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Smart Style Secrets From 3 Male Fashion Influencers Over 50
Colorful shirts, heavyweight tees, cardigans, vests and classic footwear sharpen everyday looks
8-minute-read
(From left) Fashion influencers Jason Jules, Tim Conlin and Wil Calhoun Jr. encourage men to find the right styles, shades and cuts that flatter and feel good for age 50 and beyond.
AARP (Getty Images, Mariana dos Santos, Courtesy Tim Conlin, Courtesy Wil Calhoun Jr.)
Key takeaways
- Personal style can remain expressive and individual throughout your 50s, 60s and beyond.
- Choose white jeans, colorful shirts and cosy layers to bring energy to classic wardrobe staples.
- Swap sneakers for comfy loafers and stylish boots with traction soles.
The internet is awash in men’s fashion content, but most of it skews to the younger guy. But how about some equal time for us 50-plus fellows? Taking up that sartorial challenge, we queried three men who make smart dressing an important part of their business as menswear observers. When asked about their style secrets and go-tos for getting dressed, they gave plenty of answers — some rooted in the classics, others with more than a few surprising swerves.
But they all voiced the same attitude about dressing for your 50s, 60s and beyond: There’s no need to forgo personal style as you get older. In fact, this is the time to take some pleasure in the way you greet the world every day. And by setting a well-dressed example, maybe you’ll show those younger bucks a thing or two about style.
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(From left) Lands’ End Stretch Comfort-Waist Easy Classic Fit Natural Jean in Undyed Natural; Madewell 1991 Loose Straight Jean in Ecru Rigid.
AARP (Lands’ End, Madewell)
Jeans scene
Dallas-based Tim Conlin, a menswear designer turned creator (@tim.conlin), 60, projects a confident style that favors classic pieces put together with an eye for crisply contrasting elements. “My wife says my three favorite colors are blue, blue and blue,” he jokes, but his Instagram grid reveals an eclectic view, with shots of red, multicolor madras and a pink-striped rugby in the mix. One of his favorite tricks for making a look pop is to play those pieces against his go-to white jeans. “Some guys say, ‘Oh, they get dirty,’ but I throw them in the wash just like my blue jeans,” Conlin says. “I wear white jeans year-round, and they’re a great neutral that goes with everything.”
The ol’ reliable (and Conlin’s pick), Levi’s 501 Original Men’s Jeans ($51, levis.com) feature the timeless straight fit and classic button-fly in non-stretch cotton denim. For a roomier fit, Madewell’s 1991 Loose Straight Jean ($148, madewell.com) comes in a versatile ecru cotton denim. The Lands’ End Stretch Comfort Waist Easy Classic Fit Natural Jean ($90, landsend.com) adds extra wearability to undyed denim and easily spans the seasons.
Old Navy Waffle-Knit Beanie for Men in Mystic Fire.
Old Navy
Bright done right
Speaking of color, the most unexpected shade to juice up a look is a hit of brazen orange, as seen in, say, a casual shirt jacket. As Conlin explains, it’s not really a step too far. “Beyond blue, orange is probably one of my favorite colors, just because it has that kind of visual impact,” he says. “You also equate it with ‘safety orange’ and hunting, so there’s some masculinity. With orange, you’re going all in.”
Line of Trade’s Melton Overshirt ($148, bespokepost.com) warms with its deep orange colorway and brushed, felted wool-blend fabric adapted from vintage naval wear. For adding a pop of color to any chilly day, there’s Old Navy’s Waffle-Knit Beanie for Men ($7, oldnavy.com). Updated with a roomier rise and a comfort waistband, Eddie Bauer’s Men’s Guide Pro 2.0 Pants ($35, eddiebauer.com) feature reinforced pockets and a tapered fit that’s well suited for hiking trails and urban trekking.
(From left) J.Crew 1990 MacAlister Boots in Suede; Sperry Newman Chukka Boot II in Bordo.
AARP (J.Crew, Sperry)
Style to boot
Conlin varies his footwear, which includes loafers, novelty slippers, and, it being Texas, the occasional pair of cowboy boots. “On the other hand, I’m obsessed with old-school canvas sneakers like Tretorns and Vans,” he says. “And then in the fall, I like a chukka boot. I can’t tell you how many pairs of J.Crew MacAlister boots I’ve owned over the years.”
