Hailey Bieber and Kendall Jenner Test Fall 2025 Trends Worth Shopping

If Hailey Bieber and Kendall Jenner starred in a reboot of The Simple Life, I’d tune in religiously. The close friends already reunite regularly. Adding in some manual labor (you know, for the plot) would create a must-watch show. Imagine if Bieber and Jenner—who are currently in New York City together—gave their trip The Simple Life treatment. I wouldn’t have to wonder what they’re up to, because it’d be right there on TV.

For now, I’ll settle for the friends testing every fall 2025 trend within arm’s reach. After lunch on Wednesday, a Gen Z-er’s Paris Hilton and Nicole Richie were spotted around New York’s West Village. Bieber and Jenner matched each other’s energy—and the neighborhood’s classic-cool street style—in autumnal co-ords, each curated around elevated outerwear. First up: Bieber. A black leather jacket started the Rhode founder’s set, as it usually does. This time, she swapped an oversize bomber for a fitted blazer. She layered its patent exterior over a beige two-piece, featuring a crop top and a matching cardigan, both from La Ligne. It looked sleek alongside the flared trouser trend, which she regularly re-styles in NYC.

Bieber’s trusty socks-with-loafers hack peeked out beneath each fanned hem. Knowing the supermodel, the slip-ons hail from The Row, but not the brand’s sample sale. She’s owned the three-figure flats for years.

Hailey Bieber and Kendall Jenner were spotted in New York together wearing complementary fall outfits — Hailey Bieber and Kendall Jenner took New York in luxe off-duty looks.

I wouldn’t be shocked if their outing was an undercover The Row campaign. Bieber and Jenner’s looks were cut from the same cloth. Jenner’s straight-leg jeans proved she got the off-duty model memo—similar styles from Prada, Isabel Marant, and Khaite had a moment on Fall 2025 runways. Their dark wash appeared to channel one of Bieber’s favorite trends right now: indigo denim.

Jenner paired the jeans with a black pea coat, which stopped a full two feet shorter than her The Row Harri Coat the day prior. It matched her wool-blend bucket hat, also from the Olsen twin-led label. She countered Bieber’s loafers with patent leather ballet flats.

A bright blue scarf, which draped long past her knees, felt ahead of today’s trends. Lookalike shades debuted in Spring 2026 shows from Jean Paul Gaultier, Valentino, Akris, Lacoste, and Victoria Beckham (to name a few).

Hailey Bieber and Kendall Jenner were spotted in New York together wearing complementary fall outfits

A moment for Kendall’s set, which was slightly more vibrant than Hailey’s.

(Image credit: Backgrid)

A The Simple Life reboot may be a fever dream. But more street style serves from Bieber and Jenner certainly aren’t. In fact, the duo might deliver a season’s worth of outfit inspiration before the week’s done. They’ve done it before, who’s to say they won’t do it again?