Has Bostonians’ addiction to casual dressing gone too far?

We were way ahead of the hugely popular athleisure trend. But there’s a right and a wrong way to wear it.

Pascal Campion

Bostonians have never been that keen on trends, at least not while they’re actually trendy. Recall the Ugg phenomenon, which hit town in earnest precisely as the rest of the world was starting to ship theirs off to Goodwill. Or skinny jeans, which many of you boot-cut loyalists around here still refuse to wear. It would be hard to argue, though, that Bostonians weren’t hip to the athleisure ethos long before the fashion world’s latest obsession had an actual name. We’ve been dressing for comfort for years.

Athleisure, an amalgam of athletic and casual wear, is fashion’s hottest and most profitable trend, with national revenues hovering around the $35 billion mark. It’s the all-day, head-to-toe sporty look that says you’re just coming from your absurdly overpriced boutique fitness class or you’re heading there, even if you never actually generate a bead of sweat (the accompanying hair, curiously, is usually salon-perfect). It’s less about wearing clothes for the gym than clothes that look as though they could be for the gym. If you’ve spent any time in a Whole Foods/Starbucks/school drop-off zone in a suburb west of Boston, for example, you’re familiar with this way of dressing.

Part of the appeal is, obviously, ease: If all your yoga pants are black, who can tell if you’re wearing the same ones as yesterday? Yoga pants don’t chastise you for last night’s third glass of wine while at the same time they convey that you’re a multitasker with healthy priorities in a way your jeans and T-shirt never really could. There’s also a functionality to all-day leisurewear that speaks to Bostonians’ pragmatism — although we’ve become both more adventurous and more willing to spend on fashion in recent years, we still like getting as much wear as we can out of our clothes.

“Boston is a very practical market,” says Tina Burgos, a local retail veteran who ran Newbury Street boutique Stel’s before opening e-commerce shop Covet + Lou, which stocks clothes that skew casual, if not actual athletic wear. “More than New York or LA, here we’re spending on real estate, restaurants, vacations, kids. Fashion really has to be incorporated into someone’s lifestyle in order for it to work. Women don’t want, or have time, to think about it too much. They want to be able to throw it in the washing machine.” Compared with her shoppers in other parts of the country, Bostonians like clean, minimal, conservative. “If something really works here, they say, ‘It’s so comfortable’ or ‘That material’s so great, and I can run around in it in 90-degree weather and then wear it out to dinner,’ ” she says. “It always comes back to the functional aspect.”

Though Bostonians like to look good, we like it to look effortless even more. We don’t want anyone to think we’re trying too hard or spending too much. “It’s a very New England thing,” says Burgos. And, to be fair, we often are just back from or en route to the gym, as evidenced by the fact that we rank in the top 10 in surveys of the country’s fittest cities.

There’s still an art to this way of dressing, however. Recent activewear launches and collaborations from such high-end designers as Rick Owens, Alexander Wang, and Raf Simons as well as local launches from brands like Crane & Lion and Wellesley-based Tracksmith make it easy to abandon the actual yoga outfit in favor of something a little more dressed up but just as versatile: silk pants with elastic cuffs, cashmere hoodies, limited-edition running shoes you’d never dare run in. Still, this is a trend that very much began, as the best ones do, with the people: a natural evolution of day-to-night dressing, which had designers coming up with solutions for working women who wanted to be able to transition from the office to dinner out. These days, we’re even more on the go.

Which raises the question: When will it be OK to show up at the office in sweatpants? Probably pretty soon. “Years ago, you couldn’t wear jeans to work; they were too casual or too sloppy,” says Burgos. “Now, even some of the most serious of industries allow jeans. I have professor and doctor clients who wear denim to work. My husband works in corporate banking. He wears jeans every Friday.” That’s, of course, because women started spending $250 on designer denim and demanded to put it to use. But there are also the growing ranks of independent contractors to consider — as someone who works from home most days, I now have six pairs of Vans slip-ons where my “work heels” used to be — not to mention the state’s 300,000-job strong millennial-stocked tech sector.

“Unless you’re in a very serious high-level corporate job environment, I think suiting is a thing of the past,” says Burgos. Bostonians might like conservative, but we don’t like inflexible. “With athleisure, you can really live this way 24/7 with very minor adjustments,” she says. “It’s all how you put it together.”

The putting-it-together part is key. Athleisure is not the fashion world giving you permission to underdress. “I think it’s a fantastic thing that people are exercising, but the all-day running-tights/yoga-top look is just another example of taking something and way overdoing it,” says Alan Bilzerian of the long-running eponymous Newbury Street boutique. “In America, there’s no in between, no right time for everything, not anymore. When casual Friday started, bad dressing all week long was the next course of action. We’ve lost knowing how to present ourselves.”

Successful sweatshirt dressing doesn’t mean wearing your old college standby out to dinner or pretending your pajamas are high fashion. “A big part of what I am doing is working with women to bring in sporty, comfortable pieces while escaping from the all-Lululemon all-day look,” says Kerry Epstein, a Boston-based personal shopper and stylist. “To implement it right, it’s similar to high/low dressing. Pair a sneaker with a skirt. Or a fitted sweatshirt with a wide-leg pant or jean. My favorite personal outfit right now is an Isabel Marant black sneaker paired with a leather — in my case faux — pleated skirt and a simple white tank.” Do not, she says, wear head-to-toe workout clothes.

Unless, of course, you’re actually working out.