Best Hawaiian Shirts 2021: Classic Hawaiian Shirts to Wear on Vacation - Rolling Stone
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These Are the Hawaiian Shirts We’re Packing Right Now

The best Hawaiian shirts to wear this summer, with picks from Tommy Bahama to Saint Laurent

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A couple years ago, some clever trend-setters pulled their dads’ Hawaiian shirts out of the closet. The results were even better than anticipated, and the trend breathed new life into the mid-century summer staple. Today, you’ll find fashion-savvy dudes rocking Hawaiian shirts everywhere from Los Angeles to Paris – not to mention beaches and pools everywhere. And brands have taken notice, producing some of the best Hawaiian shirts ever.

What Are the Best Hawaiian Shirts?

If you’re looking to update your summer wardrobe, a good Hawaiian shirt (a.k.a. vacation shirts) are now essential. Thanks to the piece’s revitalization, you can find vacation shirts in just about every color and pattern. The best Hawaiian shirts are also much easier to wear now than they were back in the fifties and sixties: Guys are now rocking vacation shirts with jeans and boots, sneakers and chinos, casual suits and, of course, swim trunks and sandals.

Below are some of our favorite Hawaiian shirts to buy this summer.

1. SSS World Corp Hawaiian floral print shirt

Thanks to the eye of SSS World Corp’s founder and head designer, Justin O’Shea, the brand has become a low-key hit with a cult following. They’re known for bold, rock n’ roll inspired looks, and this Hawaiian shirt is no exception. It’s a throwback summer staple with some edge and looks just as good at the beach as it does at trendy urban bars.

hawaiian shirt mens sss world corp

Courtesy Farfetch

Buy: SSS World Corp Hawaiian Shirt at $218.00

2. Paul Smith Floral Vacation Shirt

This vacation shirt from Paul Smith does an impressive balancing act between pulled-together and playful. It features a lyocell-cotton blend that’s breathable enough for hot weather and relaxed enough for hardcore vacationing. The print is eye-catching without being too bold, making it easy to wear with most pieces in your current spring/summer wardrobe.

white hawaiian shirt paul smith

Courtesy END.

Buy: Paul Smith Floral Vacation Shirt at $195.00

3. Drôle de Monsieur Floral Vacation Shirt

Drôle de Monsieur is a french brand with clothing built for the Riviera. Case in point is this floral vacation shirt. It’s got all the fixings of a classic Hawaiian shirt (camp collar and slouchy rayon-cotton material) plus a bold print that’s old-school yet subtly unique. The shirt is obviously at home with shorts and flip-flops, but we also like it with pants and loafers for a summer night out.

hawaiian shirt mens floral

Courtesy END.

Buy: Drôle de Monsieur Floral Vacation… at $259.00

4. Shinesty The Palm Desert Hawaiian Shirt

If you want full-on pool party vibes, check out this Hawaiian shirt from Shinesty. The shirt is a great example of the brand’s playful spirit with neon palm trees and leopards over a striped background. The material is 100% rayon for an extra-slouchy fit, and the shirt goes best with, well, anything summery (and a piña colada).

crazy hawaiian shirt shinesty

Courtesy Shinesty

Buy: Shinesty The Palm Desert Hawaiian Shirt at $59.99

5. Polo Ralph Lauren Reef Vacation Shirt

Ralph Lauren might be famous for their preppy aesthetic, but the brand has always been a great source for Hawaiian shirts as well. We like this one because it’s subdued yet whimsical with a white and navy reef scene print. The shirt is 100% cotton, providing a bit more structure than some vacation shirts, but it certainly knows how to relax nevertheless.

blue vacation shirt mens ralph lauren

Courtesy END.

Buy: Polo Ralph Lauren Reef Vacation Shirt at $79.00

6. Allsaints Hana Floral Camp Shirt

We like when brands try something different with the floral print of Hawaiian shirts. Allsaints does this – and does it well – with this vacation shirt. It features several clusters of tropical flowers with spacing to show off a unique brown background. The shirt is also 100% viscose, lending a droopy, flowy fit.

hawaiian shirt mens designer

Courtesy Nordstrom

Buy: AllSaints Hana Floral Camp Shirt at $139.00

7. Tommy Bahama Piña Paradise Silk Button-Up Shirt

The undisputed king of Hawaiian shirts is and always has been Tommy Bahama. They’re still making some of the best vacation pieces around, such as this Piña Paradise shirt. It’s 100% silk to match any five-star resort in laid-back luxury, and the tropical foliage print is classic through and through. You can totally wear it in the city, but be warned: you might end up booking a vacation.

hawaiian shirt tommy bahama

Courtesy Nordstrom

Buy: Tommy Bahama Piña Paradise Button-Up… at $140.00

8. Benson Tropical Floral Print Camp Shirt

Benson proves that although bold and colorful is great, it’s not the only way to approach Hawaiian shirts. This piece features a white background with an outlined floral print all over. It’s reserved and minimal, making it great for wearing to dinner or drinks anywhere, but still at home on vacation.

white vacation shirt mens

Courtesy Nordstrom

Buy: Benson Tropical Floral Print Button-Up… at $145.00

9. Versace Sea Scene Vacation Shirt

On the bold side of Hawaiian shirts are pieces like this Versace Sea Scene shirt, covered with the brand’s famous Trésor de la Mer print. It’s unmistakably a special piece with a wide, boxy fit and three front pockets, in addition to the eye-catching print. We think it looks best when contrasted with subdued pieces (think, monochrome swim trunks and white sneakers) but it can certainly work with maximalist outfits too.

designer vacaiton shirt versace

Courtesy END.

Buy: Versace Sea Scene Vacation Shirt at $739.00

10. Ralph Lauren RRL Postcard Shirt

Every once in a while, RRL drops a different version of this postcard/scrapbook shirt. They sell out fast because people like us can’t get enough of the shirts’ vintage aesthetic and unique photo prints. This one features photos of sailors on leave during the forties – or, in other words, photos of everyone’s dream tropical vacation.

vacation shirt mens ralph lauren

Courtesy END.

Buy: Ralph Lauren RRL Postcard Shirt at $149.00

11. Saint Laurent Hawaiian Print Shirt

Like many throwback staples, high-end designers have a way of making Hawaiian shirts special. This Saint Laurent vacation shirt, for example, has a classic floral print that’s just somehow more considered and distinct than others. This one also has a straight-point collar (slightly more structured than the normal camp-collar) that lends some seventies vibes.

saint laurent floral shirt mens

Courtesy Farfetch

Buy: Saint Laurent Hawaiian Print Shirt at $790.00

12. Amiri Relaxed Fit Faded Aloha Shirt

Amiri took a more trans-continental approach to this fast-selling Hawaiian shirt, bringing some Japanese aesthetics into the print. We think it worked very well. The print and fading at the bottom make the piece special in a sea of florals, and the red background sets it apart even more. Plus, with a 100% silk construction, it’s about as luxurious as Hawaiian shirts come.

hawaiian shirt designer amiri

Courtesy Nordstrom

Buy: Amiri Relaxed Fit Faded Aloha Shirt at $890.00

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