Sure, I Have Fashion Regrets. All the Best People Do. – New York Times

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 the wellness 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.

“You have so much going on there,” he said. My contract as a contributing editor was terminated soon after that.

But is obliviousness so wrong, especially in a world where so many are so stuck on getting it just right? Isn’t there something to be said for making yourself vulnerable enough to allow others who are more insecure to feel superior? And aren’t we all secretly grateful for a sense of fun, however misguided, even if it clashes with the dress code, and the wallpaper?

“I’ve worn all kinds of crazy outfits, and I don’t regret any of them,” Mr. Posen told me. “You have to take risks, that’s what makes New Yorkers so special. It’s all about invention!”

As for Bjork’s swan dress, made by Marjan Pejoski, a Macedonian, it had the last laugh and the last honk. Valentino reimagined it for the spring 2014 couture collection, and the next year it made it into the Museum of Modern Art. My Guatemalan tapestry jeans? They’re in a book. Je ne regrette rien.

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