Hailey Bieber Takes Style Notes From Anna Wintour in a 1998 Gucci by Tom Ford Mini Dress

Hailey Bieber gets her style inspiration from the best in the business.

Bieber, 28, stepped out in a Tiffany blue Gucci by Tom Ford vintage mini dress — once worn by the inimitable Anna Wintour — while out and about in New York City on Wednesday, April 30.

The frock featured a square neckline, a sleeveless design and a fitted silhouette. She paired the look with black oval sunglasses and nude Gianvito Rossi pumps, then finished it off with a clutch from The Row.

For glam, Bieber donned a full beat including bronzy eyeshadow blended into her crease and glitter pigment on her lids. She completed her makeup with rosy cheeks and pink lips. Her caramel brown hair was parted down the middle and styled in a shiny blowout.

Beiber’s stylist, Dani Michelle, took to Instagram to show off her client’s look, which was inspired by the “icon” Wintour, 75. The Vogue editor-in-chief originally wore the 1998 look at the US Embassy cocktail party in Paris that year, alongside the late Vogue editor-at-large André Leon Talley.

andré leon talley and anna wintour both wearing gucci by tom ford s/s 1998 (with wintour in a blue variant of the runway look) at the U.S. embassy cocktail party in paris, photographed by angelica blechschmidt (1998) pic.twitter.com/OphMpbMXa5

— Nathan (@muglerize) December 14, 2021

At the time, she styled it with a bright red pout and her signature bob.

The Rhode founder later reposted the throwback photo of Wintour on her Instagram Story along with pics of herself posing in the outfit.

This isn’t the first time Bieber has slayed in a vintage look. In December 2024, she wore a 1996 Versace brown skirt, paired with a matching blazer.

To make her office siren look even more glamorous, Bieber elevated her look with a bedazzled “B” necklace. In true cool mom style, she completed her getup with black shades, which, of course, is perhaps Wintour’s most famous signature of all time.