Are You Too Old to Wear That Now?

WE ALL TIRES one way or another during lockdown. Some men became fathers, celebrated milestone birthdays or changed jobs. And everyone got older.

As we re-enter a world of increasingly opaque dress codes, some people wrestle with how to dress in a way that makes sense for who they are now.

In the following, two authors from different generations are looking for solutions. Plus, find the jeans that are right for all ages and read about the worst style mistakes older men can make.

The guy in his 30s: Jamie Waters

I swam into the pandemic, still in my 20s, in a pool of oversized clothes. I threw big knits over big t-shirts, baggy pants and puffy sneakers. I turned 30 during lockdown – blowing out candles in a park while being eclipsed by an oversized paisley hoodie – and in the months that followed, a seed of doubt began to sprout: Was I my teenage wide Outgrown wardrobe?

THE MILLENNIAL GUY Model Bradley Evans wears: Connor McKnight T-shirt, $125,; Pants, $345,; watch, $925,; Shoes, $335, On Wyatt the Pup: Collar, $690, Leash, $920,

When I showed up to a post-lockdown dinner in a t-shirt that reached almost my knees, I asked a friend if I resembled an “overgrown skater boy”. She blurted out, “You absolutely don’t!” Her eyes darted to her menu in a way that confirmed I absolutely did. I began retiring items that felt forced now that I had entered my fourth decade: a hoodie with awkward, protruding pockets high up on the sleeves; an alphabet soup made of logo sweaters.

I traded my chunky sneakers for chunky Blundstone boots whose comfortable, no-nonsense sturdiness suggests I get things done. And I tried to stick to a sober, all-navy uniform that signaled efficiency. I was a busy adult, I told myself, and didn’t have time for teenage clothes. Then I got bored and in a moment of weakness I bought a sweatshirt with a huge embroidered avocado with eyes on it. I can’t take it off

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“There’s a difference between growing up and getting old,” said Jian DeLeon, Nordstrom‘s

Menswear and Editor-in-Chief. Obviously I had pushed the boring minimalism thing too far, but the underlying vibe was right. By my 20s, I had embraced the graphic prints, bold logos, and relaxed silhouettes that dominated much of menswear. Now, like many of my millennial peers, it was time for my style to mature.

I have many options for my rebranding: The menswear market is full of clothes for boys who are fed up with streetwear that is particularly edgy. There’s even a growing category of brands dubbed “post-streetwear.” Her collections often mix formal tailoring with well-known streetwear references and artful textiles; Mr. DeLeon cites 4SDesigns and 18 East as two standout brands.

Have fun, but also go to a tailor. In your 30s you realize that fit is key.

I’m drawn to New York’s corridor, which creates intrigue with textures rather than logos. Founder Dan Snyder said he likes knitwear because it allows you to play with dimensions, “almost like sculptures”. His cardigans combine yarns of different colors (pink, green, gray) and weights to make the eye dance. They’re smartly cool — and Mr. Snyder, a 37-year-old dad who lives in Brooklyn, wears them as a whimsical alternative to blazers. “It’s a way of layering without being serious,” he said. Another irreverent option: Kapital, a Japanese brand that spray-paints their jeans with raver-esque smiley faces.

Have fun, but also see a tailor, said Los Angeles stylist Chris Kim. Your 30s are when you “realize that fit matters.” To amp up your look, he advised getting a few key pieces made to measure, including a blazer and pants.

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My friend Tom Reynolds, an editor at a London magazine, has sharpened his style since becoming a father in lockdown. His goal: “cool dad, not lame dad.” Choose a vintage Paul Smith trench coat and a shoulder bag from Manhattan Portage, a brand that’s intriguingly obscure and unhyped, he said, so there’s no risk of that he looks like a victim of the streetwear trend.

To be taken more seriously, Mr Reynolds, 35, also bought his first pair of loafers. “I wore sneakers non-stop, so I was like, ‘I need to work this out,'” he said. He opted for brown textured-leather penny loafers that exude sophistication. There’s just one problem: They hurt too much, he said. After two flinching outings, he’s back in his Nikes. Growing up is tough. I’ll get him some Blundstones.

The man in his 60s: Vincent Boucher

I was in Midtown Manhattan the other day thinking about new clothes for fall, so I ducked into Saks Fifth Avenue. I remembered the earnest young Midwestern man who moved to New York in the 1980s and bought an Italian linen suit in the sixth-floor men’s enclave of Saks. I hadn’t landed my first job yet, but Milan tailoring was all the rage and I had to get involved.

