Chris Pine Wore Pajamas To The Set Of Jimmy Kimmel Live!, Then Revealed Why He Chooses Such Wild Outfits

Darren Barrenman (Chris Pine) speaks into a microphone during a scene from Poolman.
(Image credit: Vertical Entertainment)

People have debated for years which Hollywood A-lister is most deserving of the “best Chris” title, but regardless of what Hemsworth, Evans or Pratt may be doing on the big screen, it’s Chris Pine who’s been showing the most bizarrely spectacular looks when it comes to fashion. After showing up to the set of Jimmy Kimmel Live! in pajamas and an overcoat, the Poolman star revealed that he’s got a reason for dressing the way he does.

Chris Pine’s latest movie Poolman hit theaters this weekend, and anybody who’s paid any attention to the promotion of the film likely saw the actor channeling his character in shorts, a blazer and hiking boots at the premiere in April. Things got a little more casual for his trip to Jimmy Kimmel Live!, as he arrived wearing a matching green-and-white pajama top and bottom set, along with a navy overcoat. Check out the bold look below: 

Chris Pine arrives to the set of Jimmy Kimmel Live! wearing green and white pajamas and a long navy blue overcoat in May 2024.

(Image credit: Photo by JOCE/Bauer-Griffin/GC Images)

I have to admit, my favorite part of this look — which he paired with brown huaraches — is the pocket square he added to his long blue blazer. It gives a classy kick to the robe vibes.

Chris Pine did change out of his PJs before taking the stage with Jimmy Kimmel, adorning a matching white linen set with a few sporadic vertical stripes, but the late-night host seemed eager to address how the Don’t Worry Darling’s fashion choices have become “more outlandish” in recent years. While first attributing his new look to “too many mushrooms,” Pine then explained: 

It’s a comfort thing, you know? It’s LA, we have a different kind of mode for dressing. I like to have a good time. Life is too hard, it’s gonna make you giggle if you put on some funky linen pants. Life’s pretty simple.

I actually love that explanation. We deal with enough in life, so when it comes to what we wear, why shouldn’t we be having some fun and staying comfortable with it? 

Jimmy Kimmel recalled a few of his past looks as well, including Chris Pine’s viral short shorts, and the actor again namedropped Magnum, P.I. himself, Tom Selleck as his inspiration. Pine said: 

I’m a big fan of Tom Selleck and as we know, Tom Selleck liked a short short.

In addition to his outfits, Chris Pine has turned heads with other elements of his look, growing out a shaggy beard and styling his long hair in a way that got him roasted for looking like Rachel from Friends. He also apparently purchased a fanny pack to help him stay in character while filming Wonder Woman 1984

Hopefully the release of Poolman to theaters won’t mean the end of these eccentric fashion choices, because I am 100% here for the short shorts and pajama looks. Head to the theater to see the wild wardrobes he sports in the movie, too, and be sure to check out our 2024 movie release calendar to see what else is headed our way soon. 

Heidi Venable
Content Producer

Heidi Venable is a Content Producer for CinemaBlend, a mom of two and a hard-core '90s kid. She started freelancing for CinemaBlend in 2020 and officially came on board in 2021. Her job entails writing news stories and TV reactions from some of her favorite prime-time shows like Grey's Anatomy and The Bachelor. She graduated from Louisiana Tech University with a degree in Journalism and worked in the newspaper industry for almost two decades in multiple roles including Sports Editor, Page Designer and Online Editor. Unprovoked, will quote Friends in any situation. Thrives on New Orleans Saints football, The West Wing and taco trucks.