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Hawaiian Outfits for Men - 15 Hawaii Vacation Outfits for Men

Jenna Forti

Posted on July 04 2019


Aloha! We have compiled 15 Hawaii outfits for men and here is our detailed guide on what to wear in Hawaii in all four seasons.

If you have been to Hawaii before, you know what an amazing and diverse paradise it is. If you haven't, then it is surely a destination on your bucket list. Whether returning or a first timer, there is always something new to experience.

Hawaii is known for its laid back, easy going and playful lifestyle. Think fun aloha shirts and boardshorts everyday. When it comes to picking aloha shirts, there is a print for every occasion at Jams World. All of our prints are original hand-painted pieces of art selected from around the world that we screen print onto our exclusive spun-crushed rayon fabric. This natural fiber fabric is light, breathable and silky to keep you cool and comfortable in the Hawaiian heat.  Aloha shirts can easily be dressed up or dressed down for versatile looks, ideal for packing light.

When you get to Hawaii, you'll notice "support local" and "shop local" signs everywhere. Supporting local businesses is important to stimulate the economy and encourage sustainable business practices.

Jams World's commitment to community and quality has kept manufacturing in Honolulu since 1964. We encourage you to shop local while you're here and always look for that "Made in Hawaii" tag. 

What to Wear in Hawaii?

Mens Hawaiian Shirts - Flower Dream

1. Luau

Attending a "Luau" should be a priority on your Hawaii agenda. A luau is a Hawaiian party and feast, featuring traditional Hawaiian music, hula dancing, and "Ono" (delicious) food. A fun and colorful Mens Hawaiian shirt is a must, and our favorite is the Men's Retro Shirt in Luau Celadon art. 

Take a closer at a Jams World shirt, you'll notice there are custom hand-painted buttons coordinating with each print. An extra button accompanies each garment.

2. Sight Seeing - Traditional Hawaiian shirt

What makes a traditional Hawaiian shirt special is that the fabric is "engineered" so that the art work is continuous from the left side to the right side, including the carefully placed chest pocket. 

Our Men's Retro Shirt in No Ka Oi features famous landmarks and symbols representing Hawaii for the full effect.

Taking a closer look at the fabric, you'll see a map of the Island chain, the state fish, state flower, Hawaiian flag, Hawaiian coat of arms, the King Kamehameha statue, famous beaches and cultural scenes. "Hawaii No Ka Oi" translates to "Hawaii is the Best".

After your visit to the islands, we're sure you will agree. The No Ka Oi art comes in two color ways -- classic navy blue, and white. 

3. Dress it up - Black and White

For a fancier brunch or dinner reservation, a classic black and white shirt can make you feel modern and dressy. Jams World's black and white prints are far from boring, with the texture and depth of hand-painted art and quality that stands out from the rest. Our favorite is the Men's Rayon Shirt in Lily Moon art paired with white or black slacks and a subtle dress shoe.

4. Sunday Fun Day

You probably have something adventurous, or maybe a little crazy planned for your Hawaii trip. Whether it be a stand up paddle, jumping out of a helicopter, or a Booze Cruise, we've picked out the perfect "fun day" shirt for you. Santa Monica art is vibrant, eye catching, and can be worn from the Islands to the California Coast.

5. Vibrant and Floral

Stand out of the crowd with something vibrant and floral. Tropical Love Art offers impactful texture and depth replicating the original hand-painted art. This print pairs easily with black or denim to match whatever else you threw in your luggage.

6. Island Hopping

The state of Hawaii is an archipelago comprised of eight main Islands, each with different experiences awaiting. Oahu is home of the famous Waikiki and the state capital of Honolulu, not to mention home to the Jams World Factory. The state is named after the largest of the chain, nicknamed "Big Island". Maui, Kauai, Molokai, Lanai, Niihau und Kahoolawe complete the archipelago. We suggest starting your vacation on Oahu and "Island Hopping" to experience all that you can.

Anahola Bay art is inspired by the famous white sand beach on the island of Kauai. This print draws from Kapa or traditional Hawaiian cloth design motifs. We picked this shirt as a tribute to Hawaiian culture found across the archipelago. Anahola Bay comes in two colors, offering cool blue ocean tones or a neutral earthy color palette for an understated island look. 

7. Mai Tais in Waikiki

A fun and colorful Jams World shirt will easily bring a conversation your way when you go to Waikiki Beach for a Mai Tai. Duke's Waikiki is known for the best Mai Tai with the perfect view of Diamond Head. This is a must for your bucket list if it isn't on it already. We suggest the Men's Retro Shirt in Parrot Cove, a worldly art piece hand-painted by an Italian artist.

@Oscarnn (via Instagram) wears it here at a pool party at The Surf Jack Hotel & Swimclub, a colorful boutique hotel just off the Waikiki strip, known for Instagram-worthy coffees and pool parties that makes you "wish you were here".

