Being stuck at home meant a relaxed dress code, but you may be a different person now. We're here to help hunt for cool, age-appropriate clothes.

We all matured in one way or another during lockdown. Some men became fathers, celebrated a milestone birthday or changed careers. And everyone got older.

As we re-enter a world of ever-hazier dress codes, some folks are grappling with how to dress in a way that makes sense for who they are now.

Here, two writers of different generations seek solutions.

The Guy in His 30s

Jamie Waters writes: I swam into the pandemic, still in my 20s, in a pool of oversize clothes. I tossed big knits over big T-shirts, billowy pants and bloated sneakers. I turned 30 during lockdown—blowing out candles in a park while dwarfed by an XXL paisley hoodie. In the ensuing months, I wondered: Had I outgrown my youthfully baggy wardrobe?

In my 20s, I embraced the graphic prints, bold logos and slouchy silhouettes dominating menswear. Now, like many of my fellow millennials, it was time for my style to mature. “There’s a difference between growing up and growing old,” said Jian DeLeon (pictured), Nordstrom’s men’s fashion and editorial director.

Roy Rochlin/Getty Images for IMG Fashion

Have fun but also go see a tailor, said Los Angeles stylist Chris Kim. Your 30s are when you “realize that fit is crucial.” To elevate your look, he advised getting a few key pieces custom fit.

Our millennial guy pairs the generation-spanning jeans (not shown) with a cable-knit fisherman’s sweater distinguished by texture not logos, and bright-but-not-bloated kicks.

The Man in His 60s

Vincent Boucher writes: If you’re over 50, your first reaction to the creep of casualization might be to retreat to your trusty suit. Traditional tailoring can be a safety net for older gents. But this 69-year-old believes there’s fun to be had by branching out.

Look at Brad Pitt, 58, who’s 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 one reporter asked why, Mr. Pitt said: “I don’t know! We’re all going to die, so let’s mess it up.” That’s as good a style credo as I can think of.

From left: Action Press/Zuma; Dominique Charriau/Getty

Many “upper-age” guys, New York stylist Jim Moore noted, wish to move past the quilted vests and chinos common among their peers. According to him, they’re saying, “I want to play in the new style sandbox.” Stylists recommend options like replacing a blazer with a statement shirt jacket or a Rick Owens high-top sneaker for an idiosyncratic touch.

Nixing formal tailoring, our older gent also uses sturdy jeans (not shown) as a base. He combines them with a laid-back suede jacket, a polo (less obvious than a button-down shirt) and unstuffy Chelsea boots.

Studio Photos by F. Martin Ramin/The Wall Street Journal; Studio Clothes Styling by Jill Telesnicki; Fashion Styling by Lizzy Wholley; Grooming by Mirna Jose/See Management; Models Garrett Swann/Bella Agency; Bradley Evans/Bella Agency; Dogs Rugby and Wyatt/All Creatures Great & Small