Step Out in Style With Cole Haan’s American Classics Penny Loafer

Cole Haan American Classics Penny Loafers surrounded by brown pants, a white shirt, a brown sock, and a brown leather belt on a beige background
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This article was produced in partnership with Cole Haan.

Among all the occasions in a guy’s packed social calendar, a night out on the town demands an outfit with a touch of stylish flair. To get the right look, you need to nod to the classics while also looking fresh and modern; you want to switch things up ever so slightly from the ordinary without overdoing it.

According to Cassandra Sethi, an NYC-based stylist and image consultant at Next Level Wardrobe, dressing for a date or ringing in a special occasion with the guys—with cocktails or mocktails in hand, of course—is a great way to try out sharp pieces rooted in timeless style.

Footwear is the foundation of your outfit, and the right shoes can make or break a look. That’s especially true when dressing for a night out that could lean a bit more casual or just a touch more formal (an evening at a rooftop bar or a classy steakhouse, for instance). So where to start? You can’t go wrong with a new take on a tried-and-true footwear favorite.

Consider the penny loafer: It’s an iconic style with deep roots in men’s fashion. It was first worn on school campuses, and it has long been top choice for stylish men the world over. The ideal penny loafer is classic but comfortable, delivering modern performance and all-around good looks—precisely like the Cole Haan American Classics Penny Loafer.

Rich dark brown leather and Cole Haan’s signature comfort deliver both spring in your step and effortless style, and they’ll provide a nice contrast to the other key components of your outfit. These shoes feature a durable storm bead welt and a grippy ruffed outsole tread, and they include a heavy gauge stitch penny keeper (essential for any true penny loafer). In addition to the classic construction, they’re comfy, too: The shoes are made with a pillowy EVA footbed, and every component is designed for low weight, so they won’t feel clunky on your feet.

That comfort-meets-classic ethos is exactly what you want for a night out. The Penny Loafer will help you stand out subtly, and it can easily transition from one evening stop to the next. (That steakhouse dinner might spill over into a nightcap at a trendy new speakeasy.)

With your feet squared away, you’ll need to craft the rest of your outfit. One thing to keep in mind: A night out is the perfect opportunity to switch things up from your daytime looks.

A textured, woven short-sleeve shirt is a smart, sharp way to dress your top half, and it’s a welcome departure from a traditional polo or short-sleeve button-down in a solid color (although both of those options would work, too).

Sethi says the woven shirt is one “you can wear with complementary-colored trousers” or with tones like navy, grey or black. But she especially recommends some light brown stretch wool tailored pants for a look that toes the line between casual and formal. They’re the perfect pick for the man who’s into versatile, multi-faceted style.

“The earth tone wool trousers are perfect for a formal touch,” she tells Men’s Journal. “They’ll look cool for a night out and keep their shape.”

Better yet, you can reach for these crisply cut stretch wool trousers when dressing for other occasions, too.

“These you can wear throughout the year as well with a switch of top and footwear,” Sethi says.

The shirt and pants make a great team when paired with Cole Haan’s American Classics Penny Loafer: You’ll stay cool on top while nodding to the ever-shifting seasons on your lower half. In other words, it’s the right blend of casual and crisp.

This is one look in particular that’s “perfect for those hot summer days,” Sethi says, but it can be layered with a sport coat if the evening turns cool or if things get more formal.

Finally, accessories are all-important, especially when dressing to impress. Sethi recommends styling your penny loafers with an eye-catching pair of socks in a color that also plays off your stretch wool trousers—like the Cole Haan Tonal Argyle Crew Socks.

The pattern on these socks nods to a sense of fun and style without overdoing it. You can also team your penny loafers and argyle socks with Cole Haan’s Harrison Grand 32mm Belt to really knock this outfit out of the park.

Think of it like going four-for-four with handsome, refined shades of brown in your footwear, your sock choice, your belt, and your light brown pants. With Cole Haan’s American Classics Penny Loafer anchoring this outfit, you’ll be ready for wherever your night takes you.

[Cole Haan American Classics Penny Loafer in Deep Burgundy/Black, $160; colehaan.com]

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