Since the '90s, the Chicest Women Have Worn This Shoe Trend With Cropped Black Trousers

By Swedan MargenJuly 26, 2025

Few outfit formulas have the staying power of cropped black trousers and minimal loafers—and thanks to new images from the set of American Love Story, I've been reminded of exactly why this is. In recently released shots taken during filming, Sarah Pidgeon, who portrays Carolyn Bessette-Kennedy, one of the '90s most intriguing style icons, in the upcoming series, is seen in a quintessential look: black cropped trousers, a black roll-neck top and sleek black loafers, modelled off an outfit Bessette-Kennedy whilst out and about in New York in 1995. It’s ‘90s minimalism at its most elegant and yet, it couldn’t feel more relevant today.

Sarah Pidgeon in character as she portrays Carolyn Bessette-Kennedy in the upcoming series American Love Story, wearing black cropped trousers, black loafers and a black roll neck knit

Sarah Pidgeon films scenes for the upcoming series American Love Story, in which she plays Carolyn Bessette-Kennedy, an American fashion publicist and style icon also known for her marriage to John F. Kennedy Jr.

While the outfit might be rooted in CBK’s signature style, it’s one I still see fashion people wearing on a regular basis, and there’s a reason it endures. Personally, I think it comes down to balance. Ballet flats, though beloved and classy, can sometimes feel a little too delicate against a sharply tailored cropped trouser, especially one in a black tone. A loafer, on the other hand, brings the right amount of structure and weight. It grounds the outfit.

Carolyn Bessette-Kennedy (right) wears a navy jumper, black cropped trousers and black loafers in New York in 1995.

There’s also a certain polish that loafers inherently carry, especially when they’re pared-back in aesthetic. No chunky soles, no flashy details—just clean lines, soft leather and that subtle nod to classic style. Paired with black cropped trousers, the result is a look that's effortlessly smart and timeless; one that has transcended 30 years.

@fakerstrom wears a pair of black cropped trousers with a pair of black leather loafers and a taupe blazer

Whether you’re deliberately channelling Bessette-Kennedy or just looking for a fail-safe outfit that works for both city days and after-hours plans, this combination is hard to find fault with. Scroll on to see and shop my edit of the sleekest black cropped trousers and loafers on the market.