Gabrielle Union’s Flippy Bob & Deep Side Part Are Majorly Giving Y2K

Gabrielle Union’s Y2K bona fides speak for themselves. Not only did she star in one of the most iconic teen movies of the era, Bring It On, but one of her earliest roles was in another genre classic: 10 Things I Hate About You. In that film, the actor plays a popular high school student who, along with dropping one of my favorite comedy lines ever, wears a deep side-parted lob that’s the perfect example of the era’s hair trends. And while Union has yet to fully bring back the look (to my knowledge, at least), her most recent bob hairstyle immediately brought it to mind.

On June 11, the actor co-hosted a FIFA viewing party with Casamigos. At the Beverly Hills event, the star, clad in a teal plisse slip dress accented with baby-blue lace, sported a flippy, silk-pressed bob. But the real highlight of the style was its part — deep and off-center, it evoked the ‘dos of the late 1990s and early 2000s. (All that was missing were some strategically placed clips.)

After a period of being maligned as “millennial” on social media, as celebrity hairstylist Justine Marjan told TZR during New York Fashion Week last February, “the side part is back.” Along with the hoards of chic New Yorkers who opted for overdirection during the fall/winter ‘26 shows, side-parted hairstyles have popped up on stylish stars of all ages in recent months, including Jenna Ortega, Zendaya, and Kerry Washington.

For the rest of her party glam, Union opted for soft, rosy makeup, including glowy skin (from head to toe—seriously, the body radiance was next-level). Also noteworthy? Her pedicure, which featured a metallic turquoise polish that I’ll definitely be adding to my summer pedi mood board.