolute in not wearing oxfords, derbies, or something of that ilk either. My reasoning—aside from it being the early 2000s, an era of all things baggy and questionable footwear—was that I didn’t want to be like everyone else. I still wanted to look presentable and in line with the prescribed dress code, but I also wanted to stand out. So, I got myself a silver-gray wool-silk blend gray suit from Calvin Klein Collection, one of the few labels that were making skinny silhouettes at the time. I paired it with a charcoal gray Merino wool sweater vest, crisp white dress shirt, and a periwinkle blue tie, also from Calvin Klein. My shoes? White leather dress sneakers.
This was the period before Normcore and long before the pandemic. It was a time when there was a whole catalog of fashion rules: what should and shouldn’t be worn for this occasion or that. And one of the major don’ts on that list was wearing sneakers to a dressy event. The horror! The shock! The utter disgust! None of that came my way. Instead, to my surprise, the reaction my fit received was overwhelmingly favorable. If there was an award for best-dressed of the night, it would have certainly gone to me on the sneakers alone.
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My kicks were clean, simple, elevated—all the characteristics befitting a dressy shindig. This is pretty much what sets dress sneakers apart from others in the same taxonomy. They weren’t gym shoes; they weren’t meant to be beat up; they weren’t wild and crazy, or bold and clunky either. They were elegant. I garnered a lot of oohs and aahs, perhaps because I was the only guy in sneakers at prom.
Now, sneakers and suits are pretty much standard. There are, however, a few scenarios when dress shoes should be considered over other styles, primarily if the event calls for a black or white tie. But come anything else, sneakers are downright acceptable. In fact, at a number of cocktail parties over the past few months, the amount of sneakers worn by men certainly outnumbered the dress shoes. And if you’re looking to follow in their footsteps, check out the swankiest, dressiest sneakers around—all of them made for a best-dressed list.
When it comes to footwear that's equal parts stylish, comfortable, and affordable, Florsheim often steals the show. Case in point: the brand's Heist sneaker, which features a polished leather upper in black and white, and a removable OrthoLite insole. This is what we call stealth, baby!
There's no shortage of white sneakers today—and that's great, cause they go with just about everything. But if you want something that feels distinct, but doesn't veer off the edge, take a look at Veja's V-10. The sneaker is just a little chunkier, with old-school paneling and careful branding details—like that "V" logo—that don't scream for attention, but don't fade into the background either.
Speaking of brands that emphasizes comfort, Cole Haan is the virtual master. The label continuously churns out dressy styles—from oxfords to derbies—that make strolling through the office or hitting the town a breeze. Take these leather wingtip sneaker (yes, wingtip sneakers!). From a distance, no one would be the wiser that these aren't traditional brogues.
The Royale is truly a sneaker for style kings. Prime example: Ryan Reynolds, a favorite among these parts, wore a the white version of Greats's stalwart sneaker with tailored navy trousers and a long-sleeve polo. This tan colorway is even dressier, and will pair nicely with something similar to Reynolds's fit, or with a beige or brown suit.
From linen and wool to cashmere and corduroy styles, Suitsupply really does live up to its name. Its stock is chock full of sharply tailored two- and three-pieces, dress shirts, and even footwear. The brand offer a head-to-toe look, and if a sneaker is your shoe of choice, you won't go wrong with this incredibly versatile suede sneaker. It goes with just about everything Suitsupply has to offer.
Made from Italian napa leather, Good Man Brand's low-tops most certainly have edge, and are not only good, but great. What’s more, three percent of the proceeds from each purchase will be donated to the Why Not You Foundation, an NGO that empowers and prepares kids to become the leaders of tomorrow.
Designer Jerry Lorenzo has made no secret of his ambitions to be the next Ralph Lauren. His signature sneakers, the 101, are sleek, subtle, and frequently sell out. So, if you want to start laying your own foundations, don't sleep when you find 'em in your size.
Raf Simons, one half of the duo behind Prada, has always marched to the beat of his own drum. He's the the kind of the designer that truly pushes boundaries, that takes fashion to the very edge without ever falling off. And this idea is exactly what these metallic sneakers represent.
Koio makes a completely minimalist sneaker, and it does it well. Though primarily known for its neutral-hued low-tops, it also has a full range of silhouettes, styles, and colors—all of which stay streamlined. The shoes are made in Italy, and the company was founded by Germans who are based in New York City. As a result, you're really getting the best perspectives (and access) possible.
Common Projects is patient zero for the current minimal-luxury-sneakers craze. The Achilles has become a holy grail for fervent fashion folk. Its cross-cultural appeal predated the muddled idea of throwing everything together, And it looks good with just about everything, especially a suit. Amongst a sea of competitors, it's a shoe has achieved that covetable status.
Maison Margiela's designer footwear legacy has remained relatively untouched. Its most prominent product is an upscale reinterpretation of a standard-issue German army trainer sneaker, done up in blue leather with suede accents and a gum sole. It's also been reinterpreted in numerous colorways and treatments, ranging from meticulous paint splatters to iridescent metallic leather and intricate basket-weave materials.
In Italy's shoe country, Santoni is making old-school luxury modern. Prime example: this monk strap sneaker—an incredibly unique hybrid—done up in rich blue suede. It is the kind of shoe that'll truly upgrade your fit while still providing you with comfort—and sentiment that you can take to the bank. To wit: just check out its name.
The brand may be best known for its supple Gommino driving loafers, but Tod's isn't a one-trick pony. Aside from great apparel, the Italian label also does chunky boots, sturdy lace-ups, and sneakers that run the gamut—from minimal to maximal as all hell. Take your pick, of course, but right now, for our money, this refined, tan, go-with-anything vibes of the Tabs sneakers are tough to beat.
The fields of Tuscany, the birthplace of Salvatore Ferragamo, are rich in romance and history. This is exactly the vibe that the brand brings to its vast selection of footwear, all of them crafted impeccably using the finest leathers and the finest dyes. They are the kinds of designs that don’t have tricks or gimmicks, there are no excessive flourishes. Simply, you have is a mighty fine shoe, built to last a very long time. Which is really all that you need.
The Gucci sneaker look is hard to mistake for anything else. It has the kind of standard Italian high-fashion take, with recurring motifs that are as widely recognized as the brand name. Gucci doesn't skimp out on styles, either. Although the embellished low-tops are a classic, the brand has also made waves with its chunky sneakers.