How Men Can Level Up Their Style Game and Look Youthful in Their 50s and Beyond

Grooming and fashion tips to help guys feel their best — and look even better

Vincent Boucher,

AARP

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Published June 19, 2025

(From left) Izod Performance Polo in Peacoat; Sperry’s Moc Neo Boat Shoe in Tan; J. Crew Short-sleeve Shirt in Cotton-Linen Blend in Batik Brown Blac; Brooks Brothers’’ Rubber & Leather Belt With Stretch in Light Orange; Lands’ End No Iron 9" Comfort Waist Plain Front Chino Short in Khaki.

AARP (Kohl’s, Sperry, J. Crew, Brooks Brothers, Lands’ End)

Navigating the minefield of personal style can be a little daunting in a man’s middle years, but making the effort more than pays off — and it’s worth the time and investment.

Start by taking a good look in both the mirror and your closet to set yourself on the right path. We’ll get to the personal grooming in a minute, but as far as fashion goes, staying current is key. You’re long past worrying about the latest trends, of course, but men’s fashion does change, almost imperceptibly, from decade to decade. That means at this vantage point — a quarter of the way into the 21st century — any wardrobe veterans from the ’80s or ’90s are likely out of date.

The best strategy for staying relevant looks-wise means relying on menswear classics — there’s a reason they’ve been around so long — in updated versions that offer an unbeatable equation of reliable and functional style. We’ve got some easy and accessible suggestions that’ll get you started, but always make the midlife style trek your own.

Oars + Alps Everyday Anti-Aging Face Moisturizer SPF 37

Oars and Alps

Mirror imagineering

Younger guys can get away with a catch-as-catch-can look, but at 50 and beyond, your grooming play should be tight and crisp. If you don’t have a regular relationship with a barber or stylist, now is the time, and keeping your hair consistently trimmed always complements a silver crown. On the other hand, if you’re losing it, don’t hang onto those side wisps — go for a cleanly shaved pate à la Messrs. Tucci, Stratham and the Rock.

Regular skin care is also a must, even if at first you only start with a daily face-wash-and-toner routine. To keep your visage supple and vibrant (aging can cause dryness and loss of tone), always start the day’s activities with a light layer of moisturizer with sunscreen. Kiehl’s Facial Fuel Men’s SPF 20 Moisturizer ($33, kiehls.com) re-energizes skin in a nongreasy formula with antioxidant benefits. Harry’s Men’s Face Lotion ($10, target.com) hydrates the skin without leaving it greasy and offers broad-spectrum SPF 15 protection. For a higher sunscreen, Oars + Alps Everyday Anti-Aging Face Moisturizer SPF 37 ($19, macys.com) features moisturizing hyaluronic acid and antioxidant-rich ingredients.

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(From left) L.L. Bean’s Ultralight Adventure Polo in Light Mahogany; Izod Performance Polo in Peacoat; J. Crew Sueded Cotton Polo Shirt in Dusty Charcoal.

AARP (L.L. Bean, Kohl’s, J. Crew)

Ditch that tee

You might think, even as you get older, that wearing a T-shirt gives off a youthful vibe, but what’s better is a knit shirt with a face-framing collar that puts the emphasis on your mug and draws attention away from the blurry chin line and turkey neck that inevitably come with the years. Here are some lightweight choices that are comfy as a trusty ole tee but a helluva lot more flattering, starting with L.L. Bean’s Ultralight Adventure Polo in Bright Sea Blue or Light Mahogany ($50, llbean.com) in a moisture-wicking, UPF 50-plus cotton blend. Another good bet is the pure cotton J.Crew Sueded Polo Shirt in Dusty Charcoal ($50, jcrew.com) with a smooth handfeel that packs a lot more polish than a standard T-shirt. Similarly, the Izod Performance Polo in Navy or Peacoat ($20, kohls.com), in a breathable cotton blend, keeps its shape all day long.

(From left) Richmond Pant from Brooks Brothers Gray; Gap’s City Jeans in Straight Fit in Forbidden Forest and Fannel Taupe.

AARP (Brooks Brothers; Gap, 2)

Jettison the (blue) jeans

Many guys find five-pocket pants comfortable and flattering, but at a certain point denim starts to skew too young, and clinging to those faded blues runs the risk of putting yourself in dreaded “dad jeans” territory. Keep the ease and versatility of the style while raising your game with jeans-cut casual trousers in sharper, solid-color versions. Consider the Richmond Pant from Brooks Brothers in Olive or Gray ($148, brooksbrothers.com), crafted in primo Italian cotton fabric. Gap City Jeans in Straight Fit in Flannel Taupe or Forbidden Forest ($48, gap.com) are a jean/khaki hybrid with a classic straight leg and comfortable flex fit. Polo Ralph Lauren Varick Slim Straight Jeans in Boating Khaki or Classic Stone ($48, macys.com) tread a middle ground with a regular rise and straight leg that tapers slightly below the knee in a washed and garment-dyed cotton that feels already broken-in.

(From left) J. Crew Short-sleeve Shirt in Cotton-Linen Blend in Batik Brown Blac; Nautica’s Printed Tropical Button-Up Camp Shirt in Ocean.

