18 Wildly Stylish Men’s Dress Pants to Wear Anywhere But the Office
Say it with us, folks: men’s dress pants aren’t just for dressy occasions. It’s time to stop associating tailored trousers solely with job interviews, important meetings, and weddings, and start wearing ‘em wherever you goddamn please. Right now, there’s nothing more exhilarating than stepping out into the world feeling wholly put together, and there’s no easier way to do that than pulling on a pair of perfect-fitting dress pants.
How do you pull off dress pants in a casual setting without feeling too stuffy, you ask? First off: treat ‘em the way you would your jeans. That means skipping the starchy dress shirt and tie and reaching for your easiest, breeziest tees, hoodies, tanks, and camp shirts instead. Try them with sneakers, loafers, mules, or boots. Go as wild or as minimalist with the rest of your fit as you like, and then let the rakish elegance of the trousers elevate the whole operation. Secondly, play around with the silhouette. Trim and tailored will always look great, but as with so much of menswear, drapey and relaxed is king right now. If your dress pants are slouchy and billowy enough to look right at home at a skate park, absolutely no one will wonder if you accidentally wore your work clothes to the bar.
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Convinced yet? Good. A whole world of proper trousers awaits you, and we’ve selected a baker’s dozen of the finest men’s dress pants to get you started. Your legs can thank us later.
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Uniqlo Smart 2-Way stretch jersey ankle-length pants
If you don’t know where to start, start here. They’ve got the drape of a proper dress pant but the buttery feel of your favorite sweats. Whether it’s the silkiest of shirts or the crunchiest denim jacket, these pants will handle it all with grace.
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Berle touch finish pleated plaid classic fit stretch trousers
Lean into the old man style. Double pleats, a sweater vest, and some good walking shoes should earn you some respect from your elders.
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Todd Snyder glen check Sutton suit pant
Check, please!
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Needles tile-jacquard trousers
[Beeges plays in the distance, from the nearest nightclub]
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Drake’s chalk stripe flat front trouser
Subvert the chalkstripe and its ties to business deals by wearing these with some thrashed sneakers and a vintage tee.
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COS relaxed-fit wide-leg twill chinos
Delightfully rumpled and these are ready for a day off (whenever that is). Pressed and starched, and they’re sharper than a tack and primed for a day at the office.
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Polo Ralph Lauren slim tapered fit Prepster pant
The chimeric category of the elasticated dress pant may sound strange in theory. In practice, it works like a charm. Just make sure to leave your shirt untucked.
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Stòffa pleated brushed cotton-twill trousers
With just the right hem, you can go wild with textures and pair your dress pants with some chunky socks and Birkenstocks.
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Noah single-pleat suit pant
Don’t be afraid to mix patterns, either. Try a pair of subtle plaid pants with a bold camp collar shirt and some crispy white sneakers.
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Dockers relaxed fit comfort pants
The double pleats, the beautiful drape, the sweet price point—these are the dress pants to get when you’re trying to score as many style points for the least amount of money.
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Gucci polka dot velvet pant
Slip into some swanky loafers (or even some heels) and your finest pearls, because pants like these are meant to be SEEN.
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Acne Studios wide-leg organic cotton-twill trousers
The sliiiiight flair is juuuuust right.
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Thom Browne paneled trousers
Thom Browne (AKA King of the cropped look) knows that, come fall, you’ll want to show off your killer boots.
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Tanner Fletcher “Clarence” trousers
Grannie’s silk curtains look positively drippy as pants.
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S.S. Daley pleated pinstriped cotton trousers
You know the saying—go big or go home.
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Lemaire belted two-pleat trousers
There’s that rule that says you should match your belt to your shoes. But nobody ever said anything about matching your belt to your pants.
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Barena Delfo straight-leg wool-blend flannel trousers
When chinos are just a tad too cazh, opt for these khaki-colored joints for a similar effect that can still be worn with white sneakers for the daytime or white derbys for the dance floor.
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Isabel Marant “Reiko” trousers
Don your coziest oversized sweater and you’ve got the dressy equivalent of your Sunday sweatsuit.
(LEFT) BLUEBERRY PECAN BREAD, (RIGHT) SOUR CREAM BLUEBERRY BUNDT CAKE. EXCERPTED FROM BLUEBERRY LOVE (C) BY CYNTHIA GRAUBART, PHOTOGRAPHY…
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