Crafted from Italian suede with a crepe sole, J.Crew’s 1990 MacAlister Boots ($198, jcrew.com) offer comfortable, casual style without sacrificing footwear finesse. The Johnston & Murphy Seth Chukka Boot ($140, johnstonmurphy.com), in mahogany full-grain leather, features a comfort-foam footbed for a springier step and a rubber sole for wearability and traction. Sperry’s Newman Chukka Boot II ($60, sperry.com), with a genuine nubuck leather upper, has a lightweight insole for long-wearing comfort and a molded outsole for traction on wet or dry days.
(From left) Gap Denim Shirt in Medium Wash; Banana Republic Factory Standard-Fit Denim Heritage Shirt in Dark Rinse; L.L.Bean Men's Sunwashed Denim Shirt, Slightly Fitted in Medium Wash.
AARP (Gap, Banana Republic Factory, L.L.Bean)
Buttoned up
“Never knowingly underdressed” is the motto top-lining Jason Jules’ Instagram feed (@garmsville), which is no surprise given that the 62-year-old is also the author of the 2021 book Black Ivy: A Revolt in Style. Jules takes his classic sartorial cues from the greatest generation in the postwar years, when Ivy style really took hold.
“That generation was forward-thinking, and these clothes represented something forward-thinking,” he says. “They were very modern in that sense. You know, jazz musicians all wore these clothes, and lots of very cool artists wore these clothes, from Andy Warhol down to Lichtenstein.” Any number of button-downs are a shirt staple for Jules. “They never go out of fashion,” he says. “If you want to be a bit more style-conscious, then definitely a denim shirt’s going to work.”
With a straight and easy fit, the Gap Denim Shirt ($34, gap.com) is a men’s wardrobe essential in a medium blue that especially complements silver hair. The Banana Republic Factory Standard-Fit Denim Heritage Shirt ($43, bananarepublicfactory.gapfactory.com) takes a darker tack, with pure cotton denim in a black-wash coloration, and is styled with twin chest pockets. For a weathered, casual look, get a head start with the L.L.Bean Men’s Sunwashed Denim Shirt, Slightly Fitted ($60, llbean.com), that looks great as an untucked outer layer.
(From left) Goodfellow & Co Men's Every Wear Straight-Fit Chino Pants in Tan; Lands’ End Knockabout Comfort-Waist Classic Straight-Fit Chino Pant in Forest Moss; Brooks Brothers The Friday Chino in Green.
AARP (Target, Lands’ End, Brooks Brothers)
Primo chinos
“The great thing about preppy, or Ivy, is that there’s always a level of quality that never goes beneath because it’s a series of staples,” says Jules. “It’s pretty pointless for a manufacturer to mess up with a pair of chinos.” He favors mid- to high-waisted models with a flat front “that will never fail you.”
Good for any day of the week, Brooks Brothers The Friday Chino ($148, brooksbrothers.com) is washed after construction for a soft, lived-in feel. For long-day comfort, Goodfellow & Co’s Men’s Every Wear Straight-Fit Chino Pants ($35, target.com) bring a straight fit in a breathable cotton twill with slight stretch for added flexibility. The Lands’ End Knockabout Comfort Waist Classic Straight Fit Chino Pant ($36, landsend.com) features a crisp look with extra ease through the hip while remaining straighter through the thigh. A bonus: The waistband offers up to 2 inches of extra roominess hidden inside.
(From left) J.Crew Soft-Washed Wool Sweater in Heather Green Apple; Pendleton Shetland Crewneck Sweater in Black Heather; L.L.Bean Men's Heritage Honeycomb Sweater, Crewneck in Dark Bronze Heather.
AARP (J.Crew, Macy’s, L.L.Bean)
Sweater weather
“I’ve always dressed in this [Ivy] style since I was a kid,” says Jules. “There’s a strictness about it, but there’s also a playfulness.” He adds, “It’s youthful because there’s more color and it has its roots in college campus style.” One of his favorite pieces is a wool Shetland pullover, a durable go-to that runs the gamut of colors from game-day brights to rich earth tones and grays.
