For Men’s Fall Fashion, It’s All About The Pants

With colder weather fast approaching and fall officially here, many of us are looking for ways to revamp our wardrobe. While a chunky sweater, a few pairs of cords and maybe some oxfords will get you through the season, that look can get a little stale. If you’re looking to level up your wardrobe, it’s time to pull on a pair of oversized pants.

On the runway and off, roomy pants have been having a moment. Whether you’re going a Row-inspired drape or a more high-waisted fit like Tom Ripley, oversized pants don’t have to mean baggy; they can be the ticket from turning your wardrobe from the dull everyday office fit into something a bit more interesting.

Big Pants’ Big Moment

Many guys who grew up in the early aughts may have an initial aversion to anything baggier than a bootcut. And to those Gen X’ers, don’t be mistaken in thinking larger pants are the baggy skater type. Instead, the swing toward an oversized fit is a result of the high fashion distillation into the ready-to-wear market due to a confluence of cultural inspiration, more lax rules surrounding gender in fashion and even Covid-19.

The first—and arguably the biggest—inspiration for this shift to an oversized fit is that fashion is cyclical. Larger fits have slowly crept back into our cultural consciousness through the cross-pollination of Instagram accounts dedicated to vintage fashion ads, prestige television highlighting perfectly draped outfits and ‘90s nostalgia. By capitalizing on this inspiration, brands like J. Crew have been able to look into their archives to recreate contemporary pieces with a vintage flair, like its Giant Fit chinos. Releases like this have brought renewed attention to the oversized pant while giving men new ways to style their wardrobe with one simple addition to their closet.

It hasn’t been just J. Crew that has put out some great oversized pants lately. Brands like The Row and Lemaire show that this trend toward the voluminous is hitting the luxury side of the industry, too. But it’s also showing a narrowing of the gendered differences between menswear and womenswear. In both The Row’s and Lemaire’s case, there is not much distinction between the options for men and women, proving that the shift in freedom of expression has also influenced a more neutral silhouette that’s appealing for any body—or anybody.

Finally, oversized garments may have had a practical reason for becoming en vogue as well. According to the National Institute of Health, nearly 40% of Americans gained weight during the COVID-19 pandemic. A comfortable means of adapting to one’s new body is to gravitate toward less form-fitting garments. While inspiration and blurred gender lines may have played a role in the popularity of oversized pants, maybe adapting to our new bodies helped expedite this adoption.

Where To Find Inspiration

Fashion and media are constantly in dialogue with one another, and there is an array of touchpoints from which to draw style inspiration from if you’re curious about oversized pants. For loose-fit tailoring, ‘80s movies strike the perfect balance between structure and relaxed style. American Gigolo is a great source of inspiration. In fact, Richard Gere’s entire wardrobe for the film was supplied by Armani, so looking at archival pieces from this time period could work to inspire your fall outfits of today.

For more contemporary examples, Netflix’s Ripley did a supreme job of capturing 1950s Italian style, often mixing proportions in various linens and knit shirts. And unsurprising to those who saw the film, Cate Blanchett’s titular character in Tár has an incredible wardrobe that is unique, masculine and playful with proportions.

Alternatively, Instagram has become a resource for many who wish to find inspiration from vintage catalogues, like those scanned in @vintagemenswearmagazines and @oldralphlaurenads. These accounts often feature editorials from when oversized garments were still in style, giving you an archive of inspiration to scroll through.

Styling Tips For Fall

When it comes to finding the perfect way to pair your oversized pants with your current wardrobe, you need to think about proportions. Because of the extra room throughout the leg and seat of the pants, you can either battle against the wide leg, or lean into it with fuller proportions all over.

For shorter guys, consider pairing your pants with a shirt that ends right at the hips. Often, oversized pants have a longer rise and sit higher at the waist. By accentuating this contrast in proportions, you can create the illusion of longer legs while also adding a bit of an Old Hollywood flair to your look à la Gene Kelly.

Another option would be to lean into the oversized look with your top and bottom. By adding extra fabric to your shirt or jacket, you can create an eye-catching outfit without a lot of effort. If the shirt isn’t structured to be oversized, then try to go a size larger and visit a tailor to get the proportions just right. Alternatively, J. Crew’s Giant Fit pants have a matching Giant Fit oxford, making it easy to mix and match an outfit that will undoubtedly make a statement.

You can take this a step further and lean into the loose tailoring that’s popular on the runway today (look at Zegna’s latest runway show for an example). Pairing your oversized pants with a matching blazer gives an overall aesthetic that’s reminiscent of 1980s Armani. A great option for an unstructured suit would be anything from Uniqlo’s AirSense line. If you’re looking for something a bit elevated, I’d highly recommend this relaxed suit from Todd Snyder.