Hailey Bieber Keeps Proving Her Favorite Black Loafers Are Worth the Investment

Ever since Simone Bellotti became Jil Sander's creative director in March, the Italian label has dominated every fashion girl’s closet. Jennifer Lawrence, Dua Lipa, and Hailey Bieber have all sourced its catalog multiple times in the past two months. But Bieber isn't a bandwagon fan. She's a longtime Jil Sander loyalist who first sported the brand's black loafers in March 2022 and hasn't looked back. On May 27, her favorite square-toe style by the designer still seemed good as new.

Yesterday, the new mom wore her Jil Sander loafers for the umpteenth occasion while out in L.A. The paparazzi captured Bieber exiting a meeting with United Talent Agency, modeling her tried-and-trues beneath a pair of slouchy black trousers. At first glance, you might've confused them with another The Row pair, but the recognizable wrinkles on each toe confirmed they were indeed her Jil Sander staples.

From there, Bieber kept a monochromatic beat with an oversized leather jacket from Saint Laurent. The devout brand ambassador used her moto topper to hide her shirt underneath. Knowing Bieber, she probably chose a white tee from LESET—another of her favorite off-duty brands.

Bieber is currently partial to Jil Sander's flattest loafers, but she's owned other options. Her first pair debuted during Paris Fashion Week in March 2022: a style with a harsher square-toe silhouette and thick, menswear-inspired soles. All eyes went to the supermodel's shoes at the time, but her leather Balenciaga trench coat, cropped cardigan, and body chain from Jacquie Aiche were equally enviable.

Since then, similar shoes have become a mainstay in Bieber’s daily rotation. She’s worn luxe Jil Sander loafers at concerts, on vacation in Japan, and for various date nights with her husband, Justin. They even proved to be pregnancy-friendly last year. At a Billie Eilish concert in May 2024, Bieber accessorized her footwear with chunky socks, which dressed up her laidback maternity look.

After more than 30 re-wears, most shoes would need a little TLC before returning to the style scene. Perhaps even a re-purchase. But not these. The more Hailey Bieber wears her Jil Sander loafers, the more she proves they're worth the investment.