Never one to shy from a playful fashion moment, Jennifer Love Hewitt brought a vibrant, Y2K-era energy to the premiere of “Road Trip” in Los Angeles on May 11, 2000.
The beloved actress, a quintessential face of late ’90s and early 2000s cinema, arrived in an ensemble that perfectly encapsulated the fun-loving spirit of the era. Hewitt’s striking orange top, heavily adorned with intricate beading, was the undeniable centerpiece of her look. Its relaxed, sleeveless silhouette offered a playful contrast to the dazzling embellishment, catching the light with every move. The vibrant hue spoke to a burgeoning optimism in fashion, a departure from the grunge-infused minimalism of the decade prior.
Never one to shy from the spotlight, tennis phenom Anna Kournikova brought her signature blend of athletic charm and casual allure to a signing event for For Him Magazine (FHM) at the Virgin Megastore in New York City on September 6, 2001.
The global sports icon, whose striking looks frequently graced magazine covers, celebrated her FHM feature in an ensemble that felt both approachable and undeniably chic. Kournikova opted for a vibrant red satin-blend shirt, its lustrous fabric and tie-front detail adding a touch of playful sophistication. The color popped, perfectly complementing her long, golden blonde hair, which cascaded around her shoulders.
Never one to shy from a sartorial power play, Miley Cyrus brought a sleek, almost enigmatic allure to the “Something Beautiful” party at Rough Trade East in London on June 21, 2025.
The multi-hyphenate star stepped out in a look straight from the Tom Ford Fall 2025 collection, cementing her status as a muse for contemporary luxury with a rebellious streak. Cyrus chose a subtly cropped pullover sweatshirt in black, its relaxed silhouette playing off the unexpected reveal of her midriff, a quintessential Miley touch that always keeps you on your toes.
