The Most Flattering Clothes for Men, According to Real-life Men

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It’s all about the cut.

It all started with a simple pair of pants. We posted about this suspiciously flattering pair a little while back and the response was so enthusiastic, it got us thinking: Why not sniff out the most flattering things across a bevy of categories, from the most skin-enhancing light bulb to the brightening eye drops to the shapewear designed for all sizes? Welcome to Flattering Week on the Strategist.

Different men have different needs. Some of us are self-conscious about our chests. Others want their legs to look longer. Over time, most of us have learned some tricks for showcasing our assets and hiding our flaws. To learn these secrets, we went straight to the source, talking to 11 guys about the most flattering piece in their wardrobe, from the slimming chinos to the pec-embracing Henley.

Face-framing Shirt

“I only very rarely find myself having to wear collared dress shirts, but my favorite not-quite dress shirt to wear is the band-collar shirt, which has the dressed-up vibe of a typical button-down without being quite as stuffy or square. This one’s got the cool cut (slim around the torso and the perfect length for wearing tucked or untucked), but my favorite thing about it is the band collar, which actually frames your face nicely if you leave the top button unbuttoned. It’s that bit of oomph that a regular oxford doesn’t give you.” — Jason Chen, senior editor, Strategist

Buy
Bonobos Band Collar Shirt $98, Spring

Most Forgiving Shorts

“These cotton shorts from Saturdays are essentially just cut-off sweatpants — which is a perk if, like some of us, you’re rolling into summer a few stomach flus above your goal weight. The waistband is forgiving, but they’re trim and short enough that they don’t seem too slouchy to wear out and about. They come in a couple colors, but I like the indigo, since it’s dark enough that from a distance, no one can tell exactly what they’re made of.” — Ben Reininga, editor-in-chief, Vocativ

Buy
Saturdays Austin Sweat Short $120, Saturdays

Bicep-Hugging Henley

Henleys are a really tough shirt to wear well, but it’s not necessarily your body’s fault. In my experience, materials can be off, the fit can be a little drastically skinny — or, more often than not, they can just hug you in all the wrong areas. But I bought this Henley a few years ago, and never went anywhere else. The length is just right — they’re light enough to wear solo in the summer, but good for layering when it’s chilly, and they make you look slightly more in shape than you are in the arms and shoulders and pecs. Always the first shirt I wear out of the wash.” — John Jannuzzi, U.S. editor, Twitter Moments

Buy
Save Khaki Cotton Blend Henley $90, Mr Porter

Sexiest Underwear

“A decade ago, back when American Apparel wasn’t bankrupt, it seemed every man owned that company’s Technicolor briefs, but then I started to notice that all guys (muscle queens in Fire Island, schlubby tech bros in the gym locker room) had switched to Calvin Klein’s cotton stretch briefs. I bought them myself and understand now: The 5 percent elastane keeps your junk in place without bunching between your legs, and the gracefully curved leg holes are the platonic ideal of what briefs should look like: classic, not porny. Black is, of course, the sexiest and most flattering choice here.” — Kurt Soller, features editor, Bon Appétit

Buy
Calvin Klein Cotton Stretch Briefs From $14 for three, Amazon

Best-Cut Sweatpants

“These Save sweatpants are the first pair I’ve loved since I had to retire the striped Adidas sweatpants I got in high school. They’re cut in a way that’s neither too fitted (like old high-school gym sweatpants) nor too baggy, which allows them to work even with sweaters and button-downs (versus tees and sweatshirts) when you’re walking the dog or going to the bodega.” — Ian Klein, senior director, Corigin Real Estate

Buy
Save Khaki Sweatpants $95, Mr Porter

Best-Fitting Swim Trunks

“Finding great swim trunks requires a multipronged strategy. There’s the length, which should hit around mid-thigh on a guy — optimal for tanning without being too revealing — and the cut, a bit fitted but not too tight, lest it makes you look bigger than you are (or like a kid). And a netted lining inside — mandatory, I say — which should be a bit looser than briefs, so it holds everything in place. This is the best option I’ve found. Perfect cut, with a drawstring waist that stretches no matter what my summer bod looks like.” — Tony Nikolla, vice-president, Edelman

Buy
Gant Classic Swim Shorts $67, Amazon

Slimming Chinos

“Finding the perfect chino has been a lifelong pursuit: Over the past decades, I have worn styles by American Eagle, Banana Republic, Dockers, and Trovata. It was life-changing to discover Acne trousers, though. From the hips down, my body could be described as “reverse hourglass” — narrow at the hip, wider at the thigh, then narrower again to the feet — and the tapered leg sort of perfectly follows my anatomy, giving my lower half a clean, linear, and somewhat longer appearance. The style’s waist is higher, which not only keeps my stomach from spilling over the pants’ edge but also allows for seamless layering (shirts are tucked close to my body, so throwing a sweater over one never looks bulky at the hip).“ — Anthony Rotunno, features director, DuJour

Buy
Acne Studios Alfred Slim-fit Chino Trousers $260, Matches Fashion

Tailored Denim Shirt

“I love a denim shirt because I can wear it tucked or untucked, buttoned or not. I’ve tried many in my day, but the best one is Uniqlo’s because it’s actually slim-fit, and unlike other denim shirts, doesn’t swim around you at the waist. It means I can button it up and tuck it in without billowing over my pants.” — T.T. Tu, social-media manager, Cole Haan

Buy
Uniqlo Slim Fit Denim Shirt $30, Uniqlo

Chest-Enhancing T-shirt

“When I got my first one I was like, Damn, my chest looks good! I think the cut of the T-shirt itself is just very flattering — it’s not overly baggy at the bottom like some Uniqlo T-shirts I’ve bought, and the neck area is cut so it’s not super open to expose a lot of chest. Instead, it sits just above the collarbone, which to me is sexy without being uncomfortable.” — Eddie Camacho, art director, Havas

Buy
COS Cotton Blend Round-Neck T-shirt $45, Mr Porter

Expensive-Looking Hoodie

“Even though I love hoodies, I’ve always been a little underwhelmed by what’s available out there — until I discovered (yes, really) Gap’s. They fit perfectly (not too big around where the pocket is, which is the true test); the hood is just the right size (even when you’re wearing a beanie on cold days); and it’s so soft that it almost feels like cashmere — but I only spent $30 on it. Literally every time I wear it, someone asks me what brand it is, like they’re expecting something much more expensive.“ — John Wogan, writer

Buy
Gap Fleece Pullover Hoodie $30, Gap

Thigh-Skimming and Butt-Hugging Jeans

“I’m skinny without being waifish, which is why I love J Brand’s Tyler-fit jeans. They’re slim without suffocating my thighs (and make the ass I’ve earned from power vinyasa look better, too).” — Andrew Richdale, deputy editor, Saveur

Buy
J Brand Tyler Slim Jeans $228, Amazon

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The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best women’s jeans, rolling luggage, pillows for side sleepers, ultra-flattering pants, and bath towels. We update links when possible, but note that deals can expire and all prices are subject to change.

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The Most Flattering Clothes for Men, According to Real Men