The Strategist’s Menswear Hall of Fame
The clothes that men from all walks of life recommend to everyone they know.
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Are your pants wide or skinny? Mine are wide, which aligns with what most menswear experts say is currently cool. Yet the top-selling men’s pants on Amazon are still as slim and stretchy as they were at the end of Barack Obama’s presidency. In real terms, expert opinions on what to wear have never mattered less, which is why I’m taking a different approach to this year’s Menswear Hall of Fame. Rather than building a cohesive wardrobe for a hypothetical reader, I wanted to present a wide-angle snapshot of the clothes that men from all walks of life like enough to recommend to everyone they know.
Whether you prefer boxers to briefs or jeans to chinos, who wouldn’t want to hear about the women’s sweatpants that Rob Thomas is willing to wear outside the house (recommended by his zoomer son), the workwear jacket that keeps a North Dakotan veterinarian from freezing during mid-winter barn visits, and the half-priced Paraboot dupes our restaurant critic happily wore every day for over a year.
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Made of hefty cotton jersey that drapes and ages nicely in any color.
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A flattering T-shirt for shorter guys, beloved by ‘Vogue’ editors and celebrities alike.
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Soft from the start and only gets better with age.
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Gildan’s tees are substantial (but not too thick), and, most important, they’re very cheap.
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The best polo under $50, made of breathable 100 percent cotton piqué.
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Made from luxuriously soft cotton jersey in a wide range of colors.
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The design remains mostly unchanged, nearly a century in.
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Available in five fits for different tastes and body types — and relatively affordable.
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A timeless dress shirt, with tailoring included in the price.
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Buy-it-for-life buttondown with all the right details.
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Pedro Pascal’s zombie-fighting flannel.
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Easy to layer and not scratchy with a fitted yet relaxed drape, it comes in over 36 colors.
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A well-made slinky sweater made from the softest cotton.
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Noah founder and former J.Crew creative director Brendon Babenzian runs in his.
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Cozy, durable, and comes in over two dozen colors.
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Made in L.A. from the coziest heavyweight cotton.
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A heavyweight sweatshirt with a soft interior and sturdy face.
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Straight-leg, huge size range (including big, tall, and loose styles), and under $100.
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The wider leg and roomier thigh provide a more modern fit.
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Made the right way, with a slightly relaxed straight fit and copper hardware.
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The pleated jeans one stylish couple share.
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The not-too-wide barrel-leg pants David Lebovitz wears every day.
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Unfussy wide trousers to dress up or down.
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You can trust Scandinavians to make the best cold-weather clothes.
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The most nicely made chinos for under $100. They work for semi-formal settings, too.
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The original pull-on pants, updated with a more relaxed fit.
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A classic pair of fleecy sweatpants.
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Rob Thomas’s favorite sweatpants, recommended by his zoomer son.
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Roomy, not baggy. Modest, not long.
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Crowd-favorite trunks that look great on land and perform well in water.
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The most versatile, go-anywhere gym shorts.
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A more modest Speedo made from the nicest fabric.
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Baggies-esque but actually made for swimming, and they look great on land, too.
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Aaron Levine wore these as his only shorts for a weeklong beach vacation.
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More durable than cheaper rain jackets, with performance that rivals the best.
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Statusy rain jacket that works well on trails and looks great in the city.
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Warm, but not too warm. Perfect for travel.
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Plastic-free fleece, made from Italian-milled recycled wool and cotton-bound edges.
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A versatile jacket that works as outerwear or a layer.
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A great price on a 100 percent wool coat.
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You can trust the Brits to make good rain protection.
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The once and forever New Yorker’s puffer.
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Warm enough for working outdoors in mid-winter North Dakota.
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The best starter suit, made famous by Mayor Mamdani.
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A buy-it-for-life suit, made in Italy from high-twist fabric with full canvas construction.
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The double-breasted blazer favored by downtown creatives.
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Larry David would approve of this not-too-soft robe’s absorbency and texture.
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Warm, breathable, stink resistant, and last through many years of daily wear.
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A five-pack that you’ll come back to again and again.
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I struggle to distinguish my ten-year-old pair from the newer ones.
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Giftable boxers sewn from the highest quality cotton poplin.
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Durable and affordable socks that come in 50 colors.
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A softer wool blend for better moisture control.
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Indestructible wool socks, backed by a lifetime warranty.
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Gorp-y recovery shoes for climbers … and walking your kid to school.
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Affordable Paraboot dupes, still assembled in France.
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Soft-soled Turkish leather slippers that look great with everything.
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The next big thing after Salomons, recently spotted on Harry Styles.
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An unpretentious prep staple that’s worth the break-in period.
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Repairable Chelsea boots that work with jeans and suits.
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A pickleball shoe that doesn’t take itself too seriously.
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Supportive hiking sandals that work great in water.
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Sock-friendly sandals designed in Japan, discovered in Basque country.
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A starter chain made from real silver.
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A not-too-western belt to add some sparkle to any outfit.
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If you get only one tie, make it this one. It goes with everything.
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Cool-dad sunglasses that stay on your face, no matter what.
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The cheap shades beloved by both Duplass brothers.
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Fingers stay warmer when they’re together.
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Show your support for ‘New York,’ now in championship-winning colors.
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One hundred percent wool watch cap at a polyester price.
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It took over NYC in 2018 and never left.
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Worn by multiple 2026 Winter Olympic medalists.
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Sturdy saddle leather, stitched with extra-thick thread.
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Cut and folded from a continuous piece of leather. Comes in many colors.
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A sturdy minimalist wallet, recommended by Chris Black.
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Omega looks at a Timex price, inspired by archival designs.
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A favorite diver among in-the-know collectors, from a respected Japanese watchmaker.
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Looks and works great for commuters and hikers alike.
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Art-world-approved backpack that folds into its own internal pocket.
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The ultimate laptop backpack, beloved by our tech writer and Kate Berlant alike.
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A cheap tote that looks expensive — beloved by ‘Secret Strategist’ readers.
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