Hawaiian shirts might be the toughest buy in menswear. The traditional ones—the ones you immediately think of—are reserved for the backs of cruise-booking fathers and retired islanders. If you walk into a bar wearing one of these, everyone will know. When you’ve got on the “island gift shop” Hawaiian shirt, you’re going to get clowned. The colors are tacky, the fit is boxy and unflattering, and the collar will never keep its shape.
So, when you’re buying a Hawaiian shirt this year, look for quality. The best way to look good in yours is to shell out that extra $50, $100 to look good and not gimmicky. There’s a fine line here between total flop and perfect choice. Here are eight Hawaiian shirts that every guy can pull off.
J.Crew Island Print
This “Island Print” shirt by J.Crew is a great buy both because of its print—a painted, vintage-y island scene—and its fit. The fit is slim, with rolled sleeves and a spread collar. It’s the perfect shirt to pair with a lighter wash pair of jeans or a deep navy suit. $60
Brooks Brothers Tropical-Print
Yes, Brooks Brothers tried their hand at a Hawaiian shirt. And, as expected, it’s of the utmost quality. The print is tropical and bold and the shirt is structured and meant to last. If you happen to have an off-white linen or silk suit, this would go perfectly with it—just saying. $60
Polo Ralph Lauren
Again: here’s an American classic in menswear doing their best rendition of the Hawaiian shirt. This time it’s Polo Ralph Lauren, but the same goes. It’s a bold pattern with great structure. The collar is buttoned-down and the sleeves aren’t rolled, which makes this shirt perfect for casual Friday at the office. $100
Proper Cloth Japanese Black and White Aloha Floral
Here’s the perfect Hawaiian shirt for the monochrome man. If you’re into—even when it’s hot out—wearing all black, this shirt from Proper Cloth is meant for you. It’s a classic and elegant pattern printed on the finest fabric; and, for a few extra dollars—literally, for most additions it only costs $10 or $15—you can customize every detail of the shirt from the collar to the buttons. $125
ALLSAINTS Offshore
ALLSAINTS is the best mid-level luxury brand to invest in. You’re going to get the same quality you’d get from Yves Saint Laurent or Prada, at a fraction of the price. It still isn’t your cheapest option, but if you want to look good in your Hawaiian shirt, quality over quantity—always. And, this is by far the most toned down shirt on the list. $130
River Island Black Foil Leaf
Did you get invited to a black tie event in the dead of summer? Torn between looking great and surviving? Yes, it’ll be hot, and you’ll probably see at least a couple of brave souls decked out in tuxedos, but, you can look just as good—probably better—in this shirt and a breathable black suit. You’ll feel aerated, and you’ll look like a million bucks. $56
SSS World Corp Vice
This is the “Aloha from Hell” shirt. From a distance, it looks like your standard vintage hula-girl print. But up close, it’s skull-faced girls dancing to a ghoulish beat. It’s the perfect edge for the classic shirt, and it’ll get you compliments from dads and rockers alike. $146
Tommy Bahama Coco Colada Camp
The intro to this piece would lead you to believe that you should steer clear of the dad-shaped Tommy Bahama shirt. But, this one is uniquely self aware. Donned the “Coco Colada Camp Original Fit” shirt, this one will fit looser on purpose—not because they don’t know any better. It’s 100% silk, and blessed with the original embroidered Tommy Bahama “Pineapple and Hula Girl” logo. It’s worth the $155 for the high-quality vintage look. $155
