17 Objectively Correct Reasons to Go All-In on Dress Pants This Winter (2024)

Uniqlo's satisfyingly wide dress pants have that respectable dress pant energy with an inner monologue of your favorite sweatpants thanks to the discreet elastic waist and hidden drawstring. They come in a handful of classic colors and cost just fifty bones, so you can stand to grab more than one pair.

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.

The only shadow we want to live in is these shadow plaid trousers.

Good to know: antique wallpaper makes for a sick pair of pants.

POV: your office is a skate park.

Lean into the old man style. Double pleats, a sweater vest, and some good walking shoes should earn you some respect from your elders.

You can leave your reversible belt at home, these pants come with their own.

J.Crew's Kenmare suit is joyously relaxed and unstuffy, which means you can feel good about wearing the trousers totally separately.

Lounge-y dress pants or formal sweatpants—you decide.

One of menswear's beloved indie labels has built its reputation on irreverent office wear with a slouchy sensibility and these mini houndstooth trousers achieve their full potential with a baggy button-up and a pair of Asics.

A lot of brands aspire toward a utopian world of casual tailoring, but rarely do they achieve that. Stòffa does. These dress pants feature a luxurious cotton twill fabric that's been lightly brushed for a peachy hand, a relaxed silhouette with a classic single pleat front, and elegant adjustable tabs at the waist. They're the kind of pants you'd expect to see on an impossibly swaggy Italian grandpa, with a slouchy polo and woven leather sandals.

It's difficult to design a pair of elastic waist trousers look like the actually belong at a black tie event, but if you're the design duo behind The Row, it's a cinch.

Thome Browne changed the game with his legacy-defining shrunken grey suits which have become a source of endless iteration. These super smooth wool trousers feature a slim silhouette with Browne's telltale high-water length and a cheeky rear button strap.

If a bomber jacket had its fabric grafted onto a pair of tuxedo pants, it would look like this.

Britain's madcap color theorist knows when to tone down his palette, too. That's not to say Paul Smith's ultra-sharp trousers are boring—the opposite, in fact. All that means is that the subtle checked pattern won't elicit eyeballs at the office, but will look right at home when you ditch the dress shirt and loafers for a silky button-up and kicky boots.

Most dress pants are made of woven fabric, but Todd Snyder somehow managed to make a knit fabric that has all the natural stretch and comfort of your favorite T-shirt, but the look of an actual dress pant. Who said suits were uncomfortable?

When the event you're attending calls for either black tie or—god forbid—'dress to impress', a pair of velvet dress pants will pass muster in both situations. These sultry velvet pants from Banana Republic have a great tailored silhouette that's trim but not tight and will look ace with a pair of patent loafers or even with just a plain white tee and Sambas, treated like a swanky pair of track pants.