The 15 Biggest Fits of 2019

Each day on Instagram, we honor the best-dressed celebrity of the moment with the title #BigFitoftheDay. These are the 15 that loomed largest in 2019.
Andrew Lipovsky / Getty Images

1. Post Malone

NYC, August
Post Malone is partial to Bud Light and custom Crocs. So when he hit The Tonight Show in a perfectly appointed suit and spit-shined boots? There's your biggest fit of the year.


Raymond Hall / Getty Images

2. Marc Jacobs

NYC, September
No fashion designer has more fun wearing other designers' gear than legendary fashion fan Marc Jacobs—seen here in a Chanel jacket, Rick Owens boots, and a mean vape rig.


Jon Kopaloff

3. Pierce & Dylan Brosnan

L.A., July
How do you upstage the Once Upon a Time…in Hollywood premiere? Try hitting the red carpet with Thomas Crown—and dressing like you're the star of the film.

“Dylan showed up looking magnificent—very '70s. Right on the money.” —Pierce Brosnan
“It's all thrift-store stuff. I was wearing that two nights before. And my dad was like, ‘Well, just go in that!’ ” —Dylan Brosnan

Mike Smith / Getty Images

4. David Letterman

Cross River, NY, May
Real style translates across all activities—from a milk run to wetting a hook. Here, the head of Worldwide Pants brings the Big Fit franchise to the middle of a river in Pro Line waders and a Simms jacket.

“The only time I ever feel alive is when I'm wearing waders. I wear them to dinner, church, weddings, the theater, family gatherings, swimming, dancing, and around the house. The beard is fake. I only catch fish by accident.” —David Letterman

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5. Gwyneth Paltrow

NYC, May
Leave it to GP to wear a suit exactly the way we want to in 2019: slouchy, badass, and short enough to show off your shoes—on the day of the Met gala, no less.


Jamie McCarthy

6. Offset & Quavo

NYC, September
How to be a good Migo: Wear Electric Kool-Aid Marc Jacobs fits to the Marc Jacobs fashion show.

“I'm feeling the bell-bottoms, and the varsity jackets make me feel like I belong in the late '70s or early '80s. Ice Bells drip sells.” —Quavo

Albert L. Ortega

7. Jake Gyllenhaal

L.A., June
When the gold chain is the new necktie.


Carlos Alvarez

8. Kristen Stewart

San Sebastián, Spain, September
Hollywood casting idea: K-Stew takes over for Depp in Pirates of the Caribbean.


Gerry Broome

9. Barack Obama

Durham, NC, February
Obama's Big Fit got huge when he had “44” embroidered on the sleeve.


Angela Weiss

10. Keanu Reeves

NYC, May
Keanu's fit is all black—except when it's brown. (And that's why we love him.)


Carter Berg / Courtesy Ralph Lauren

11. Ralph Lauren

NYC, February
And then the Big Fit god looked over his Big Fit domain and saw that it was good.


James Devaney

12. Milo Ventimiglia

NYC, August
Why this outfit, Milo? “It was clean and comfortable.”


DIGGZY / SplashNews.com

13. Justin Theroux

NYC, April
This fit would've made the top 15 even without the Supreme sticker.


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14. Henry Winkler

NYC, April
Positivity is a Big Fit all its own. “I'm just so happy to be on this earth,” the Fonz tells GQ.


Chung Sung-Jun

15. Timothée Chalamet

South Korea, October
Timmy dons a full Sterling Ruby look and proves that in 2019 getting fitted is truly an art form.

A version of this story originally appeared in the December/January 2020 issue with the title "The Biggest Fits of the Year."