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20 Best Hawaiian & Vacation Shirts For Men

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Is there anything more stylish and playful than a Hawaii shirt? Cosy and comfortable, it’s the perfect off-duty look all year round, but particularly in the warmer months. However, its origins weren’t so light and bubbly, as this piece of clothing became extremely popular during The Great Depression; but shortly after, the shirt developed a cult-like status and slowly started to sweep the mainstream. Even the King of rock n roll, Elvis Presley himself, began rocking vacation shirts in the 60s.

However, this staple piece of casual wear has endured for a long time, as after the 60s, Hawaiian shirts were then primarily affiliated with surf culture. Vintage lovers then embraced the trend, and now the shirt is at the forefront of the ‘Dad on Vacation’ aesthetic.

Hawaiian shirt FAQs

Are Hawaiian shirts actually Hawaiian?

Hawaiian shirts did actually originate in the 1920s in Hawaii when local Japanese women adapted kimono fabric to use in men’s tops. This piece of clothing became extremely popular in Hawaii; however, its initial name was the 'Aloha' shirt.

What is Hawaiian Shirt Friday?

Hawaiian Shirt Friday is where many corporate companies encouraged their staff to wear Hawaiian or Vacation clothing to work on Fridays to get them excited for the weekend. It's now a common workplace tradition by celebrating the end of the workweek by wearing casual attire (although not necessarily Hawaiian shirts) to the office on Fridays.

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If you’re looking to upgrade your vacation wardrobe (or just want to feel like you’re on vacay during your daily grind), we’ve rounded up which brands are creating the most stylish and fun Hawaiian shirts.

We’ve listed everything, from easy button-down collar shirts with minimalistic design to retro camp shirts with unique floral prints. You’re bound to find exactly what you need for when you’re sipping Pina Coladas by the poolside… or at home on your couch.

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