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Oversized Pants are In. Here’s How to Wear Them Best (and Which To Buy)

Oversized Pants are In. Here’s How to Wear Them Best (and Which To Buy)

If you haven’t heard, big pants are in. Relaxed-fit, oversized–it’s all fair game. After nearly two decades, the skinny jeans spell is nearly broken in the collective consciousness, and menswear brands everywhere are going for a roomier look that harkens back to the 1990s.

It can be argued that the slimmed-down look has been going out of style for some time now, but it was J. Crew’s recent release of its giant-fit chino that really put the nail in the proverbial coffin. With the recent appointment of NOAH founder Brendon Babenzien as creative director of J. Crew, the brand has been willing to take risks while looking to the brand’s archives for inspiration.

J. Crew is far from the only one. Streetwear and menswear enthusiasts alike are embracing the baggy, the saggy, and the loose-fitting trousers, and I’m here to ride this trend for a while.

How to Style Oversized Pants

The main thing guys worry about when adopting a looser fit is that the proportions will be out of whack. And if your clothing usually leans towards a trimmer fit, then that might just be a real problem to consider. But if you’re like most guys and are buying off-the-rack and not too interested in tailoring, then it won’t be too hard to incorporate a few pairs of loose-fitting chinos into your rotation.

There are two main templates for wearing a looser-fit trouser. You can either go with that 90s prep look or with a casual, everyday approach. Either way, an oversized pant can give you a blank canvas to create a classic look.

If you’re going the 90s prep route, then I recommend looking at old movies (particularly anything with Hugh Grant) or at vintage-inspired Instagram accounts, such as @oldralphlaurenads. You’ll want to focus on oxford shirts (tucked in, of course), loafers or chunkier sneakers, and a clean color palette.

Alternatively, it’s easy to incorporate oversized pants into your existing wardrobe for a casual look that’s not exactly dressy, but still appears like there was some thought behind your outfit for the day. As long as the bottom of your shirt or sweater is around the same width as the pants at the upper thigh, the proportions of the outfit won’t appear off. This works with hoodies, sweaters, and jackets. You’ll want to avoid slim-fitting shirts and tees as they disrupt the natural line of the more relaxed fit. Otherwise, you’re golden.

Top Picks

J. Crew Giant Fit Chino

J. Crew Giant Fit Chino

It’s hard to not see this chino as a defining moment for the new direction of J. Crew, which is inspired by the past. With an array of classic, neutral colors to choose from, you’ll be rocking your inner Jerry Seinfeld or Chandler Bing in no time. What I particularly like about this fit is the extra-long rise on the crotch and waist, giving a longer overall proportion that lengthens the silhouette to combat against the added fabric.

Buy Now $98+

Polo Ralph Lauren Whitman Relaxed Fit Pleated Chinos

Polo Ralph Lauren Whitman Relaxed Fit Pleated Chinos

Ralph Lauren drew the blueprint for casual prep and it’s good to see their Whitman chino is keeping that legacy alive. The casual drape and khaki color make this a pant that can be worn with nearly anything already in your wardrobe. The pleating and ticket pocket in the front add just the right amount of detail to this trouser to set it apart from other similar styles.

Buy Now $168

COS relaxed fit tapered chino

COS Relaxed Fit Tapered Chino

COS has produced some of the best basics around and the brand’s tapered chino is no different. The pleating on this one is subtle, so it doesn’t add bulk, but it does give it the tiniest bit of detailing that a flat-front pant doesn’t achieve. These pants only offer a standard inseam, so short kings may need to get their tailor on speed dial if they’re ordering.

Buy Now $120

ARKET wide leg cotton chino

ARKET Wide Leg Cotton Chino

ARKET”s wide leg chino have an extra amount of room in their leg that runs straight from the thigh to the ankle opening. While others may taper, this pair from ARKET keeps the lines clean and this added room makes for a comfortable all-day wear.

Buy Now $119

cast lane weekender trouser

Cast & Lane Weekender Trouser

Just by looking at the brand and styling, it’s easy to see that Cast & Lane is inspired by the bygone, Oxford-adjacent style of 80s and 90s London. With its 9.25” high rise waist and generous cut throughout the leg, this is a pant that’s daring, bold, and impossibly cool.

Buy Now $126

Dockers Made in the USA Relaxed Tapered Fit Chino

Dockers Made in the USA Relaxed Tapered Fit Chino

Dockers Made in the USA collection is a higher tier alternative for the brand and the quality is evident with these pants. Made from a no-stretch khaki that keeps its shape with extended wear, these chinos add a bit of a workwear edge to a traditionally dressy look.

Buy Now $140