“My husband and I went to have an Upper East Side day and we were like, ‘What are we gonna wear?’” Gregory recalls. “I remember feeling like I had to brush my hair and look a lot nicer because everyone’s decked there.” It’s certainly a 180 from her time spent in the country. “There’s a coffee shop we go to every morning, and once in a while we’ll run into someone and I’m like, Oh, my God, I can’t believe I’m basically wearing my pajamas,” she says. “But everybody looks like that there.”
That may be true in comfy Connecticut, where fellow fashion toilers are few and far between. Alas, the same cannot be said for the concrete jungle, where weekend industry run-ins are common. Leaving the house in a less-than-presentable outfit can become increasingly perilous with the rising fashion gal–to–civilian ratio. While the Upper East Side may necessitate only a hairbrush and a clean-lined blazer, Chelsea and its stylish cohorts require a more artful approach. Should the inevitable encounter occur, it seems a girl’s best armor is a que sera, sera attitude.
“I don’t find it a pressure to always be ‘ready to run into people.’ We all go to the gym at some point!” Restoin Roitfeld says. “Your look is very important in this industry, but dressing up is for my own pleasure, during the week or on weekends.”
Ronson concurs. The designer—who on off days turns to her own cool-girl, albeit artfully disheveled, pieces like cardigans and plaid shirts, as well as distressed Current/Elliott jeans and Alexander Wang tank tops and T’s—says “Bring it” to anyone who criticizes her wardrobe choices. “If someone’s going to judge me, please, that would be kind of fun,” she says with a laugh. “I’d love to hear why.”