Kaia Gerber is used to showing us how to dress, whether she is on the runway or making a red carpet appearance. But recently, the model showed that her style is just as worth noting when she is out on the streets. Gerber was seen casually walking through New York City with her phone and earphones on, wearing an off-duty look that still brought in a few of the pieces currently trending.

Photo: Backgrid

She stepped out in a blue “Spoiled Boys” T-shirt from New York designer Emily Dawn Long, featuring an off-the-shoulder neckline on one side and a cropped fit. She paired the top with a low-rise black skirt that fell below her knees, leaving a small part of her midriff visible.

She also leaned into the ballet flats trend, wearing a pair that kept the outfit comfortable The model finished the look with dark sunglasses and a small animal-print bag with a leather strap. Her hair was worn in loose, wavy strands, adding to the laid-back feel of the outfit.

Photo: Backgrid

The “Spoiled Boys” T-shirt has also been seen on other celebrities, including Pedro Pascal, Paul W. Downs and Tommy Dorfman. Emily Dawn Long first introduced the design earlier this year, using vintage T-shirts as the base and adding the “Spoiled Boys” print across them. Since then, the designer has released the style in different colors and versions.

Photo: Backgrid

The New York outing came during a busy week for Gerber. Just a day earlier, she attended the U.S. Open, where she was seen alongside her The Shards co-star Homer Gere. She and Gere are also the stars of Vogue’s September 2026 issue, and the pair recently visited Casa Magazines in New York to celebrate the cover.

Rihanna is making a case for one of the most recognisable outfit combinations of the 2000s: a sporty zip-up jacket worn with a tiny denim skirt and heels.

The singer and Fenty Beauty founder was photographed in New York on 21 August while out with A$AP Rocky and their children. She wore a candy-pink Miu Miu track jacket with a dark-wash denim mini skirt by Meryll Rogge, bringing together two staples strongly associated with early-2000s dressing.

The Miu Miu jacket has a cropped fit, ribbed cuffs and hem, and contrasting cream stripes running along the sleeves. Rihanna wore it zipped most of the way up, with the collar turned up and her hands tucked into the pockets. The soft pink shade is also familiar territory for the era, recalling the pastel tracksuits and baby tees that were everywhere in the early 2000s.

Photo: Getty Images

The denim mini skirt gives the outfit its strongest Y2K reference. Its dark wash, low-rise cut and frayed edges are deliberately reminiscent of the decade, while the exposed white pocket linings add another detail to the otherwise simple denim piece. The skirt’s uneven hem, with a longer section falling at the front, keeps it from looking like a straightforward vintage throwback.

Then there are the shoes. Instead of trainers or flat sandals, Rihanna chose strappy snakeskin heels by Amina Muaddi. It is a small but important styling decision: the track jacket could easily have pushed the outfit towards casual sportswear, but the heels take it in a more dressed-up direction.

Her accessories continue the reference. She wore oversized rose-tinted aviator sunglasses, large hoop earrings and a broad gold choker, while carrying a black quilted bag. The jewellery and sunglasses are particularly suited to the outfit because they echo the larger accessories that were central to celebrity style at the time.

Rihanna kept the beauty look equally recognisable. Her hair was worn in voluminous curls, paired with a glossy brown lip and a deep red manicure. A white pedicure was visible beneath the open-toe heels.

The look also arrives during a week in which Rihanna has repeatedly returned to early-2000s fashion. Just days earlier, she wore a burnt-orange Chloé velour tracksuit for dinner in New York, complete with snakeskin sandals, oversized sunglasses and gold jewellery.

Photo: Getty Images

What makes this latest outfit worth noting is the way the pieces are mixed. The jacket is sporty, the skirt is deliberately tiny and distressed, and the heels belong to a completely different part of the wardrobe. Nothing is trying to make the outfit look like a perfectly matched set.

That approach is particularly relevant to the current return of 2000s fashion. Instead of bringing back every element of the decade at once, Rihanna has taken a familiar formula and adjusted it through proportion and accessories. The result is recognisably Y2K without relying on a head-to-toe recreation.

For anyone who remembers the original era, the combination will be immediately familiar. For those discovering the trend for the first time, Rihanna’s version offers a clear lesson in how to update it: keep the sporty jacket, bring back the mini skirt and let the shoes and accessories change the mood.