Kendall Jenner Dresses Like a Preppy Ralph Lauren Muse in a Cherry Red Skirt, Navy Dad Hat, and The Row Loafers

Kendall Jenner takes a stylish trip to the bookstore in a new FWRD-sponsored photo dump shared to the model's Instagram. Although the 29-year-old generally strives to emulate Carolyn Bessette-Kennedy with her street style, I couldn't help but see a couple more references in her color-blocked ensemble.

The combination of her cherry red knee-length skirt and oversized black cashmere crewneck sweater instantly reminded me of vintage J.Crew catalog styling. Ditto for her navy blue Polo Ralph Lauren baseball cap, which matched the hue of her midi skirt to the brand's cherry-red embroidered logo hovering above the bill. These days, It girls like Kaia Gerber and Zoë Kravitz love to let their status symbol dad hats do the talking.

Her black loafers and white socks, on the other hand, sent me hurtling back to the preppy, heritage brand-centric ensembles of the lads who populated my high school's lacrosse team. Their loafer outfits usually paired the shoe with Nike athletic socks and colorful elastic shorts. But I personally prefer Jenner's riff on the boyish look, which pairs a calf-length white dress sock with The Row's ruched leather Soft Loafers. The supermodel's sister Kylie Jenner just so happens to own the same pair and recently wore them to power lunch with Kendall in Aspen. So the obsession with the Olsen twin-led luxury brand is a family affair.

A tiny pair of huggie hoop earrings completed the tequila mogul's outfit along with the brunette bob haircut she's had since November 2024. It's a much sportier vibe than we're accustomed to seeing from Jenner outside of an equestrian context, but it really works for her. Perhaps she'll trade her riding helmet for a lacrosse stick this summer.