There has never been a better time to be a guy in his 50s who wants to dress well. You can see it in Esquire, where interior designer Alfredo Paredes demonstrated recently that a gently advanced age is no barrier to great style. And you can see it in the various ad campaigns of major fashion brands, which are featuring men in their 50s (and older) more frequently. J. Crew, for instance, just made 51-years-young Oscar winner Adrien Brody the face of its new menswear collection.
In fact, right now, almost all of Hollywood’s best-dressed men are in their 50s: Colman Domingo, Javier Bardem, Vincent Cassel, Walton Goggins … the list goes on.
There’s an ease that comes with age—and a sense of selfhood that’s established over decades of style mistakes and style victories. Lessons learned, in other words. But there can be pitfalls too. Great clothes are for everyone, but cutting-edge trends are usually a younger man’s game. What you need in your 50s is a concise, reliable, low-intervention arsenal of pieces and styling hacks that will make you look and feel good, without even a thought for the minefield of avant-garde fashion.
Keep It Simple—and Elegant
Here’s the most straightforward style hack for getting dressed in your 50s: Find a simple yet elegant combination that can be dressed up or down and stick to it.
Jeremy Langmead—a writer, consultant, and former editor in chief of British Esquire—figures he’s seen hundreds of fashion shows in his life. This can be hazardous to your personal style. Langmead admits he’s fallen for fashion trends that haven’t aged well. In his 50s, however, his wardrobe has simplified. “I’ve found the pieces that work, stocked up on them, and mostly stick with a uniform,” he says.
Langmead keeping it simple.
Langmead’s uniform consists of pleated navy trousers, a striped or plain white T-shirt, a sweatshirt or simple cashmere crewneck, and white sneakers. It’s “versatile, no-brainer, hybrid dressing that works anywhere for almost any occasion,” he says. The only time Langmead gets “adventurous,” he says, is when true adventure is on the cards: mountains, trails, hiking, etc.
Most modern lifestyles would suit a wardrobe like Langmead’s. It’s easy and comfortable; it can be dressed up and down when necessary. For instance, you can swap out the white sneakers for derbies or boots. You can throw a soft-shouldered blazer over the cashmere knit to take things up a notch. It’s great for a day at home, a day of travel, and a day of meetings. It also toes the line between formal and casual perfectly and means you’ll feel put together but not overdressed. As guys age, they tend to default to dressing up or dressing down. The former is preferred to the latter—David Bowie nailed the dressed-up look when he adopted more tailored outfits as he aged—but it is possible to build a wardrobe that is both formal adjacent and easygoing.
Matt Damon, then 52, walking the line between formal and casual at the Oppenheimer premiere in 2023.
In this milieu, denim should be slim (but not skinny) and not distressed, shirts are soft collared and collegiate, and sneakers are low-key and retro inspired—more timeworn Sambas than Jordans fresh out of the box. You’re looking for what the menswear industry calls “elevated essentials,” which are the building blocks of a great wardrobe but are made to last and improve as you wear them: beautiful knits, heavyweight tees, simple but sumptuous tailoring, timeless overcoats. The brands that do this best are, unsurprisingly, on the more expensive end of the spectrum, but paradoxically, they also offer great value. You could spend less on a cashmere sweater that will develop pills after your first wear or invest a few hundred more for a sweater that will last years (as long as you keep the moths away). Some of the brands to shop include Massimo Alba, Officine Générale, Beams Plus, Sunspel, Lemaire, Oliver Spencer, Ralph Lauren, Drake’s, and Todd Snyder. If your budget allows, consider luxury brands at the even higher end like Brioni, Brunello Cucinelli, Hermès, and Loro Piana.
Adopt a Uniform
The notion of a uniform is worth considering, too. Albert Einstein, Steve Jobs, and Tom Wolfe wore pretty much the same thing every day. Doing so establishes a staunch personal style and releases you from the daily rigmarole of getting dressed. Style without thought, essentially.
Sure, you might avoid wearing a white suit every day (like Tom Wolfe) or owning a closet full of turtlenecks and New Balance sneakers (like Steve Jobs), but consider sticking to variations of the pieces you know work for you: a navy blazer or chore coat, a pair of boots, or simply a peacoat. Men are lucky because people tend not to notice them wearing the same thing every day, so why not lean in?
12 Great Picks to Wear in Your 50s
Officine Générale Pierre Pants
Folk Classic Striped Cotton-Jersey T-Shirt
Auralee Super Kid Mohair Sweater
Portuguese Flannel Labura Cotton-Corduroy Overshirt
Red Wing 8084 Heritage 6″ Iron Ranger Boots
Orlebar Brown + 007 Camp-Collar Zebra-Print Linen Shirt
Lemaire Light Tailored Overcoat
Marni Logo-Embroidered Striped Brushed Mohair-Blend Sweater
Gant Regular Fit Classic Striped Oxford Shirt
Suitsupply Mid Blue Straight Leg Jeans
Jil Sander Buttoned Denim Shirt
Langmead, the former British Esquire editor in chief, also suggests that men in their 50s (and beyond, we can assume) could always punctuate a simple, understated wardrobe with odd styling touches that help to lift an otherwise low-key look. “Bright pops of color—sweaters or sweatshirts—can bring an outfit to life,” he says, “and simple white sneakers make formal suits and trousers appear more youthful.
“I love it when you see older guys going for it with pattern, color, and silhouette,” he adds. Elasticated or drawstring waistbands can be your friend, he says, especially when snacking.
There are hazards, of course. Fluorescent colors and animal prints, for example, can serve as the perfect accent to a look, but rarely do they work as the main event. The same goes for unorthodox shapes and pieces that are simply designed for a younger, more capricious demographic. Langmead admits to the misuse of elongated, statement knitwear and sneakers that “shouldn’t have seen the light of day.” Ultimately, he’s anti-prohibition and suggests that there is no strict doctrine for what you can and cannot wear, whatever your age.
“The rules are no longer potent, age is less meaningful, and when you get older you give less of a damn what others think.” he says. “Wear what you want.”
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