My Friend’s Style is Becoming Embarrassing. Should I Tell Her?

The unfortunate truth is that one person’s embarrassing or provocative style is another person’s iconic look. Think of such individuals as Diana Vreeland with her Kabuki makeup, or Iris Apfel with her ginormous glasses and armfuls of bracelets, or André Leon Talley with his flowing capes and caftans and, yes, towering hats. Which often blocked the views of the people behind him — and for whom he never batted an eye.

Often it is the most extreme and idiosyncratic among us who are the most remembered for their looks. “Taste” can be a synonym for forgettable, and dress codes are meant in part to make everyone the same.

As Arianne Phillips, the stylist and costume designer of (most recently) “Don’t Worry Darling,” said, “The wonderful thing about dressing is it gives us the ability to communicate and express who we are, who we want to be, and sometimes what we believe in.”

And that can make other people uncomfortable. Most of us are taught to avoid calling attention to ourselves. There is a human imperative to fit in and signify yourself as part of a group, often by dressing like that group. Whether the “dress code” involved is official or not. So when someone, like your friend, chooses to step outside the fashion norms, it can seem like a threat to the social contract.

Even if it’s just the social contract of after-hours partying.

On the other hand, dress codes can also be used as a means of control, and transgressing them can be a statement of change. (See what is currently happening with women in Iran.)

In the case of your friend, that means understanding why she is dressing the way she is dressing — and why you find it disturbing — is key.

“I would strongly suggest the best way forward is to privately have a conversation with them,” Ms. Phillips said. “Perhaps there is something else afoot that a loving conversation will illuminate.”

Maybe your friend’s fashion experiments are an expression of a deeper, more intense shift in her identity, in which case her need for your support may trump your own unease. Or maybe it’s just a lark. Maybe your discomfort says as much about your own expectations and social conditioning as it does about her.

Either way, this is probably a situation in which, as Cameron Silver, the owner of vintage destination store Decades and a noted clotheshorse, said regarding dress codes and public places such as restaurants and bars, “Let the management of the business handle the issue,” the better to preserve your friendship.

And maybe, when your friend looks really kooky, as Mr. Silver said, ask yourself: “What would Bill Cunningham do?” If the answer is “snap their photo so your friend would end up in The New York Times Style section,” perhaps you should just go with the look. Even if everyone else stares.

Every week on Open Thread, Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or Twitter. Questions are edited and condensed.

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