Jimmy Kimmel Live! Weekly Highlights, 28 September-1 October 2026

This week, Jimmy Kimmel Live featured guests including Pete Davidson, New York City Mayor Zohran Mamdani, TV On The Radio, Howard Stern, Amy Schumer, Tom Morello, Billy Crystal, Mahershala Ali, Audrey Hobert, John Oliver & Seth Meyers, Robby Hoffman, Paul McCartney, Sen. Bernie Sanders, and Goose. Let's take a look at some of the outfits from this week's shows.

Pete Davidson

American comedian and actor Pete Davidson, known for Saturday Night Live, The King of Staten Island, and Bupkis, appeared on the show in black trousers, a white T-shirt with a black collar, and a leather bomber-style jacket. The bomber jacket paired with crisp white trainers gave his outfit a fresh, fashion-forward edge, and the unusual contrast between the sporty footwear and the tailored trousers added a playful, unexpected vibe.

During his interview, Pete talked about getting two concussions while filming his new movie, How to Rob a Bank, getting buff for it, buying the Staten Island Ferry with Colin Jost, and filming his podcast in his garage.

Billy Crystal

Billy Crystal, an American actor recognised for films such as When Harry Met Sally, City Slickers, and The Monsters, Inc. franchise, also opted for a smart-casual look. He paired skinny black jeans with a graphic tee under a black tailored jacket. The jacket featured slim lapels and a structured silhouette, contrasting with the unfitted T-shirt. The casual jeans and T-shirt created a relaxed, comfortable look, which was elevated and modernised by the addition of the tailored jacket. He finished the outfit with black leather trainers with white soles.

In this clip, Billy chats about working with Robert De Niro on Analyse This, losing his home in the Palisades Fire, and his new Broadway show, 860.

Mahershala Ali

Academy Award-winning American actor Mahershala Ali is famous for his roles in Moonlight and Green Book. For his appearance, he chose a monochromatic ensemble featuring a dove-grey, subtly striped shirt and matching, slightly flared tailored trousers. His accessories included a black knitted cap, tinted glasses, and silver-toned diamond jewellery. The tonal colours created a cohesive, eye-catching effect, while the stripes and gentle flare of the trousers added a fresh, clean silhouette. The accessories broke up the monochrome and added personality and a touch of glamour to the ensemble.

During his conversation, Mahershala discussed many topics, including playing a hitman in his latest film, Your Mother Your Mother Your Mother.

Which celebrity outfit was your favourite?

Did Billy Crystal's elevated casual look appeal to you, or did you prefer the outfits worn by Pete Davidson, Mahershala Ali, or other guests this week?

If you're inspired by this week's celebrity styles, reach out to our talented tailoring team to create your own custom look.

 

 

 

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