How to Wear a Hawaiian Shirt in 24 Different Ways

17th Sep 2019

• Part of our How to Wear It series •

How to Wear a Hawaiian Shirt in 24 Different Ways

by Madeline Berger
September 17, 2019 | Last Updated: January 7, 2021

With major trends of the ’80s here to stay this season, we’ve been seeing Hawaiian shirts everywhere this past year and expect them to stick around well into 2021. If you’re one of the silly few who believe Hawaiian shirts exist solely as vacation-wear, think again: we’ve gathered up twenty-two different ways to style the classic shirt below. Check out looks from style savants at and Instagram and shop our vintage Hawaiian shirts and new Hawaiian shirts while you’re at it.

Credit: Caleb Paulson

1. Work your Hawaiian shirt as a mid layer over a plain white tank and shiny black bomber.

Credit: @barbieferreira

2. Take it on the road and tuck your Hawaiian shirt into jeans with a suede overshirt for a subtle Western nod!

Credit: Enea Nastri

3. Loosely tuck your Hawaiian shirt into a pair of trousers to put a business spin on your outfit.

Credit: Lua P

4. Layer up: start with your favorite graphic tee, add a Hawaiian shirt, and finish with a fuzzy sweater.

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Credit: @pamelatick

5. Enjoy that summer rooftop cocktail with a loose Hawaiian tossed on with denim shorts and a woven belt.

Credit: Franklin Benitez Upegui

6. Franklin serves a slick look by pairing an oversized Hawaiina shirt with a body-skimming black tee and belted black jeans. Slick as heck!

Credit: K Chola

7. Tuck a buttoned-up oversized Hawaiian shirt into a denim skirt of any length. Don’t forget your favorite accessories!

Credit: Sabina T

8. Take a super oversized Hawaiian and belt it, creating a faux dress. Add shorts if necessary!

Credit: Paul Jatayna

9. Pattern-clash: we love how Paul layered a pair of Hawaiian print shorts over leggings to go with his top.

Credit: Juliea Kehoe

10. An open Hawaiian shirt with a crop top and sunglasses is the perfect answer to summer sun (or a night out).

Credit: Ragstock

11. Play with pattern by mixing a Hawaiian shirt with camo pants. Keep proportions in play by matching with a coordinating tube top.

Credit: Polyhrones Tatsis

12. Break up that Canadian tuxedo with an unexpected twist—a Hawaiian shirt! Add statement shades to make it next level.

Credit: Charlie Cole

13. Give your Hawaiian shirt an edge by throwing on a leather biker jacket, adding bottoms in a complementary hue.

Credit: Ragstock

14. We loved styling this vintage Hawaiian shirt with a pair of white shortalls for an unexpected summer outfit.

Credit: Ellie Nik

15. Get a little punk with an oversized Hawaiian, classic jeans, a necklace or two, and large white socks. 

Credit: Mwandu S

16. We love the unexpected pairing of a vintage Hawaiian shirt under overalls (or shortalls and tights!).

Credit: Christian Meltzer

17. With biker shorts all the rage, add a large Hawaiian shirt on top to play with dimension and volume.

Credit: Megan Marshall

18. Layer a Hawaiian shirt over a mock-neck sweater for a solid transitional fall outfit.


19. Have a pair of Hawaiian-print shorts on hand? Pack a real punch and wear ’em together.

Credit: Annie B

20. Tie a knot at the front of your Hawaiian shirt to create a crop top, and pair with your favorite mini.

Credit: Robbie Cook

21. Roll up the sleeves and pair with some trainers and your favorite pair of vintage denim jeans.

Credit: Ruth Noemi Bendel

22. Show a little skin: keep most of your Hawaiian shirt unbuttoned to add an unexpected element to your ‘fit.

Credit: Andre Judd

23. Layer a printed blazer over your Hawaiian shirt and add a heap of accessories. More is more, people. 

Credit: Sophie BT

24. Tuck a buttoned Hawaiian shirt into a denim or leather mini skirt, accessorizing with a hair bow and sunglasses for a true vacation vibe. Just add the ocean!

Feeling inspired? Get shoppin'! We stock a wide variety of both new and one-of-a-kind vintage Hawaiian shirts so you can find exactly what you're looking for.