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.
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.
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.
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.
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.
6. Offset & Quavo
NYC, September
How to be a good Migo: Wear Electric Kool-Aid Marc Jacobs fits to the Marc Jacobs fashion show.
7. Jake Gyllenhaal
L.A., June
When the gold chain is the new necktie.
8. Kristen Stewart
San Sebastián, Spain, September
Hollywood casting idea: K-Stew takes over for Depp in Pirates of the Caribbean.
9. Barack Obama
Durham, NC, February
Obama's Big Fit got huge when he had “44” embroidered on the sleeve.
10. Keanu Reeves
NYC, May
Keanu's fit is all black—except when it's brown. (And that's why we love him.)
11. Ralph Lauren
NYC, February
And then the Big Fit god looked over his Big Fit domain and saw that it was good.
12. Milo Ventimiglia
NYC, August
Why this outfit, Milo? “It was clean and comfortable.”
13. Justin Theroux
NYC, April
This fit would've made the top 15 even without the Supreme sticker.
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.
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."