Black loafers were one of the most popular shoes in the ’90s thanks to their minimalist, classic and timeless design.
Less was more during this decade, and designers like Calvin Klein, Tom Ford and Helmut Lang were some of the pioneers in seeing the beauty behind simple pieces like slip dresses, monochromatic suits and androgynous tailoring.
Thus, the likes of Sarah Jessica Parker, Cameron Diaz and Carolyn Bessette Kennedy opted for no-fuss footwear as a way to finish their outfits with an elegant, comfortable look that matched with everything, no matter the occasion.
READ MORE: The best loafers for women.
In the ’90s fashion, versatile items were the most valued. This is what made black loafers a must-have. Sarah Jessica Parker, just like Carolina Herrera, preferred hers with a square heel, which gave a more formal look. While the Venezuelan designer wore hers with dress pants and a turtleneck sweater, the actress opted for a white shirt and a pencil skirt in 1990.
Cameron Diaz was another celebrity who couldn’t resist loafers. And although the red, square-toed pair she wore on a date with Jim Carrey has its own fan club, this time we’re focusing on this relaxed midi skirt look she wore with a white T-shirt, a sweater tied at the waist and, of course, black loafers. The style icons of this decade opted for a casual, minimal sensibility, which was perfectly achieved with this footwear.
And speaking of casual attire, Carolyn Bessette Kennedy became a benchmark in this department. Having been a publicist for Calvin Klein, she took lessons from the American house firsthand and became an expert in wearing black loafers with jeans. She paired her favourite bootcut styles with trenches and long coats to add a low-key air to halter tops and dresses while walking around New York.
Recent catwalks were an ode to the ’90s, with brands like Givenchy, Miu Miu and Anteprima presenting black loafers as the final touch to their looks, placing them firmly as one of the trending shoe styles for autumn/winter 2025.
So, how to style loafers the best way? The minimalist design is the first thing to take into account. With its almond toe and low sole, this black design is a classic that can be worn with satin or lingerie-style dresses to create a contrast between sensuality and formal style. Finish it with sheer tights and a cardigan.
On the other hand, those black patent loafers are ideal to wear with flared jeans and long sleeve bow blouses for a distinguished but relaxed look. If you want to go all the way, go for a red leather blazer.
And for those days when you want to be comfortable without giving up style, we suggest black loafers with square heels. Match them with corduroy trousers, a striped shirt, a sweater vest and a short coat.
A version of this article was originally published on Vogue Mexico and Latin America.