AARP (J. Crew, Macy’s)

Prints for a ‘fit’

Call them tropical or resort shirts, but donning an unexpected print or a graphic stripe takes the starch out of a summer suit. It also suggests you’ve still got it when it comes to personalizing your own style, as memorably shown by 69-year-old actor Bryan Cranston on his recent press tour for Apple’s streaming series The Studio. Paired with a solid navy or khaki suit, Banana Republic’s Luxury-Touch Resort Shirt in Seaport Blue ($80, bananarepublic.com) combines cotton stripes with a straight and easy fit for warm-weather panache. Catch an island vibe with a breezy, batik-print J.Crew Short-sleeve Shirt in Cotton-Linen Blend ($65 jcrew.com) whose brown-and-black colorway sparks up a gray or white suit. Or go all out this season with a splashy floral to wear under a blazer or suit, like Nautica’s Printed Tropical Button-Up Camp Shirt in Ocean Garnet ($56, macys.com) in an airily soft viscose-linen blend.

(From left) Brooks Brothers Rubber & Leather Belt With Stretch in Light Orange; Sid Mashburn’s NATO Watch Strap in Ginger Yellow.

AARP (Brooks Brothers; Sid Mashburn, 2)

Add a pop of color

A colorful accessory adds a bracing counterbalance to our mostly neutral wardrobes. A woven belt in unexpected orange wakes up, say, a tan pair of slacks; a ginger yellow band adds some fizz to that same old watch. And pulling out a credit card from a multihued leather case really shows you have some (calf) skin in the style game. Brooks Brothers’ Rubber & Leather Belt With Stretch in Light Orange ($98, brooksbrothers.com) features a woven construction with leather trim and some flex for all-day comfort. Sid Mashburn’s NATO Watch Strap in Ginger Yellow ($15, sidmashburn.com) suits luxury and utilitarian timepieces alike and has a novel backstory: Its durable nylon strap with polished-steel hardware started as standard issue for the British Ministry of Defense, and the style hasn’t been tinkered with since. Hyer Goods Upcycled Italian Leather Certo Card Wallet in Red or Vert Anis ($80, nordstrom.com) is cunningly crafted in a modernist colorplay of leftover genuine Italian luxury leathers.

(From left) Lands’ End No Iron 9" Comfort Waist Plain Front Chino Short in Khaki; Polo Ralph Lauren’s 10-Inch Relaxed Fit Chino Short in Newport Navy; Banana Republic Factory’s 10” Summerweight Denim Short in Ecru.

AARP (Lands’ End, Ralph Lauren, Banana Republic Factory)

Try the Bermuda angle

Menswear designers have been promoting thigh-baring shorts the last couple of years, but one of the prerogatives of mature style is leaving the trends to the “kids” — and good riddance! Knee-length Bermuda shorts still give the cooling benefit while remaining fashionably age-appropriate. The Lands’ End No Iron 9" Comfort Waist Plain Front Chino Short in Light Stone and Khaki ($80, landsend.com) is a plain-front style that stretches up to 2 inches in the waist for added ease. Polo Ralph Lauren’s 10-Inch Relaxed Fit Chino Short in Newport Navy or Sandsurf ($90, ralphlauren.com) in 100% cotton pairs well with either loafers or tennies. Or switch things up with Banana Republic Factory’s 10 Summerweight Denim Short in Ecru or Dark Indigo ($42, bananarepublicfactory.com).

(From left) Dockers’ Rowe Men’s Canvas Boat Shoes in Navy; Sperry’s Moc Neo Boat Shoe in Tan; Lands’ End Comfort Leather Slip On Boat Shoes in Toasted Rye.

AARP (Kohl’s, Sperry, Lands’ End)

Rock the boat shoe

Sneakers offer reliable comfort, but if you’re looking for a similarly supportive shoe with a little more finesse, consider the new breed of boat shoes. Instead of a traditional flat rubber bottom, these variations incorporate improved innersoles for comfort and fit, as well as thicker but lightweight outsoles for traction and ergonomic support. The Lands’ End Comfort Leather Slip On Boat Shoes in Toasted Rye ($120, landsend.com) translates the brand’s popular canvas model in sturdy and soft nubuck, with a breathable mesh lining, removable EVA insole and durable, high-traction outsole. Sperry’s Moc Neo Boat Shoe in Tan ($60, sperry.com) features a stylish higher cut that pairs well with trousers and is made from lightweight synthetic materials, with a molded outsole for improved grip on wet surfaces. Dockers Rowe Men’s Canvas Boat Shoes in Navy ($40, kohls.com) also offer all-day comfort and support with a massaging EVA footbed designed to instantly adapt to a foot’s unique shape, plus a thick rubber outsole for dependable traction.

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Vincent Boucher is a fashion journalist whose writing has appeared in The New York Times, The Wall Street Journal, The Hollywood Reporter, the Los Angeles Times and New York magazine. Earlier in his career, he was the fashion director at Esquire and a celebrity stylist, and he remains a creative consultant.

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