Hilary Duff Returned To Late Night In A Wet-Inspired Runway Silhouette

Hilary Duff went on The Tonight Show With Jimmy Fallon on Mar. 10 after a 20-year hiatus (her first appearance with Jay Leno as the host), and let’s just say, the visit was long overdue. The singer-songwriter pulled double duty as both the guest and also the musical performer which called for two back-to-back dresses. Duff began filming in a black spaghetti strap square-neck and then slipped into an ivory thigh-high slit look once she took the stage to perform her single, “Roommates.” If you’ve seen The Lizzie McGuire Movie, the former teen idol, however, is no stranger to quickly transforming into a pop star.

Duff has been on, what feels like, a national press tour promoting her new album, Luck... or Something, which was released on Feb. 20. Since the last time the A Cinderella Story actor released new music was approximately ten years ago (and she didn’t tour then), there has been a lot of welcomed media attention surrounding her return. She’s giving millennial fans the perfect mix of what they want: a little Disney Channel nostalgia, details about being a mom to four kids, and some epic fashion moments.

Duff’s first look was a sleeveless faux pony hair midi dress by Helmut Lang. She wore the textured noir ensemble with a pair of matching patent leather pointed-toe pumps, her engagement ring, and a single dainty gold bracelet.

The next look was plucked from London-based Di Petsa’s Fall 2026 collection that just debuted last month (there were plenty of the thigh-high slits on the Paris and Milan runways this season). The brand derives much of its inspiration from Greek mythology and is known for its sheer wet-looking silhouettes. And since her music video for “Roommates” involved wet hair (and a potential nod to her 2003 hit, “Come Clean”), the seductive gown felt like the perfect outfit choice.

The singer wore the slitted number with a pair of PVC see through heels. Her hairstylist, Barb Thompson even greased up her hair to match the second look in between takes.

Let’s hope it doesn’t take a another 20 years to see Duff take the stage at 30 Rock.