Ace Your Date Night Look With Cole Haan’s 4.ZERØGRAND Stitchlite™ Oxford

Blue Oxford shoes surrounded by other clothing items on a grey background
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This article was produced in partnership with Cole Haan.

It’s Friday afternoon, and in a few hours, you’ve got a first date. Score! Everything’s going according to plan so far: The barbershop was able to squeeze you in to tame that unruly mop. You managed to nab the only available washer-dryer in your apartment’s laundry room and tackled two loads (two!) of dirty clothes. And you’ve just called up your favorite Italian restaurant—the one that makes all their pasta from scratch—and sweet-talked the maître d’ into reserving the best table in the house. There’s just one challenge remaining: Your outfit. You don’t get a second chance to make a great first impression, and in order to ace your first date, you’ll need to step it up in the wardrobe department.

“In our parents’ time, guys had to be dressed to the nines for a date with a full suit, or at least a collared shirt, but these days, things tend to be a lot more casual,” New York-based men’s stylist Seppe Tirabassi tells Men’s Journal. “Still, you’ll want to elevate your look for nighttime while staying true to your own sense of style.”

For Tirabassi, date night—regardless of whether it’s a first or fourth date—is a solid excuse to treat yourself to a new outfit.

“To get the vibe right, seek out some pieces that will live as Friday night staples,” he adds. “Keep it simple and unfussy, but sophisticated enough to show that you’re making a greater effort than on any other day of the week.”

One surefire way to step up your date night look? Get the right pair of shoes, like Cole Haan’s 4.ZERØGRAND Stitchlite™ Oxford. The knit upper is super breathable and temperature-regulating, which will keep your feet cool and comfortable in case there’s an onset of the first-date jitters. Better yet, the responsive foam sole cushioning will help prevent achy feet—no matter how long the night lasts.

Innovative comforts like these are typically reserved for performance shoes, but Cole Haan’s ​​4.ZERØGRAND Stitchlite™ Oxfords are in a wholly different category than your average kicks.

“The riff on the classic wingtip pattern elevates the shoe into formal territory,” Tirabassi says, “but everything else about it is refreshingly casual. Even though there’s a white sole, which you usually see on sneakers, the dark navy pair is very appropriate to wear in the evening.”

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With a sharp pair of shoes anchoring your look, the next step is to build an outfit around them. Since warmer weather is on the horizon, Tirabassi suggests pairing your kicks with a pair of Cole Haan’s Terry No-Show Socks. They’ll create a breezier look, and with their cushioned sole and added arch support, they’re designed to keep your feet feeling good, too.

Next up: denim. But don’t reach for your everyday jeans that are worn-down in all the wrong places; instead, go for an edgier look with selvedge denim.

“It’s all in the details,” says Tirabassi. “A nice pair of selvedge denim jeans, like Todd Snyder’s Slim-Fit Selvedge Jean, comes across more high-quality because they’re crafted in thicker fabric with a cool finished edge. They also age really well.”

Before you leave the house, he recommends cuffing your jeans at the ankle by an inch or two to reveal the contrasting stitch details—and to show off your shoes.

But what to wear on top? Tirabassi suggests a simple, unwrinkled white T-shirt, which will make an ideal base for layering. He likes the crewneck cotton-jersey tee from OTD, a new streetwear brand from menswear designer John Varvatos. On top of the shirt, throw on a light sweater in a neutral color like gray or black.

“Depending on where you’re located, it could still get chilly at night, so adding an easy layer is a good idea,” he says, “A lightweight Naadam cashmere sweater looks clean and sophisticated. I like when there’s a bit of white from the T-shirt collar peeking out.”

Finally, cap off your date night duds with a rugged-yet-refined suede trucker jacket, like Banana Republic’s trucker jacket in heritage suede, and a slick watch with a leather strap (Tirabassi loves Shinola’s new Runwell 47mm).

“Go for brown leather here, which will point back to the heel patches on the ​​4.ZERØGRAND Stitchlite™ Oxford shoes,” he says. “It’s all about having an eye for detail—that’s how you’ll ace your first date.”

[Cole Haan 4.ZERØGRAND Stitchlite™ Oxford: $210; colehaan.com]

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