Fearlessness, I suppose, breeds cluelessness. Or is it the other way around? In fashion as in life, isnât it often the regrettable that makes us memorable?
âDressing is always a learning experience, so you have to take risks,â 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 itâs âcheap and not well tailored.â
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.
âEvery time I wear it, itâs a conversation piece,â she said. âSo why not?â
Because sometimes wearing a conversation piece can be like wearing a âkick meâ sign, thatâs why. I know a cheeky woman who was a shoo-in for an advertising job until she wore a leather jacket â with the word âwildâ painted on both sleeves â 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.
âYou have so much going on there,â 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? Isnât there something to be said for making yourself vulnerable enough to allow others who are more insecure to feel superior? And arenât we all secretly grateful for a sense of fun, however misguided, even if it clashes with the dress code, and the wallpaper?
âIâve worn all kinds of crazy outfits, and I donât regret any of them,â Mr. Posen told me. âYou have to take risks, thatâs what makes New Yorkers so special. Itâs all about invention!â
As for Bjorkâs 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? Theyâre in a book. Je ne regrette rien.