Jimmy Kimmel Live! Weekly Highlights, 12-15 October 2026
This week, Jimmy Kimmel Live featured guests including Josh Brolin, William Shatner & Brad Paisley, Curtis "50 Cent" Jackson, Kate Berlant, Adam Brody, Tom Rhys Harries, Matchbox Twenty, Kim Kardashian, and Judd Apatow. Let's take a look at some of the outfits from this week's shows.
Josh Brolin
American actor Josh Brolin is best known for playing Thanos in the Marvel Cinematic Universe, Llewelyn Moss in No Country for Old Men, and Gurney Halleck in the Dune film series. For his appearance on the show, Josh opted for a smart-casual look. He paired slim-fitting, straight-cut trousers with a tucked-in white T-shirt and an indigo-wash denim jacket. He finished the look with shiny black leather ankle boots. Josh blended relaxed and polished elements for a put-together yet effortless look. The trousers and tucked-in T-shirt created a polished silhouette, while the denim jacket added a touch of ruggedness and texture to balance the outfit.
In his interview, Josh talked about the unsuitable movies he watched as a kid, the 74 films he thinks everyone needs to see, and his new film, Whalefall, coming out this weekend.
Curtis "50 Cent" Jackson
Curtis Jackson, better known as 50 Cent, is an American rapper and actor known for the songs "In da Club" and "Candy Shop" and the films Expend4bles and Boneyard. On the programme, he chose baggy white tailored trousers, a matching silk shirt, and a black and white checked jacket, finished with a white silk pocket square. The outfit reflects 50 Cent's signature flair, mixing street style with luxury. The shirt and trousers created an elegant monochromatic base, and the checked jacket added a striking pattern that provided visual contrast and a modern twist to the look of relaxed tailoring, sumptuous fabrics, and sharp details.
In this clip, 50 Cent chats about winning an Emmy for his documentary about Diddy, making a documentary series about himself, and his latest movie, Street Fighter, releasing on Friday.
Tom Rhys Harries
Welsh actor Tom Rhys Harries is famous for the series White Lines, Unforgotten, and Suspicion, and the film The Gentlemen. He wore mismatched, wide-legged greige tailored trousers; a single-breasted charcoal jacket with notch lapels; and a white, slightly sheer Henley top. He accessorised with a chunky silver watch and a modern thick silver ring. Tom's ensemble showcased a fashion-forward approach to tailoring. The deliberately mismatched trousers and jacket created an unconventional vibe, while the Henley top added a casual touch that softened the suit's formality. Modern accessories completed the outfit with a bold, personal feel.
During his conversation, Matthew discussed his Welsh origins, his upcoming film, Clayface, and whether Batman could beat his character.
Which celebrity outfit was your favourite?
Did Matthew's unconventional suit appeal to you, or did you prefer the looks worn by Josh Brolin, 50 Cent, or other guests this week?
If this week's celebrity styles inspired you, reach out to our talented tailoring team to create your own custom look.
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