8. A Night Out

Honolulu is a one-of-a-kind city. You can get the buzz of city life, while still feeling the laid-back, island lifestyle. We suggest pairing an aloha shirt with a blazer for a sleek island look on an evening out for drinks. (Photo courtesy of @mb1ack via Instagram).

Wondering where to go for a night out in Honolulu? Sky Waikiki offers the best rooftop view of Waikiki with a cantilevered deck over Kalakaua strip, perfect for Sunset drinks and you can dance the night away on the weekends, too. RumFire at The Sheraton Hotel, Addiction Nightclub at The Modern Hotel, and "First Fridays" on the first Friday of each month in Downtown Honolulu are some popular go-to's for locals. 

9. Date Night

If you didn't hear yet - twinning is in. Wearing a matching Hawaiian dresses makes date night so fun. Don't forget to take pictures and tag us @jams_world #jamsworld when you do. Our favorite twinning print is Blue Jay, with the perfect balance of masculine and feminine in the cool color palette and tropical design.

10. Aloha Friday

This limited edition Aloha Art is perfect for your Aloha Friday experience. "Aloha" is a greeting word that can literally be defined as "hello", "goodbye", and "I love you", but aloha is more than just a greeting. The "aloha spirit" is a way to live, with friendly, generous, and loving energy. The aloha spirit is what makes Hawaii different from any other place in the world.

On Fridays, locals put on their aloha shirts and celebrate the end of the work week with "Pau Hana" (done with work) drinks.  If you are looking for something special to do after sunset drinks, the Hilton Hawaiian Village puts on a fireworks show at 7:45pm every Friday.

11. Museums and Cafes - Viola Twist

For coffee shops - Ars Cafe (doubles as an art gallery), Kona Coffee Purveyors, Morning Glass, and Arvo Cafe are some local favorites. The Honolulu Museum of Art, Shangri La (Doris Duke), and the seasonal Honolulu Biennial are great if you're looking for unique art experiences.

A contemporary, abstract geometric piece of art like Viola Twist is perfect when visiting cafes and museums around Honolulu. You will fit right in with the artsy, hipster aesthetic while wearing #WearableArt yourself. Viola Twist pairs nicely with denim and white. Complete the look with white sneakers for a steezy look. 

12. Kakaako Street Art

Honolulu has an amazing street art presence including Pow Wow Worldwide artwork along the streets of Kakaako. Checkout the neighborhood and look the part wearing a piece of #WearableArt like this Tweet print Jams World shirt. This particular art piece is an original hand-painted piece by a contemporary artist from Europe. DJ and photographer, Mason Rose (@masonrosephoto on IG) from The Lucky Kids band (@theluckykidz on IG) featured here.

13. Effortlessly Cool - Original Jams 80s Boardshorts

Jams World is deeply rooted in 1960s surf culture. Founder, Dave Rochlen, started off with a surf board shop called Surf Line Hawaii. In the first decade of boardshort invention, he had the idea to cut a pair of colorful pajama pants at the knee and surf in them. "Jams" short for pajamas, were born. Beaches would never be the same. Original Jams became iconic, with the trend peaking in the 80s as "crash colors" caught on with the college kids. Surf Line Hawaii has reimagined the Original Jams concept for the next generation, in a technical board short form. These shorts are perfect for lounging at the beach, then throwing on a plain white tee for an effortlessly fashionable look. The full hawaiian outfits is available on the Surf Line Hawaii website.

14. Beach Party - Party Wave Boardshorts

An original print from the Surf Line Hawaii 60s archive, Party Wave is as authentic as it gets. When the surf is fun and a group of surfers share a wave, locals call it a  "Party Wave". Make sure to share waves and have fun when wearing these shorts.

Micah Liana (@ulumicahs on Instagram) shows us how fashion meets function with the Party Wave boardshorts. 

15. North Shore - Alii Boardshorts

Take a trip from Honolulu to the country side to see the famous beaches along the North Shore of Oahu. Tip - Drive along the East Side for a scenic route. Stop at Waiahole Poi Factory along the way for the best authentic Hawaiian food on the island. Make sure to drive through Old Haleiwa Town for an açaí bowl from Haleiwa Bowls or shave ice from Matsumoto Shave Ice for the full experience.

A pair of Surf Line Hawaii Classic Mens Boardshorts and some "slippers" (flip flops) will have you fitting right in with the locals. Our favorite of the Hawaiian inspired color ways is "Ali'i", with red and yellow tones resembling the intricate feather capes worn by Native Hawaiian Chiefs, known as Ali'i. 


You have read our detailed guide on what to wear in Hawaii

Now I’d like to hear from you:

What dresses you would bring on your Hawaiian trip?

Let me know by leaving a comment below right now.

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