Dress Sneakers: Office Style Options by Luxury Brands, Fashion Designers

Throw out those Seinfeld Nikes and invest in a pair of grown-up kicks

Paul Smith White Lokai Trainers, $210 (paulsmith.co.uk) - Richard Chai blazer, $423, and pants, $294; Siki Im shirt, $245; H&M silk tie, $24.95; Styling by Shibon Kennedy
Photograph by Jeremy Liebman for Bloomberg Businessweek

Casual Friday. It began as a reward for having to dress so seriously the other four days of the week. It permits men who know, more or less, how to wear a business suit to arrive at work in a Hawaiian shirt. It allows clean-cut professionals to relax a little. On Thursdays, Joe in acquisitions is Romney; on Friday, he’s Jerry from Seinfeld. It’s not simply the jeans with the high waist. It’s the sneakers. God, those sneakers—two big, basic blocks that veer from the athletic to the orthopedic. They’re a blinding distraction, like teeth that have just been bleached (although at least that guy can close his mouth). The persistent thought is that there has to be a better way.

And now there is: dress sneakers. Everyone from Banana Republic at the lowish end ($98) to Balenciaga in the upper echelons ($515) has a dress sneaker this season. Ideally, they’re a flat-soled, high-top affair (Banana’s are low) with enough design to suggest expensiveness, but not so much that you look gaudy. Pair them with jeans, and you’re the coolest guy at after-work drinks. Wear them with a suit, and you’re a maverick.

Since 1995, when the Air Jordan XI became the first basketball shoe to feature patent leather, men have been flirting with sneakers as officewear. “That was the era when kids began wearing sneakers to prom, and then to job interviews,” says Elliott Curtis, professor of Sneakerology, an actual course taught at Carnegie Mellon University. “That’s when they become almost formal and acceptable.”

Michael Jordan retired for good in 2003, and by then the trend of wearing sneakers to work—after a detour into Skechers and Jack Purcells—had cooled. Yet in the past 10 years, the relative sartorial lawlessness of hoodie-wearing techies has given the larger, more staid business world an opportunity to rethink how to do casual with dignity (or at least panache).

Good dress sneakers take the cool of a pair of Jordans in a more chic, adult direction. They’re popular among basketball stars such as Carmelo Anthony, Amar’e Stoudemire, and Dwyane Wade, who’ve worn dress sneakers on their way into the stadium. The appeal, in part, is that luxury brands have gotten in on the act. “These sneakers have become so expensive that for an ad guy or a nonbanker, they’re a way of saying, ‘I’ve got cash,’ ” says Mordechai Rubinstein, founder of the Mister Mort fashion blog.

Sensing this, mass-market houses have been turning to superdesigners to attract high-end consumers. Punk designer Jeremy Scott is working with Adidas. Converse is collaborating with menswear staple John Varvatos on the reissue of the Converse Weapon, which sells for $250. New Balance has enlisted Japanese designer Junya Watanabe for its 1600 model. Nike has its Kanye West-designed Air Yeezy; they retail for $300, if you can find them.

According to NPD Group, a market-research firm, the so-called classic sneakers category, which includes higher-end dress sneakers, is now among the fastest-growing segments of the $13.8 billion athletic footwear industry, outpacing basketball and running. Yet where I live in Boston, I’ve seen very few people going anywhere in a pair of dress sneakers—they wear loafers or Topsiders or those things that Rockport and its competitors make that are somewhere between a dress shoe and a mountain boot. On Fridays there’s still a parade of guys heading to work in Seinfeld’s dorky white kicks. The men you see in dress sneakers are invariably trendsetters from Asia, Europe, and South America.

To us, a sneaker signifies play. It’s not a serious shoe. It’s juvenile. In America, there’s a clear line between what an athlete wears and what a businessman does. They represent distinct institutions. In American basketball and baseball, the uniforms have become bigger and baggier. In soccer—and in rugby, another sport with only a vague noncollegiate presence in the U.S.—the clothes have continued to shrink. We just don’t have the same comfort with sharpness and fit as the elite soccer-playing countries. That deserves to change.

“Last year at Bread & Butter, a fashion industry trade show, I saw a lot of seersucker suits worn with bright-yellow high-tops,” says Simon Wood, founder and editor of Sneaker Freaker magazine. “We’re moving back into a crazier sort of basketball-sneaker-and-suit pairing again.”

You don’t have to go quite that far. Start with a pair from Paul Smith, the company that’s struck the smartest balance between sportiness and suavity, wit and wearability: wingtip tennis shoes and basketball shoes with great, high-quality leather in deep, rich colors. They’re not as blingy as a pair of Maison Martin Margielas, or as ornate as Balenciagas, or as ridiculously expensive as a pair of Bottega Venetas or Lanvins. Companies such as Paul Smith, and more overtly humorous designers such as Pierre Hardy, invite you to upgrade; they don’t intimidate. A lot of these sneakers actually look smarter worn with a suit than with a pair of jeans. The appeal is their amphibiousness—wear them to the office, wear them to a party. There’s nothing to fear.

However incrementally, your stylishness will increase the odds of your officemate arriving to work in a pair of Alexander McQueen or Jimmy Choo sneakers. And not just on Friday.

Photograph by Jeremy Liebman for Bloomberg Businessweek; Set design by We Are Rocket Science