The Secrets to Dressing Well in Your 60s

For proof that men in their sixties, and beyond, can still be stylish, you need only look at the boardrooms of the fashion industry itself. British founder-designer Sir Paul Smith, seventy-nine, is a walking billboard for the well-cut navy suit. And at the spritely age of eighty-five, Mr. Ralph Lauren is testament that the innate sense of adventurous pleasure that style offers—be it westernwear, classic prep, or even slick Wall Street tailoring—is open to all, whatever age they may be.

But some of the latest big-ticket ad campaigns have highlighted a specific demographic: men in their sixties. Designer Peter Saville, sixty-nine, appeared in a Ferragamo campaign recently; watch collector Auro Montanari, sixty-seven, was in a recent Zegna campaign. Actor Richard E. Grant, sixty-eight, took the runway with aplomb for Burberry. Hollywood offers even more inspiration: sixty-four-year-old George Clooney, sixty-one-year-old Brad Pitt, and sixty-eight-year-old Spike Lee remain among the stylish men in showbusiness. It seems sexagenarians have never been cooler.

The sixty-eight-year-old actor Richard E. Grant and his daughter Olivia head into a party after the Burberry fashion show in which he modeled.

So what does that mean for you, a man in his sixties, looking to improve his style game? The good news is that your experience—perhaps even wisdom—combined with your income means your sixties could be your best-dressed decade. Here’s how to do it.

First, make no sudden moves. New York-based personal stylist Peter Nguyen works with professional guys in their sixties. He says the most common mistake they make is “wearing things the young kids wear in an attempt to look younger or in style.” That might be a pair of hype-heavy sneakers, a piece that’s metallic or sheer, or heavily branded garments—clothing designed to draw attention to the wearer’s engagement in the zeitgeist, essentially. But what’s cutting-edge-cool for a twenty-something kid probably won’t be right for you.

Peter Saville and Auro Montanari represent a laid-back, almost cozy chic that’s ideal for their sartorial generation. Soft tailoring, roomy but well-cut pants, delicate knitwear, and the odd flourish here and there (an out-there pair of glasses, perhaps, or a droolsome watch) stave off any overall banality. Their style is timeless, rather than trendy.

The sixty-nine-year-old Peter Saville represents a laid-back, almost cozy chic.

That said, Nguyen sees clients that assume certain youth-skewed pieces, like leather jackets or even sneakers, are off limits. And that just isn’t the case. It might be worth avoiding the latest fluorescent wraparound shades, but a classic leather bomber could be just the ticket. “I totally understand the fear older guys have of looking like they’re trying hard to look young,” says Nguyen. “The secret is pulling from an authentic place. Jeff Goldblum can pull off the edgy-with-a-bit-of-quirk outfits because he’s always been a bit of a quirky guy with edge.”

Jeff Goldblum, who isn’t in his sixties (he’s seventy-two), is a more adventurous dressers, which is authentic to who he’s always been. That’s key to dressing well at any age: be authentic.

Start with some introspection. What kind of style are you looking to achieve, and how can it marry with the way you dress now? Perhaps you want to make a major change, but how would it work with your day-to-day lifestyle? And are there guys like Goldblum or Grant, that you’d like to emulate?

Once you have the groundwork nailed, it’s important to understand how your clothes should fit. Generally, as guys get older, their bodies change, and in turn, clothes tend to get a little looser, which is fine. There is an assumption that “cool” means a slim or skinny fit, and that's just wrong. In fact, skinny fits rarely look good on anyone, regardless of age.

Nguyen is a firm believer in the “rule of thirds,” which denotes that your pants should equate to around two-thirds of your outfit’s total height, so your waistband should probably hit somewhere around the belly button, especially on more formal pants.

“I think all guys should be wearing their pants with a higher rise to get that two-third legs proportion that’s extremely flattering,” he says.

Guys in their sixties should look for paints with a little room and a single pleat that hit around the belly button. Take inspiration from Steven Taffel, sixty-eight, owner of the high-end shoe store Leffot, who was photographed for the Esquire series Five Fits.

Skinny pants with a higher rise look especially insane, so opt for pants with a little more room in the leg. You don’t necessarily need to go for the very full width that’s been on trend for a while now, but a regular straight fit would work.

Younger guys might marry those wider-leg pants with a slightly cropped top—maybe a tee or button-up shirt—but the smart play for older guys is to go classic. A cashmere crew neck knit, for example, or even just a great oxford cotton button down shirt, tucked into the waistband, with a soft, unstructured jacket or overshirt on top. Suit Supply has a great range of soft-shouldered jackets that look like a blazer but feel like a cardigan.

Overall, err on the more formal side. That doesn’t require wearing a suit every day—though Sir Paul Smith’s uniform of a simple navy suit and open-neck shirt is a solid, fuss-free option—but it does mean soft-collared shirts or knitted polos instead of T-shirts, corduroy or linen pants over denim jeans, and unlined, easy-wearing sport coats over techy outerwear. You’re looking to come at modern style from a more timeless perspective, and trying to achieve a look that says “I know what I’m doing,” rather than, “I’m trying to look younger.”

The designer Paul Smith, who’s seventy-nine, wears an unfussy navy blue suit and white shirt without a tie.

It’s a kind of studious ease that was perhaps best typified by Oscar Isaac in the 2021 HBO series, Scenes from a Marriage. Isaac is not even 50, and was even younger then, but stylist Miyako Bellizzi created a wardrobe that completely nailed older-guy style: sumptuous, earthy colors, comfortable fits, and fabrics that speak of taste and good craftsmanship. Bellizzi mixed together pieces by Prada, Fear of God, Beams, Dries Van Noten, Loro Piana, and New Balance. (And note the use of high/low styling—a neat trick for older-guy style.)

Oscar Isaac in the 2019 HBO series Scenes From a Marriage. Although he wasn’t even 50 when shot the series, his style exemplifies great older guy style

Nguyen recommends investing in a pair of high-rise, single pleat pants in a neutral color—a “wardrobe workhorse that upgrades any outfit,” he says. Add to that a chambray shirt in a darker shade of blue, which is both “flatteringly masculine” and "extremely versatile,” and a pair of minimal sneakers in either white or mid-brown suede. “A lot of my older clients have switched to less stylish and more comfort-focused sneakers,” he says. Minimalist sneakers—like those made by Greats, Zegna, and many other brands (here are some Esquire recommendations)—are a huge and simple upgrade.

If that all feels a little bland, consider adding flourishes with poppy accessories. Spike Lee does it with out-there spectacles, and George Clooney, a consummate low-key dresser, is also equipped with an Omega watch that perk up his outfits. Even a well-chosen ball cap can breathe life into an otherwise understated outfit. Just avoid that pair of Air Max.