How to Dress Your Age: The Essentials for Looking Good at Every Stage

WITH NEW AGE comes change, and that should be reflected in your wardrobe, too. You’re not going to wear the same thing at 40 that you wore at 25. Not because it’s “age-inappropriate”, but because your lifestyle matures, your body changes, and maybe, you want to look more pulled together. As a style editor in my 30’s, I’ve outgrown skinny jeans, graphic t-shirts, and ultra-flashy sneakers from my 20s for knit polos, tailored suits, and low-key shoes. And that’s a good thing.

Style in your 30s, 40s, 50s and beyond isn’t about chasing trends; it’s about building a uniform that works for your life now. Even Hollywood’s leading men have evolved their fashion game without losing what makes them feel confident. Take a page from A-list actors like Pedro Pascal, whose style has matured over the past decade. In his earlier years, he leaned into relaxed, laid-back looks with casual tees. Now in his 50s, he blends that cool vibe with sharper pieces. Think: rich textures, bold prints, and standout jackets that turn heads without trying too hard. He proves that aging in style doesn’t mean toning it down, but knowing how to take smarter risks.

If you’re unsure where your wardrobe should land, start by looking at these guys below. This isn’t a one-size-fits-all approach, but you can use their style as a jumping-off point for dressing your age while still making it your own. The goal isn’t to copy them. It’s to take inspiration and shape it around your own taste and lifestyle.

20s

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Most guys in their 20s default to oversized hoodies, baggy jeans, and beat-up kicks. It’s comfortable, sure, but it doesn’t always look put together. Still, there’s a way to embrace youth without looking sloppy, and Tom Holland is a great example. His red carpet fits lean tailored and clean, never too stiff. Off the clock, he keeps things casual without looking too boyish; think cropped jackets, sleek trousers, and clean sneakers. The 28-year-old’s style is a reminder that looking polished doesn’t have to mean dressing up; it just means knowing what fits and feels right.

L.L. Bean Premium Double L® Polo, Long-Sleeve Without Pocket

Saks Fifth Avenue Men’s Collection Cotton Long-Sleeve Polo Shirt Now 55% Off

Abercrombie Baggy Trouser

Axel Arigato Clean 90 Sneaker30s

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As you move through your 30s, your wardrobe should start reflecting more confidence and control, less about trying everything, more about perfecting what works. Michael B. Jordan nails that evolution, whether he’s suiting up for a film premiere or sitting courtside in streetwear. During his recent press tour for Sinners, the 38-year-old wore an open, one-button polo and dressy trousers that looked made for him: sitting right above his hips with a handsome drape that looks super classy. His style strikes a balance between active and elevated including tailored pieces with room to move and casual fits with luxe materials. Yes, athletic guys can also wear more relaxed fits without looking like a blob. Just make sure they’re tailored in the right spots including the shoulders, seat, and the hem.

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Suitsupply Off-White Buttonless Polo

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40s

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Hitting your 40s doesn’t mean dialing things back. It means leveling up with pieces that feel grown-up but still rugged. Alan Ritchson is a prime example of how to do that right. He leans into heavyweight jackets, worn-in leather, and strong fits that complement his giant frame, but never look overstyled. It’s the kind of fit that doesn’t need to say much. His approach shows that you don’t need to reinvent your wheel, but invest in pieces that are built to last and made to fit well.

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Todd Snyder Favorite Oxford Shirt

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On The Roger Spin 250s

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In your 50s, style isn’t about playing it safe; rather it’s about knowing the rules well enough to break them. Pedro Pascal has made that shift look easy, especially after going viral for his Cannes Film Festival look: a form-fitting muscle tee and dress pants. Early in his career, his fashion game leaned laid-back and low-key. Now, he’s cracked the code on wearing things that feel intentional, but don’t try hard. It’s another reminder that your fashion sense can evolve, and gets a lot more interesting when you’re not afraid to take risks.

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Madewell The 1991 Straight-Leg Jean

MENS LINCOLN BIT WEEJUNS LOAFER60s

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Once you hit your 60s, you’ve earned the right to wear whatever the hell you want. But when you have taste like Lenny Kravitz, it still hits with force. The 61-year-old singer mixes vintage, bohemian, and edgy pieces: leather jackets, cowboy boots, open shirts, and layers of jewelry. His rockstar style is fearless, but what sets him apart is the confidence behind it. The goal isn’t to dress young, but double down on what feels authentic. If you’ve got a signature look, own it.

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Tecovas The Buck70s

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By the time you’re in your 70s, style becomes second nature. You know what works, and you don’t overthink. That’s exactly where Denzel Washington sits. Decades in, his wardrobe doesn’t chase trends. He’s mastered understated cool: clean lines, classic fits, and a no-fuss approach that never tries too hard. You’ll find him in structured jackets, crisp shirts, and dress sneakers that speak volumes by doing less. At his age, Denzel proves that there’s strength in leaning into what works and that true style only gets better with age.

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As the Style and Commerce Editor for Men’s Health, Joseph covers all-things fashion and grooming. Previously, Cheatham was a commerce editor for Spy, and he has written for Travel + Leisure.

Christian is the deputy commerce editor at Men’s Health and Women’s Health, where he oversees shopping content for both brands. He started his magazine career as an accessories assistant at Vogue, and has since held editorial roles at Tatler Asia and The Manual. When he’s not online shopping, you can find him on long walks with his two corgis.