Suits
As executive director of the Joffrey Ballet, Christopher Clinton Conway has to look buttoned-up. Luckily, he loves a good suit—and there’s one label he particularly favors. “I am a Paul Stuart devotee,” Clinton Conway gushes. He especially likes the brand’s Phineas Cole line, which boasts slimmer, more contemporary silhouettes. This year Conway purchased two suits: the Clive is an eight-button, double-breasted style in grey Italian wool flannel. The Doyle suit has a chalk-stripe pattern and a six-button, double-breasted jacket.
Wool Flannel Clive Suite, Phineas Cole ($1,897). Paul Stuart, 107 E. Oak St., 312-640-2650
Suits
Meanwhile, Jason Berngard, director of sales for Gilt City Chicago, goes bespoke when it comes to suiting. This year he purchased two (one light charcoal gray, the other navy) from Balani Custom Clothiers in Italian wool flannel. But Berngard’s custom suits are truly wardrobe investments. “I like to purchase a couple [of] fitted seasonal suits and wear them as separates by mixing them with everything in my closet,” he says.
Custom Suit, Balani (appx. $795). 55 W. Monroe St., 312-985-0868
Casual Wear
Things are a little more laid-back in the restaurant business—that’s why Arturo Gomez, president and partner of Rockit Ranch Productions, says his favorite sartorial purchase this season was his tweed sport coat from Haberdash.
Harris Tweed Blazer, Southwick ($878). Haberdash Bespoke, 607 N. State St., 312-624-8551
Casual Wear
Even if you work for a style-focused site, you can still go casual, fashionably. Berngard’s favorite everyday pieces include J.Brand slim straight corduroys, which he purchases from Gilt City’s sister site Park & Bond in burgundy and navy. He also loves J.Crew’s v-neck merino sweaters—although wool, the sweaters are lightweight enough to layer under a sports jacket like the one Gomez loves.
Slim Merino V-Neck Sweater, J.Crew ($78). 900 N. Michigan Ave., 312-751-2739
Shoes
Todd Heiser, design director of global architecture at Gensler, enthusiastically subscribes to one of fashion’s most oft-repeated maxims: No outfit is complete without the perfect pair of shoes. As summer turns to fall—and fall turns to winter—Heiser sports past-the-ankle, snowdrift-blocking, high-top sneakers. “I think every guy should have a pair of [Maison] Martin Margiela sneakers,” he says. “I bought a pair of paint-splattered trainers; people stop me on the street and ask me if I made them myself! I love that.”
Paint Splatter High Top Sneaker, Maison Martin Margiela ($565). Barneys New York, 15 E. Oak St., 312-587-1700
Shoes
Of course, paint-splattered sneakers aren’t for everyone—and unless you’re in the creative industry, they probably aren’t office-appropriate. Michigan Avenue editor-in-chief J.P. Anderson sports a more practical boot. “I recently picked up a pair of black Prada boots at Saks, and I’ve been wearing them everywhere,” he says. “Classic lines, forward-thinking style—they’re perfect.”
Spazzolato Wing-Tip Chelsea Boot, Prada ($750). Saks Fifth Avenue, 700 N. Michigan Ave., 312-944-6500
Accessories
Dan Uslan, Midwest president and publisher of Michigan Avenue, is always dressed to the nines, whether he’s attending/hosting a party, or sitting in on a sales meeting. But what really takes his outfits to the next level are the accessories. “I love the selection of cufflinks at Neiman Marcus,” he says. It’s Stephen Webster links that particularly catch Uslan’s eye: this season there’s nothing better than a mother-of-pearl pair.
Mother-of-Pearl Cufflinks, Stephen Webster ($325). Neiman Marcus, 737 N. Michigan Ave., 312-642-5900
Accessories
As for a manly bag to carry all your essentials, “I think every man should have a black leather tote,” Heiser muses. And although he has a trend prediction—“I'm done with messenger bags. I think a bag with handles is much more sartorial”—Heiser admits you don’t have to buy new every season. “I have [a bag] from Balenciaga that is two years old,” he says. “It just gets better with age.”
Arena Mini Folder, Balenciaga ($1,095). Barneys New York, 15 E. Oak St., 312-587-1700
