Estimated read time2 min read

For anyone obsessed with Old Hollywood gowns, dramatic fur and feather details, and shimmering sparkles, Olivia Dean’s The Art of Loving Tour has been a sartorial dream. The artist has spent her summer on the move, gracing stage after stage in all the Self Portrait rhinestones and Etro fringe one could ever wish for. And for her latest stop, at New York City’s Madison Square Garden, she turned to Gucci.

Olivia Dean in Gucci

Lola Mansell

Styled by Simone Beyene, the glistening evening gown was pulled from Demna’s Pre-Fall 2026 Generation Gucci collection, a line of vintage-inspired pieces that borrowed style codes from the house’s rich history. For this particular dress, the creative director flipped back through Gucci’s 1990s archives, bringing the sleek silhouettes and body-hugging shapes of the decade into present day. The result was a shiny silk-chiffon piece with a high halter neckline, deep low back, and all-over embroidery.

The cross-generational feel was only enhanced by Dean’s bouncy blowout, which added an extra retro-glam touch.

The artist wore the striking gown on August 17, during the penultimate night of her four-night MSG run. During the show, she treated fans to all the hits from her second studio album, The Art of Loving, including “Nice to Each Other,” “Lady Lady,” and “Man I Need.” She also sprinkled in some fan-favorites from her earlier projects, including 2019’s “OK Love You Bye” and 2023’s “Dive.”

Last fall, Dean joined the growing list of artists fighting for fair ticket pricing, calling out Ticketmaster and declaring that “live music should be affordable and accessible.” She kicked off the tour the following April, and has since taken it from the United Kingdom to mainland Europe and now overseas. Next up: Australia and New Zealand!