I Have Fashion Regrets

The turquoise and fuchsia weavings of the indigenous people of the Guatemalan village spoke to me. “Make us into a pair of jeans,” they said. I shouldn’t have listened, because the first night I wore them out in Manhattan those jeans made me look like a wall hanging.

We all have our fashion regrets, whether from overzealous sample-sale shopping or impulse buying at a market abroad. A new Rizzoli book, “I Actually Wore This: Clothes We Can’t Believe We Bought,” includes my regrettable jeans and the cringe-inducing garments of a runway of notables including Roz Chast, Yvonne Force Villareal, Molly Shannon, Chris Burch, Nick Wooster, Gary Shteyngart and Linda Fargo. It was written by Tom Coleman, with photography by Jerome Jakubiec.

Ms. Fargo, the Bergdorf Goodman creative doyenne with a new boutique that bears her name, models the Twizzler-red 3.1 Phillip Lim pantsuit she wore to a fashion event filled with people in black (the New York color of festivity), inspiring ungenerous texts and social media mockery.

“But I always like to scare myself a little,” she said at a party in the spring.

Hers is not the kind of boldface name, however, to attract universal scorn. While many dodged that bullet at the Metropolitan Museum’s Costume Institute Gala in May, with its avant-garde dress code in honor of Rei Kawakubo, years past have not been as kind to Sarah Jessica Parker or Rihanna, whose pooling yellow dress in 2015, a.k.a. the Omelet, was the equivalent of sartorial egg on the face.Other great moments of regrettable red-carpet display include the infamous derriere-showing Scaasi pantsuit Barbra Streisand wore for the 1969 Oscars and Bjork’s swan dress from 2001.

That girl should be put in an asylum,” Joan Rivers heckled.

“It’s just a dress,” the singer later responded.

But like a cigar, a dress is not always just a dress, especially in the political arena.

Ivanka Trump learned that when she posted a picture of herself and her husband, Jared Kushner, on Instagram on the January weekend when refugees were detained at airports because of her father’s ban on foreign visitors from seven Muslim countries. It didn’t help that her crinkly Carolina Herrera silver gown photo went viral when a detractor posted it next to a refugee girl in a blanket of similar material. In February, another social media outcry ensued when the first daughter wore a dress by French designer Roland Mouret to her father’s first congressional address — “Buy American” was a major theme — and some felt her bra-like black shoulder strap made the dress seem more Las Vegas than Congress.

In April, the flak jacket and blue blazer ensemble Mr. Kushner wore for a visit to Iraq provoked media sniping; it seemed more country club than conflict zone.

Of course, all this was minor after Kellyanne Conway’s showing on Inauguration Day. She called her much-mocked red, white and blue double breasted coat by Alessandro Michele of Gucci “Trump revolutionary wear.” Later she told The Hollywood Reporter she was “sorry to offend the black stretchpants women of America by wearing a little color on Inauguration Day.”

Fearlessness, I suppose, breeds cluelessness. Or is it the other way around? In fashion as in life, isn’t it often the regrettable that makes us memorable?

“Dressing is always a learning experience, so you have to take risks,” the designer Zac Posen said at a party not long ago for the latest novel by the Vogue contributor Plum Sykes. The only time Ms. Sykes regrets an outfit, she told me, is when it’s “cheap and not well tailored.”

Her sister Lucy, a stylist-turned-novelist who has most recently explored thewellness craze with Jo Piazza, her co-writer, was working the party in bright blue lipstick. She had no regrets even if it was drawing attention away from the guest of honor.

“Every time I wear it, it’s a conversation piece,” she said. “So why not?”

Because sometimes wearing a conversation piece can be like wearing a “kick me” sign, that’s why. I know a cheeky woman who was a shoo-in for an advertising job until she wore a leather jacket — with the word “wild” painted on both sleeves — to her final interview, in the 1990s. My own attempt to wear a radical mix of plaids during the grunge moment resulted in a disdainful once-over from the editor-in-chief of a magazine. He was in a dark, slim-cut suit.