With a substantial heft and a washed texture, J.Crew’s Soft-Washed Wool Sweater ($158, jcrew.com) adds a pop of color in a versatile apple green. Pendleton’s Shetland Crewneck Sweater ($90, macys.com) in heathered stone gray is crafted from water-resistant pure wool. The L.L.Bean Men’s Heritage Honeycomb Sweater, Crewneck ($80, llbean.com) adds a textural twist to the classic 100% lambswool crewneck, and the dark bronze color adds a nice topper to any outfit.
(From left) L.L.Bean Vintage Soft Rugby, Chest Stripe in Oatmeal Heather; Goodfellow & Co Men’s Long-Sleeve Rugby Shirt in Dark Green.
AARP (L.L.Bean, Target)
A rugby revival
Wil Calhoun Jr. (@charmcityprep), 50, grew up in Baltimore, the son of a now-retired Baptist minister and his late mother, who worked for nonprofits. “I grew up in the church, and I remember getting my first three-piece suit at age 5 — this god-awful tan color,” he recalls. “I’ve been dressing up for the majority of my life.” Under the moniker Billy Freshington, his social media account reveals a high-spirited take on his “urban preppy style,” though he doesn’t really think of himself as an influencer. “I just like wearing clothes and posting them for this community that follows me. Especially because I’m a man of a certain size, and it can be kind of daunting.”
One of Calhoun’s staples for adding some zip is a striped rugby shirt, because you can dress it up or down. L.L.Bean’s Vintage Soft Rugby, Chest Stripe ($80, llbean.com), in a navy color combo, has truly authentic styling, with rubberized buttons and a twill placket and collar. For a more citified take, Lululemon’s Long-Sleeve Rugby Shirt ($118, shop.lululemon.com), in solid olive brown, has a relaxed fit with a touch of stretch, made from a durable French terry blend. Sporting a bold, banner-green hue, the Goodfellow & Co. Men’s Long-Sleeve Rugby Shirt ($30, target.com) is made of a solid midweight cotton jersey.
(From left) Banana Republic Factory Weekender Quilted Vest in Sheltered Earth; L.L.Bean Commando Vest Sweater in Bright Navy Heather.
AARP (Banana Republic Factory, L.L.Bean)
Vested interest
Another one of Calhoun’s styling moves is adding a contrasting vest to his outfits. “I’ll even take a fishing vest and put it under a navy blazer with a shirt and tie — things that you don’t think would go together — and you’re putting your own spin on it.”
Crafted of 100% Irish wool, Alex Mill’s Coldbreaker Standard Vest ($115, alexmill.com) comes in a range of characterful colors, like a plum mix with contrast trim and a zip front. Adapted from the iconic sweater worn by the British forces in World War II, L.L.Bean’s Commando Vest Sweater ($80, llbean.com) makes for a warm and durable layer in gray heather lambswool with a cotton shoulder patch. Banana Republic’s Weekender Quilted Vest ($48, bananarepublicfactory.gapfactory.com), in forest green, has a quilted utility look combined with sweatshirt-like construction.
Banana Republic Factory Leather Penny Loafer in Cognac.
Banana Republic Factory
Loafering about
Calhoun, a job coach for the city of Baltimore, was a big sneakerhead for years, but these days the Jordans and Adidas are gathering dust on the shelf of his shoe closet. “What’s crazy is now I get more comfort out of a pair of Weejuns. I have some that are old and broken-in and they feel like socks,” he says. “Six out of seven days, I’m in loafers.”
A lodestar of American style, the Bass Larson Weejuns Penny Loafer ($195, ghbass.com), in traditional wine, boasts fine craftsmanship with hand-stitched moccasin construction. Cole Haan’s American Classics Penny Loafers ($170, colehaan.com), in an updated chocolate tone, have a lug sole that offers a cushioned step. The sleek Banana Republic Factory Leather Penny Loafer ($99, bananarepublicfactory.gapfactory.com) is a classic rendition with a notched penny strap and apron toe in golden cognac leather.
The key takeaways were created with the assistance of generative AI. An AARP editor reviewed and refined the content for accuracy and clarity.
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