Samantha Gregory, vice president of global communications for Tory Burch, takes a similarly streamlined approach, giving her workweek Christian Louboutins a rest in favor of Tod’s driving shoes, along with Tory Burch cardigans and tunics, J. Crew corduroys, and Steven Alan and A.P.C. shirts. “I think that Sex and the City ruined people’s notion of weekend casual. People saw that show and thought that you were supposed to wear cocktail dresses on the weekends,” muses Gregory. “I think it’s odd when I see four girls out having brunch in wrap dresses and heels.” Indeed, it is those who insist on hobbling their way through errands in the latest Givenchy platforms who give one pause: Trying too hard is never a good look.
Gregory has a kindred spirit in Eleanor Ylvisaker, who, thanks to her position as public relations director and partner of Earnest Sewn jeans, has perfected the art of 24-7 denim dressing. Though she may don a Carolina Herrera or Chanel frock for a high-end affair, her typical nine-to-five ensemble consists of fitted dark jeans with heels and a “nicer top.” Downgrading for weekends in her SoHo hood is as simple as switching to a lighter wash and more relaxed cut, paired with Balenciaga and Loro Piana knits, tank tops by The Row, and Repetto flats or Loeffler Randall boots. And Ylvisaker doesn’t sweat maintaining a stylish demeanor, even after clocking out. “I really like fashion, and I like being creative with my clothing, so to me it doesn’t feel like pressure,” she says.
Yet for all the talk of relaxed, easy attire, there are certain items considered verboten on even the most casual of days. “Definitely never sweatpants and sneakers unless I’m going to the gym,” says Kate Etter, public relations manager for Nina Ricci, who trades towering Pierre Hardys for black Chanel flats during her Lower East Side errand runs.
“French people don’t really ‘underdress’ on the weekends.…[The gym] is the only time I would wear sneakers,” agrees Chelsea resident and art director Julia Restoin Roitfeld.
“I don’t really do the Ugg thing,” Ylvisaker adds of the still ubiquitous winter footwear.
Throw a zip code change into the mix, and the casual-chic ante can rise and fall with the corresponding real-estate prices. “I definitely think the Lower East Side allows you to be more hip and fun. It might be easier to get away with a more pared-down look there than, say, the Upper East Side,” Etter says.
Gregory is all too familiar with the neighborhood effect on shifting clothing patterns. She divides her time among eternally laid-back Los Angeles (where husband Roberto Benabib works); über low-key Washington, Connecticut, where she keeps a country house; and Manhattan’s relaxed-but-hip West Village—with the occasional foray uptown to 10021 land.