There’s just something about wearing a pineapple Hawaiian shirt that makes you feel like you deserve to kick your feet up on a beach chair with a fruity drink in hand. And in my family, it involves a lot of bad dad jokes.

So, we could not help but round up some of our favorites to help you all kick off summer the right way. Whether you are planning to vacation to Hawaii soon or just laying out by your backyard pool daydreaming of Hawaii these are the shirts for you! Check out our 15 favorite Pineapple Hawaiian Shirts below. 

---

The Best Pineapple Hawaiian Shirts

Aside from helping you out in the fashion department, we have tons of tips & tricks to help you have the Hawaiian vacation of your dreams. We’ve got everything you need to know about budgeting for a trip to Hawaii here. You can find Hawaii packing tips here, and tips for choosing the best island for your family here!

---

Dad’s Style Pineapple Shirts

When you think pineapple Hawaiian shirts, I know the first thing that comes to your mind is Dads. That said, our first selections are the perfect Hawaiian shirts for Dads!

---

The Resort Shirt

This resort shirt has a dark navy blue base and small pineapple print throughout it. We loved that it has an option to match with another family member if you want.

The shirt is made with a soft, relaxed fabric so you can chill on your vacay. Be sure to check the size chart to get the perfect fit! Check it out here.

---

The Pineapple Graphic T-Shirt

This pineapple graphic tee is a fun yellow color! The design is simple, bright and fun! How cool is that? I think this graphic tee is perfect for chilling at the beach. Check it out here.

---

The Hawaiian Button-Down Shirt

You can’t go wrong with a classic men’s Hawaiian shirt, especially if it has pineapples on it! This button-down shirt has a poplin fabric, making it comfortable to relax on the beach. Check it out here.

---

The Pineapple Print Button Down

This Pineapple print Hawaiian button down is so chic and great for those warm nights in Hawaii! Check it out here.

---

The Pineapple Print Tee

This pineapple print tee has a design with a black and white pineapple, and gray background. This shirt is super cool for your Hawaii vacay. Check it out here.

---

Shop Our Picks for Dads

---

Pineapple Hawaiian Shirts for the Ladies

We cannot leave out the ladies who want to rock a pineapple Hawaiian shirt on vacation!

---

The Chic Hawaiian Top

I love the flutter sleeves on this shirt paired with the classic button-up look. This shirt can be paired with jean shorts for a casual look, but you could also dress it up! Check it out here.

---

Pineapple Print Blouse

This pineapple blouse has a fun summery vibe. It has a cute yellow and pink pineapple print. Check it out here.

---

Pineapple Print Tee

This pineapple print tee is perfect for vacationing in Hawaii. It has a pineapple print with the words pineapple on the tee. Check it out here.

---

Pineapple Print Romper

This flowy pineapple romper can rival any Hawaiian dad shirt! I love the ruffle sleeves and, best of all, it even has pockets. Check it out here.

---

Aloha Pineapple T-Shirt

This t-shirt is perfect for vacationing in Hawaii. The t-shirt spells aloha down the front of the tee. The best part is the o is a pineapple, how cute is that! Check it out here.

---

Shop our Ladies Pineapple Hawaiian Shirt Picks

---

Kid’s Pineapple Hawaiian Shirts

We didn’t leave out the kiddos! We put together below our absolute favorite kid’s pineapple Hawaiian shirts for you to choose from!

---

Girls Pineapple Print Tee

This tee is so cute and stylish, the design has a watercolor style pineapple with the word Aloha on top! Check it out here.

---

Boys Pineapple Surfer Shirt

This t-shirt is so cool for the beach. The design has a pineapple with sunglasses, surfing a wave. How cool is that! Check it out here.

---

Girl Flip Sequin Pineapple Tank Top

This tank top is absolutely fabulous for vacationing. This top has a neon teal color with a flip sequin pineapple on it. Check it out here.

---

Boy’s Colorful Pineapple Shirt

This graphic tee is super cool! We love the colorful look to the pineapple. Check it out here.

---

Kid’s Sunset Pineapple Shirt

This cute yellow sunset pineapple shirt will be the perfect addition to your suitcase! Check it out here.

---

Shop our Kid’s Pineapple Shirts Picks

---

Disney Hawaiian Shirts

You might be wondering how this got to be a category all of its own. Well, Aulani has actually become one of our favorite spots in all of Hawaii. We love getting that taste of Disney magic alongside all the beauty of Hawaii. Here are some pineapple Hawaiian shirts with a Disney twist!

---

Lilo & Stitch Pineapple Hawaiian Shirt

Are you a Lilo & Stitch fan? We love how cute this Stitch Pineapple Hawaiian shirt is! Check it out here.

---

Grogu (Baby Yoda) Pineapple Hawaiian Shirt

THIS IS THE WAY! How can you not buy this adorable Baby Grogu pineapple shirt! I mean, come on, he is hugging a pineapple! Check it out here!

---

Mickey Mouse Pineapple Shirt

We love this cute Mickey Mouse pineapple shirt! Check it out here.

---

Shop our Disney Pineapple Hawaiian Shirt Picks

https://rstyle.me/+NTFHd568qggnwt8qhtnQDg

---

Let us know your favorite Hawaiian pineapple shirt in the comments below!

---

If you enjoyed reading about our pineapple Hawaiian shirt, you may also Like:

Top 5 Mistakes Parents Make When Traveling with Kids

The BEST Swimsuits for Mom [styles for every shape]

3 Simple Tricks to Help You Update Your Kids Wardrobe + Rock Spring Break in Style

BEST HAWAIIAN ISLAND FOR KIDS – AMAZING ACTIVITIES, RESORTS & MORE

21 AMAZING THINGS TO DO IN KONA HAWAII – #6 IS AN ABSOLUTE MUST!

---

Pin-it for later: 15 Perfect Pineapple Hawaiian Shirts for the Whole Family!