THE OLDER MAN model Garrett Swann wears: Overshirt, $2,490,; T-shirt, $115,; Pants, $1,950, available October,; Loafers, $995,; Glasses, model’s own. On Rugby the dog: Leash, $410,

Today, the sixth floor is no longer wood-paneled and showcases a sea of ​​designer sneakers. The Italian tailors are still there, but they hide in the shadows: like other retailers, Saks no longer whispers the soft language of suits and sports jackets, but comes with bold luxury streetwear and chic everything.

If you’re in your 50s, your first reaction to creeping casualization might be to slip into your familiar suit. Traditional tailoring can be a safety net for older gentlemen. But this 69-year-old thinks branching out is fun. Check out Brad Pitt, 58, having the time of his life on the Bullet Train press tour, wearing a skirt to one premiere and an orange outfit to another. When a reporter asked why, Mr. Pitt said, “I don’t know! We’re all going to die, so let’s screw it up.” That’s as good a style creed as I can imagine, especially after being locked inside for so long.

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Post-lockdown, such freewheeling thinking is popular among the silver-haired group, New York-based stylist Jim Moore said. Many “older” men, he noted, want to ditch the quilted vests and chinos that are common among their peers. According to him, they say, “I want to play in the new-style sandbox.”


What are your top tips for dressing your old age in style? Join the conversation below.

Hollywood style consultant Andrew Weitz suggests replacing a blazer with a statement shirt jacket—perhaps a gray cashmere version by Thom Browne. And Los Angeles stylist Jeanne Yang recommends a Rick Owens high-top sneaker for a quirky touch. Or do like stars like Ethan Hawke (51), Hugh Jackman (53) and Bryan Cranston (66). According to their stylist, Michael Fisher, all three tell him, “Let’s not wear a tie [or] the quintessential premiere suit.” Try a casual suit option with an elasticated waist instead; I’m eyeing one by Ami Paris with a roomy, swaggering cut.

To up the ante on fashion, consider Dries Van Noten, Prada and Yohji Yamamoto, iconic brands whose clothing can be worn by men of all ages. I recently spotted a black cashmere button-down from Dries. Part shirt, part cardigan, it’s simple but understated. I’ll need it – but in the pink alternative. Now is the time to be seen.

fashion styling by Lizzy Wholley; maintenance of Mirna Jose/See Management; models Garrett Swann/Bella Agency; Bradley Evans/Bella Agency; Dogs Rugby and Wyatt / All creatures great and small

Not sure where to start? Create an outfit around dark wash denim that’s versatile across generations.

ONE JEANS, TWO WAY Jeans, $250,


Styled by Jill Telesnicki


Our millennial dude pairs the generational jean with a cable-knit fisherman sweater that features texture instead of logos and bright but not puffy kicks.

sweater, $395,; Shirt, $350, Drake’s, 917-261-5005; Sneakers, $100,; socks, $21,; Belt, $125,


Styled by Jill Telesnicki


Without formal tailoring, our elderly gentleman mixes denim with a casual suede jacket, polo (less conspicuous than a button-down shirt), and soft Chelsea boots.

jacket, $1,498,; Polo, $1,395,; Eyeglasses, $795, Jacques Marie Mage, 310-881-9539; Boots, $945,; Belt, $1,050,


Styled by Jill Telesnicki

Five missteps by men over 50

We asked stylists for the worst faux pas they’ve seen


Victoria Tentler-Krylov

“Older guys wearing Allbirds sneakers with jeans, khakis or more formal pants. To be honest, don’t wear them at all – whatever you pair them with won’t look good.” – Cassandra Sethi, Personal Stylist, Los Angeles

“The client was a recently divorced banker in his late 50s. His Hair was dyed too dark for his complexion and he wore baggy sweatshirts and skinny jeans. Plus: a variety of jewelry that made him look like he was on multiple random spiritual journeys.” —José Ramón Reyes, founder of wardrobe consultancy Custom Project, New York

“Nothing is more unattractive than an elderly gentleman wearing one outdated, ill-fitting suit.”—Andrew Weitz, celebrity style consultant, Los Angeles

“In New York, I always notice that older men wear graphic t-shirts and embellished jeans. These work on younger guys; [on anyone else] it makes you look like you’re really trying to dress like the kids.”—Peter Nguyen, Personal Men’s Stylist, New York

Clothes too tight! I’m talking to you, Mr. Bezos.” – Michael Fisher, stylist, New York

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