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.
Vogue’s Favorite ‘90s Loafers:
The Spotted Slippers
Reformation x Alexa Chung Pony slippers
Jump to reviewThe Heeled Penny Loafer
Jamie Haller The Heeled penny loafers
Jump to review
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.
