The 58 Greatest Hawaiian Shirts of All Time
Fact: it takes quite the set of cojones to pull off wearing a Hawaiian shirt.
Also fact: most men don’t have ’em.
That being said, there are some real pros out there who do. And right now, we’d like to honor these brave souls who’ve unwaveringly taken up the charge. Through painstaking research—no scene left unexamined, no paparazzi shot ignored—we’ve uncovered the best and boldest examples of tropical-print artistry. A testament to confidence, these men are standards to aspire to. (At least when it comes to visually making a statement.)
So without further ado, and in no particular order, we present to you the 58 greatest Hawaiian shirts, ever.
1. Nick Nolte’s shirt, at his finest moment.
2. Mark Harmon’s in Summer School.
3. Bart Simpson’s in the episode entitled “Homer’s Phobia.”
4. Elvis’s apt attire in Blue Hawaii.
5. Tom Selleck’s wardrobe in Magnum, P.I.
6-7. Jason Segel and Jonah Hill’s resort-appropriate shirting in Forgetting Sarah Marshall.
8. George Clooney’s in The Descendants.
9. Any shirt Don Ho wore, since it becomes a Hawaiian shirt by proxy.
10. Morty Seinfeld’s shirt.
11. De Niro’s shirt in Cape Fear.
12. Nic Cage’s in Raising Arizona.
13. Johnny Depp’s rendition of Hunter S. Thompson.
14. Hunter S. Thompson’s rendition of… himself.
15-17. The Verona Beach wardrobe choices of Leonardo DiCaprio and company in Romeo + Juliet.
18. This shirt by Gitman Vintage that feels remarkably similar to theirs.
19-29. The ones adorning this lovely group of old Hawaiian men.
30. That of Ace Ventura, Pet Detective
31. Don Draper’s on his Hawaiian vacation
32. Roger Sterling’s shirt, when it was Pearl Harbor Day on Mad Men
33. Montgomery Clift’s shirt in From Here to Eternity.
34. … and Frank Sinatra’s in the same.
35. Steve Sanders’s tropical top in Beverly Hills, 90210’s opening credits.
36. Gérard Depardieu’s in My Father the Hero.
37. Val Kilmer’s brilliant shirting in Real Genius.
38. Al Pacino’s in Scarface.
39. Jeff “Chunk” Cohen’s shirt in The Goonies.
40. John Candy’s festive choices at all points of his career.
41. Wayne Knight’s shirt in the original Jurassic Park.
42. Andrew McCarthy’s lively print in Weekend at Bernie’s.
43. President Truman’s shirt that got him smiling.
44. Al’s always-eye-popping wardrobe on Quantum Leap.
45. Brad Pitt’s flamboyant shirts in Fight Club.
46. This gem on Jackie Chan.
47. Matt Damon’s shirt in The Informant.
48. Vince Vaughn’s holiday print in Four Christmases.
49. Dennis Quaid, morose at his participation in What to Expect When You’re Expecting.
50. Jon Lovitz’s second skin.
51-52. These two gentleman surfers.
53. Will Arnett’s shirt selections throughout Arrested Development.
54. This beauty by Battenwear, available for purchase now.
55. Chris Farley’s always-jubilant shirting.
56. Sir Jimmy Buffett.
57. Elliott Gould’s number in the film version of M*A*S*H.
58. The Brady Bunch, taking on Hawaii.
— Stephen Praetorius