Grace Kelly and Audrey Hepburn Are the Unlikely Style Icons of the Downtown Fashion Set

While the NYC downtown set might be most frequently associated with the restaurant you’ve never heard of and the daring new fashion trend that hasn’t even hit TikTok yet, there has been a surprising wave of nostalgia hitting the cool style set recently. Instead of low-slung jeans and Sambas, downtown looks more often resemble those of Grace Kelly and Audrey Hepburn—style icons who are the pinnacle of elegant fashion from the 1950s and 1960s and helped popularize pieces such as pillbox hats, skirt suits, animal-print outerwear, and pumps.

It was polished dressing and sophisticated style at its height, which is perhaps why it’s so surprising to see it adopted by the downtown fashion set. Maybe that is what makes it feel so right. It is a 180-degree turn away from the edgier fashion we’ve come to associate with anyone living in lower Manhattan, which makes it unexpected yet exciting and fresh. Ahead, see more on the nostalgic style that is defining how the fashion set is dressing.

Pillbox Hats

Pillbox hats are practically an essential for the fashion set at this point, whether in white sculptural felt or leopard print. The accessory was a staple of Audrey Hepburn in the 1963 film Charade but is equally likely to pop up on the 2025 street style set.

TOTEME

Shearling Pillbox Hat

Car Coats

The classic trench is getting an elegant and sophisticated twist with the car coats popping up everywhere. Style insiders are pairing the knee-length, single-breasted outerwear with slip skirts and sleek pumps.

Leather Gloves

A key outfit finisher for the final month of winter? Leather gloves. They are often styled with a tailored skirt suit or car coat, as frequently seen on Grace Kelly in the 1950s and 1960s.

A-Line Silhouettes

Flared A-line silhouettes have been gaining popularity in recent seasons and are going full steam ahead for this coming year. Whether in coat, skirt, or dress form, the fluted shape feels like a throwback to the style of previous decades.

Top-Handle Bags

Pocketbooks, doctor bags, carryalls, and more finished with top handles are the bags of choice at the moment. Many of the polished bags have a vintage-meets-modern feel.