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The Best Warm-Weather Clothes for Cuddly Guys, According to Stylists

Photo: Courtesy of FOX

I love and look forward to warmer weather as much as anyone. But even before gyms locked their doors and we were told to stay home surrounded by food we’d stockpiled, as a guy who is carrying about 20 pounds more than he’d like, I was starting to worry about what to wear now that the weather no longer calls for layers upon layers. In discussing my dilemma with an employee at prep mecca J. Press (pre–social distancing), he told me one thing I should invest in is a “sack jacket” — a traditional men’s blazer cut for heavier guys, with more breathing room in the waist and shoulders to prevent the wearer from feeling like a sausage in a casing. His immediate answer made me wonder if there are other slimming garments that guys like myself can get to look and feel our best.

The answer, according to the five cool people I spoke to — who include stylists and menswear-store owners — is yes, there are other garments out there that are better suited for camouflaging extra pounds. Read on for the button-downs, polos, T-shirts, shorts, and pants that they recommend for cuddly guys — essentially, anyone who has gone up a couple notches in their belt since buying it — which include a few of my own favorite flattering items, too. And one piece of shopping advice shared by all of the people I talked to: When choosing a size, pick the one that actually fits. As George Brescia, a stylist and the author of Change Your Clothes, Change Your Life, puts it, “When we wear clothes that are too large and oversized, the wearer becomes as big as the item.” Speaking of sizes, all the garments on this list go up to a size XL, with many offering more sizes (we’ve noted which ones have a wider range).

Button-down shirts

All five of our cool people told us about the importance of creating vertical lines down your body, as they “elongate your look, making you appear taller and leaner,” explains Donnell Baldwin, a former style director for Mr Porter. The best garment for creating long, vertical lines, according to them, is a button-down shirt because, as Brescia notes, “the buttons going down create the line,” while the collar helps to create a flattering shape. “Collars frame your neck and bring back some angles to your look,” adds Peter Nguyen, a personal stylist. Two of our cool guys pointed us to this specific button-down from Bonobos (which goes up to a XXL) as a flattering style, not only for its buttons, but also it’s vertical stripes. “Vertical stripes on an item are your friend, too” says Baldwin. “Plus, they’re timeless.”

An even more affordable option with vertical stripes is this blue-and-white Gap button-down that goes up to a XXXL, which Baldwin loves because it “gives off a nautical, easy, free-flowing style,” especially as it’s designed to be worn untucked. He owns one himself, telling us that it has lasted him multiple seasons. He adds that the shirt’s combination of poplin (a lightweight cotton) and stretch material makes it easy to move in and breathable.

If stripes aren’t your thing, a simple, solid button-down can still flatter. For warmer weather, Nguyen says this J.Crew one made of chambray (which has the look of denim, but is lighter) is a “a solid option.” (Consider it the lightweight equivalent of the J.Crew denim shirt beloved by both Strategist editors and columnist Chris Black.)

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This under-$20 button-down that Baldwin recommends also has slimming vertical stripes, is designed to be worn untucked, and has short sleeves, making it ideal for hotter days. Plus, it sizes up to XXL.

Photo: Retailer

On the other end of the pattern spectrum, Nguyen says that a button-down with a “busy, all-over print is a great way to camouflage your belly.” Baldwin told us he also likes an all-over print, as it can “distract the eye, making you appear slimmer.” He directed us to this short-sleeve button-down with a sort of neon, New York City–at–night print, but says the most important thing is to find a print that works for you and “rock it with reckless abandon.”

For another flattering all-over print, Nguyen pointed to this short-sleeve button-down with a bright bull’s-eye pattern from Todd Snyder, which runs up to XXL and is designed to sit untucked just below the waistline.

Photo: Retailer

If you’re looking for something slightly more casual that still has those flattering elements, namely buttons and a collar, Sean Crowley, the owner of Crowley Vintage, suggests this Alex Mill “popover” shirt that’s kind of polo shirt–button-down hybrid. “Popovers are about as old fashioned as it gets,” he explains, “but they’ve had a revival in the last few years. The fit is generally a little looser than a regular button-up shirt, and they look great tucked or untucked.” It runs up to a size XXL.

Polos and T-shirts