Traditional glamour always rules on the red carpet—but the best dressed stars are always the ones who push the envelope a little bit further. This week, the A-listers who stood out on the fashion scene were those who mixed classic silhouettes with contemporary finishes—making for interesting end result that were more avant-garde, and way more fun.

Take Chappell Roan, who attended the Daily Front Row Fashion Awards in Beverly Hills wearing a floral McQueen frock with sculptural sleeves and a pleated high-neck collar. It was not at all your typical red carpet dress—is anything, by way of her stylist Genesis Webb?—and was totally worth the risk. The same goes for actor Jodie Turner-Smith in London: The star hit the Thunderbolts* premiere in a Burberry silky blouse and sporty pleated skirt, a stealthy-chic look that stood out among a sea of glitzy gowns.

Even the more Old Hollywood-worthy dresses this week gave us unexpected twists. At a Tiffany & Co event in New York City this weekend, Taylor Russell chose a powder-blue chiffon Connor Ives gown that featured a sweeping train and wide-open sides—showing a dash of skin. At the Planned Parenthood New York Gala in New York City, Olivia Rodrigo slipped into a white halter-style Gucci design with a dramatic leg slit and bejeweled Horsebit clasp. The week was all about timeless silhouettes, just with more updated and modern finishes.

Which were your favorite celebrity looks this week? Vote below, and check back on Friday to see who Vogue readers crowned best dressed.