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On Fashion: Fashion Mistakes Are Cringe-Worthy Learning Chances

The year: 1987. My outfit: A pin-striped pink jumpsuit with cropped legs and a sort of Oompa Loompa-uniform bagginess. In the photo my mom snapped of me wearing it, teenage Jenn looks delighted and confident. But today, I cringe at both the clothes and my puffy, permed hair — was it styled by a pack of squirrels?

Many of us suffer from sartorial repentance, an after-the-fact realization that we were wearing the wrong thing or sporting a hairdo only attractive on a Pixar monster.

Often such regrets stem from falling for ill-advised, unflattering trends — 1970s leisure suits, 1990s overalls, neon anything ever — that only seem terrible in hindsight.

“I recently saw a photo of myself at age 14, and I had this horrible wedge haircut,” says Silver Spring, Md., personal shopper Rosana Vollmerhausen. “It was really unflattering, but at the time, I thought it was amazing.”

Eliot Payne, one of the Washington-based designers behind the about-to-launch suit company Paul Eliot, shudders when he remembers his college wardrobe.

“I wore all kind of strange pants — sweats, pajama bottoms — to class, thinking it was cool to do just what I wanted,” he says laughing. “And later, I had a visor with my fraternity’s initials on it. It was so bro-y.”

Looking back in horror comes, in part, from the fickle nature of fashion.

“It’s just a natural part of styles coming in and out,” says Linda Przybyszewski, an associate professor of history at the University of Notre Dame and author of the upcoming The Lost Art of Dress: The Women Who Once Made America Stylish ($21, Basic Books). “We’re all complicit.”

Plus, today’s rapidly coming and going trends — camo-print jeans this week, plaid stilettos the next — are aimed at tweens and teens, “And they love novelty,” Przybyszewski says. “They’ll buy things just because they’re new.”

Still, if you’ve passed Lorde’s age, this might mean pausing before indulging in Forever 21’s latest hit. Having a good time with your wardrobe is OK, but looking like a fashion victim tomorrow on Facebook (or for eternity in your cousin’s wedding photo) isn’t.

As your sense of style matures, your missteps become less frequent.

“Dressing well has to do with your taste level,” Payne says. “When you first try your hand at it, you suck at it.”

And the old adage about investing in classics — a black sheath for girls, a trim gray suit for dudes — is worth considering. After all, Audrey Hepburn and Cary Grant never had a bad clothes day.

“Many pieces from the past look beautiful,” says Betsy Fisher, owner of the Washington boutique by the same name. “Tailored things can be timeless. It’s when you go for silk parachute pants that you lose it.”

Still, even fashion pros like Fisher cop to regrettable closet moments.

“In the 1980s, I had a Norma Kamali black, red and white skirt. It looked like she designed it for Snow White in a Disney movie.”

Well, at least Instagram wasn’t around then — or when I was rocking that jumpsuit.

How to know if today’s faux hawk is tomorrow’s beehive?

∎ “You’ll regret anything that makes you look sloppy,” Vollmerhausen says. “I definitely think that applies to boyfriend jeans!”

∎ Clothes that make you uncomfortable or that endanger your health won’t stand the test of time.

“The most famous fashion regret was the hobble skirt: a narrow, past-the-knee style around 1910,” Przybyszewski says. “They restricted movement so much that one woman drowned while wearing one.”

∎ Don’t take it too seriously. “Fashion locates you in a time and place, “ says Fisher. “Don’t worry so much about how a dress will look in a photo in 10 years.”