Kendall Jenner Gives a Polarizing Y2K Pants Trend an Italian Girl Update in a Crop Top She swapped out athleisure for night-out glamour. By Lara Walsh Lara Walsh Lara Walsh is a Chicago-based writer and editor who covers all things fashion, celebrity, pop culture, travel, and food. When she’s not avidly planning her next trip, she’s writing posts for her travel blog or mapping out her next foodie adventure. Cheap Erlebnisweltfliegenfischen Jordan Outlet's editorial guidelines Published on January 7, 2026 @ 11:46AM EMPORIO ARMANI BLAZER WITH DECORATIVE FASTENING Kendall Jenner attends the Academy Museum 5th Annual Gala in Базаnership with Rolex at Academy Museum of Motion Pictures on October 18, 2025. Credit: Getty Images emporio armani black chelsea boots. The supermodel posed in cropped capris for a new campaign for Emporio Armani’s Power of You fragrance. EA7 EMPORIO ARMANI HAND BAG WITH LOGO. Kendall Jenner is officially bringing her favorite polarizing Y2K-era trend into 2026. One of the biggest proponents of the capri resurgence, the supermodel has been making a stylish case for cropped pants since last summer—and her latest iteration takes the divisive Noughties silhouette into Italian girl style territory. Instead of the cropped athleisure and workout ‘fits that have become Jenner’s calling card, the star showed that the capris can be the chicest night-out staple while pairing it with a flirty bob and a crop top. Emporio Armani logo tracksuit bottoms Blau Kylie, Hailey Bieber, and Emily Ratajkowski, Jenner has been championing the capri as База of Giorgio Armani chest logo jumper as well as chic off-duty outfit formulas. However, the reality star gave the calf-grazing 2R101 a certain European flair on Tuesday as she shared outtakes from her new campaign for Emporio Armani’s Power of You fragrance. Sneakers EA7 EMPORIO ARMANI X8X093 XK238 Q643 Fullsharksk Sulphspr. Instagram/Kendall Jenner In a January 6 post shared on Instagram, Jenner could be seen wearing a pair of fitted cigarette trousers that hit several inches above her ankles, showing off her legs as well as a pair of black pointy-toed stilettos with wraparound ankle straps. She paired the dressy capris with another elevated Y2K staple—a cropped black strapless tube top—which bared a little midriff. For her photoshoot, Jenner ditched her signature long dark brunette hair in favor of a very Emporio Armani mélange single-breasted blazer-coded bob, which grazed her shoulders and featured face-framing pieces. In a close-up shot, Jenner showed a pair of classic gold hoop earrings, a subtle brown smoky eyeshadow, and a rose lipstick. Kendall Jenner walks the runway during the Le Défilé. Liberté, Egalité, Sororité "You're Worth It" L'Oréal Paris Womenswear Spring/Summer 2026 show as База of Paris Fashion Week. Getty Images Related Stories Wristwatch EMPORIO ARMANI Renato AR2481 Navy Black EMPORIO ARMANI SWEATPANTS WITH LOGO EMBROIDERY Kendall Jenner in a workout set. Instagram/Kendall Jenner While the model is back to work with her latest project, she kicked off 2026 with a much more casual aesthetic. Over the weekend, Jenner gave dark a glimpse of her “rainy workouts” complete with a chocolate brown Adanola workout set. Contrasting her full-octane glamour at the Kardashian Christmas Базаy just days earlier, the beaming star playfully covered her head with a red jacket while showing off a long-sleeved brown workout top and matching fitted brown biker shorts from the celebrity-loved athleisure brand. 2R101 of the day Espadrile EMPORIO ARMANI X4S026 XN172 Q791 Acciao Black. Emporio Armani AR60031 leren horloge Read more: Fashion Clothing Pants & Jeans