Hailey Bieber Pairs Her Vintage Gucci Dress With a Divisive Modern Shoe
It was a styling choice only the beauty mogul could get away with.


Hailey Bieber’s dress has some major fashion history, but her shoes are totally modern. In New York City yesterday, the model showed that she knows her fashion history by wearing a look that blended two distinct decades.
Bieber donned a fitted dress from Tom Ford’s spring 1998 collection for Gucci. But this wasn’t like the usual va-va-voom Ford-era Gucci designs that Bieber typically favors. It was created in a light shade of Tiffany blue and featured a demure boat neck silhouette—more Swan of Fifth Avenue, less Downtown Siren.
The model, never one to stay behind on the trends, updated her vintage find with a pair of controversial clear heels from Gianvito Rossi. While Bieber has a vast collection of archival garments, her unexpected footwear choice added something new to the Gucci dress. And, considering who has worn the same piece in the past, Bieber’s styling trick came in handy.
Bieber’s dress caught the eye of Vogue editor Anna Wintour after it debuted during Milan Fashion Week in 1998. Wintour donned the piece to the 1998 CFDA Awards, which she attended with the late André Leon Talley, who also wore his own Ford-designed Gucci look. The design was also featured in Vogue’s March 1998 issue in a Steven Meisel-photographed fashion spread. A longer version of the dress even made its way onto Helen Hunt at the 1998 Academy Awards. She took home Best Actress that night for As Good As It Gets.
Like a true vintage connoisseur, Bieber was aware of her dress’s famous back story. The Rhode mogul re-posted an Instagram story shared by her stylist, Dani Michelle, with the words “Icons only” written over the image of Wintour and Talley.
Stars galore are descending upon New York ahead of Monday’s Met Gala. (Bieber’s pal, Kendall Jenner, also arrived in the Big Apple yesterday.) And while Bieber could be simply enjoying some time in the city or tending to her beauty business, there’s a strong chance she’s ready to return to the Met for the first time since 2022.
Perhaps, her vintage dress (mainly the Wintour connection) is some signal that she’s sent in her RSVP for fashion’s night out.