CBK Lovers, Take Note: The ’90s Heeled Loafer Is Making a Comeback

There’s a photo of Carolyn Bessette-Kennedy and John F. Kennedy Jr. leaving the Bowery Bar in October of 1995—it’s blurry and grainy and because of it, one of CBK’s lesser known style references. Still, it lives in my mind for a particular reason: her shoes. In the image, she’s wearing a white button-down and cropped, flared jeans with a pair of Prada 1995 heeled Dalmatian print loafers. It’s this exact photograph that sparked in me an early fascination with Bessette-Kennedy’s footwear, and prompted a year-long hunt to source the rare shoe styles she wore in the nineties. I’ve yet to uncover this specific animal-printed pair on the secondhand market (rest assured, my notifications are set); I’d argue it might be one of her hardest to track down.

The spotted print first appeared on Prada’s fall 1995 runway in heeled mule form (later seen on Kate Moss in the summer of 1996). While Bessette-Kennedy’s heeled loafers are my white whale, the silhouette feels just as relevant today. To wit: Earlier this fall, Prada reissued its coveted Dalmatian print loafers; elsewhere Herbert Levine, Dries Van Noten, and Phoebe Philo all offered their own interpretations of the shoe trend for the season.

For me, part of the heeled loafer’s appeal in the ’90s was the balance it struck between masculine and feminine dressing—the substantial upper of a traditional loafer lifted by a heel. From Kate Moss at the airport to Gwyneth Paltrow on the red carpet, the shoe earned its reputation as one of the most versatile styles of the decade—a sentiment that still rings true. Worn with jeans and a white tee, or a slouchy knit and tailored trouser, the heeled loafer possesses just enough structure and height to balance casual day wear with a touch of sophistication.

While I remain on the hunt for an elusive original Prada, these are the current styles that I’d invest in, each getting something right about the heeled ’90s loafer.

The Printed Loafer

While most of us equate the fashion in the ’90s as minimalist, some of the decade’s boldest prints appeared on its shoes. The printed loafer came into its own in those years, when Miuccia Prada and Tom Ford at Gucci invigorated the traditionally staid shape, turning out punchy options in brightly colored snakeskin and animal print pony hair. Prada’s 1995 spotted loafer is one of my favorite examples, and the modern reissue possesses all the charm of the original. (Keep an eye out for Dries’s SS27 collection—which was filled with bold printed pairs.) When styling this kind of shoe, I like to keep the rest of my look simple, letting a glimpse of the pattern peek out from beneath a pair of worn-in Levi’s or even a black tailored trouser.

The Loafer Mule

A more casual take on the heeled loafer is the mule—seen in the mid-nineties on the runways, on the red carpet, and even at the airport. With Saint Laurent and JW Anderson among the brands revisiting the shape today, I’d take my styling cue from Moss and play up a punchy pattern with a white Leset tee and some cropped High Sport trousers.

The Minimalist Loafer

Among the heeled loafers that took off in the ’90s, the minimalist version had a distinctly off-duty ease. From the Row’s modern shape, to sharp takes by Khaite, the minimalist loafer is equal parts understated and refined. I am perpetually on the hunt for a loafer that I can wear with anything from a good jean to a slip dress, and this is exactly that. In colder months, I look for pairs with a little give to their leather so there’s room for a thicker sock.

Shop More: