16 Best Sailing T-Shirts: Look Cool On & Off The Water
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Last Updated on August 26, 2026 by Brendan
Pick a hobby or activity and you will be able to find a complete line of t-shirts to match. Sailing t shirts are no exception.
Sailboat t-shirt choices range from casual, funny, and practical with such messages as “I’d Rather Be Sailing” and “Life is Simple. Eat, Sleep, Sail”.
The complete selection of sailing t-shirts includes styles and designs for women, men, and kids. So there are plenty of reasons to enjoy your time in the sun, on or off the water, and still be able to share your love of sailing with a t-shirt that does the talking for you.
If you want to get some ideas for the different styles of shirts for sailing on the market, have a look at our favorite ones below.
Or for more shirts and jackets for sailing, click here.
The Best Sailing T-shirts We’ve Found
Check out our picks of the best sailing t-shirts below…
Evolution of the Sailor Sailing T-Shirt
Key Specs
| Manufacturer | Evolved Sailor Apparel |
| Sizes | XS, S, M, L, XL, XXL, 3XL, 4XL, 5XL, 6XL |
| Colors | Black, Navy Blue, Red, Green, Royal Blue |
| Fit Type | Men, Men’s Big & Tall, Women, Women’s Plus, Youth |
| Machine Washable | Yes |
| Material | Cotton, Cotton/Polyester |
This “Evolution of the Sailor” T-shirt is unique and displays a short history lesson. The design features a chronological progression of sailboats through several historic periods. In addition to showing a glimpse of the evolution of maritime technology, it also inspires nostalgic feelings for the “good ole days” of sailing. If you have an appreciation for history and the sea, this t-shirt is a must-have in your closet.
I’d Rather Be Sailing T-SHIRT
Key Specs
| Manufacturer | Sailing Tee Shirt |
| Sizes | S, M, L, XL, XXL, 3XL, 4XL, 5XL, 6XL |
| Colors | Black, Asphalt Grey, Red, Kelly Green, Royal Blue |
| Fit Type | Men, Men’s Big & Tall, Women, Women’s Plus, Youth |
| Machine Washable | Yes |
| Material | Cotton, Cotton/Polyester |
This is a classic! The “I’d Rather Be Sailing” T-shirt highlights a simple but direct statement. It offers a solution to the question, What would you rather be doing right now if you could be doing something else? If you have a passion for sailing, this t-shirt allows you to share that without conversation. Give others a sense of what is really on your mind with this bold declaration of something better to do.
The Captain Is Always Right and I’m The Captain T-Shirt
Key Specs
| Manufacturer | Funny Boat Captain – Clothing |
| Sizes | S, M, L, XL, XXL, 3XL, 4XL, 5XL, 6XL |
| Colors | Black, Navy Blue, Asphalt Grey, Slate Grey, Cranberry Red |
| Fit Type | Men, Men’s Big & Tall, Women, Women’s Plus, Youth |
| Machine Washable | Yes |
| Material | Cotton, Cotton/Polyester |
If you have a sense of humor and want to share it, then a t-shirt that states, “The Captain Is Always Right and I’m the Captain” pretty much sums it up and cuts directly to the point in a tongue-in-cheek manner. Captains and their crew have mutual respect for the roles each play, but that doesn’t mean they don’t have time for playful messages like this one. Share your authority with a smile.
Women’s I’d Rather Be Sailing T-Shirt
Key Specs
| Manufacturer | AM T-Shirts |
| Sizes | S, M, L, XL, XXL |
| Colors | Black, Pink, Red, White |
| Fit Type | Classic Feminine Fit |
| Material | Cotton |
This is a variation of the classic “I’d Rather Be Sailing” T-shirt but this one is designed for women. The bold and straightforward statement indicates that the message of being somewhere else doing something enjoyable on water transcends gender. After all, sailing is an activity that can be enjoyed by all, young and old. This t-shirt is shaped and cut differently to fit the female form and says it like it is.
What Happens On the Boat Stays On the Boat Short Sleeve T-Shirt
Key Specs
| Manufacturer | ThisWear |
| Sizes | S, M, L, XL, XXL, 3XL, 4XL |
| Colors | Ash, White, Light Blue, Sport Grey |
| Material | Cotton |
Witty and light-hearted are words used to describe the message that appears across the front of this “What Happens On the Boat Stays On the Boat” T-shirt. It features short sleeves giving it a casual look with wording that indicates you’re in a safe place. Not that things will purposely get out of hand, but in case something happens, your secret is safe. At least that’s the point of the joke here.
Retro Striped Ladies Sailing T-Shirt
Key Specs
| Manufacturer | Buzz Shirts |
| Sizes | S, M, L, XL, XXL |
| Color | White |
| Fit Type | Ladies-fit |
| Machine Washable | Yes |
| Material | Cotton |
Featuring a classic sailboat image and a vibrant multi-colored stripe, this “Retro Stripes Ladies Sailing T-Shirt” is a perfect choice for the ladies. The t-shirt is designed and cut for women and offers a simple visual scene that brings back memories of spending time on the water. It also beautifully displays the wonder of sailing, and you can just about feel the sea breeze blowing in your hair when see this design.
SAND. SALT. SURF. SUN. Women’s Turtle UPF Performance T-shirt
Key Specs
| Manufacturer | SAND.SALT.SURF.SUN. |
| Sizes | S, L |
| Colors | Yellow, Grey, Pink, Seagrass, Blue, Pink Blossom |
| Fit Type | Men, Women |
These four words paint a vivid picture in the mind of the freedom found simply when near or on the water. This long-sleeved women’s UPF 50+ performance t-shirt says it all. The t-shirt is lightweight and features moisture-wicking technology to keep you cool and dry making it the perfect choice for active pursuits or just to relax in. The turtle image promotes a connection with nature.
Gill Men’s UV Tec Long Sleeve T-Shirt
Key Specs
| Manufacturer | GILL |
| Sizes | XS, S, M, L, XL, XXL, 3XL |
| Colors | White, Charcoal, Navy, Medium Grey, Ocean |
| Fit Type | Regular fit |
| Machine Washable | Yes |
| Material | Polyester |
There is a lot of function and design in this “Gill Men’s UV Tec Long Sleeve T-Shirt.” It includes a zip-up feature with a collar and 50+ UV protection that will keep you from getting burnt in the sun. It is because of these features that this T-shirt is suitable for various activities that do not require a boat or water. The tee comes with moisture-wicking technology and is made from quick-drying material which will keep you cool and dry.
Nautical Heartbeat Short Sleeve T-Shirt
Key Specs
| Manufacturer | Cool Vintage I Love Sailing Design T-shirts |
| Sizes | S, M, L, XL, XXL, 3XL, 4XL, 5XL, 6XL |
| Colors | Black, Navy Blue, Asphalt Grey, Slate Grey, Royal Blue |
| Fit Type | Men, Men’s Big & Tall, Women, Women’s Plus, Youth |
| Machine Washable | Yes |
| Material | Cotton, Cotton/Polyester |
The “Nautical Heartbeat Short Sleeve T-Shirt” is a short-sleeved t-shirt featuring a heartbeat and a sailboat image. It is a visual representation of a deep connection to the sea. It displays the rhythm of sailing with waves intertwined with the heartbeat. If you have such a strong passion for sailing that you truly feel it with all your heart, this T-shirt will help you to express that clearly to everyone.
Helly-Hansen Women’s T-Shirt
Key Specs
| Manufacturer | Helly Hansen |
| Sizes | XS, S, M, L, XL, XXL |
| Colors | Navy, Dusty Syrin, White, Cream Esra Print, Festival Fuchsia, Snow, Melon, Azalea Pink, Red, Oxblood, Alert Red, Sunny Lime, Midnight Green Esra Print, Spring Bud, Cornflower, Royal Blue, Teal, Glacier Blue, Nimbus Cloud Melange, Grey Melange, Pink Sorbet |
| Fit Type | Regular fit |
| Machine Washable | Yes |
| Material | Cotton |
The “Helly-Hansen Women’s T-Shirt” is a classic must-have! The lightweight, 100% cotton single jersey fabric construction is comfortable and contemporary. It’s also stylish in a way that only Helly-Hansen can produce. The tee also features a large “HH” logo on the chest to make the branding loud and clear. The logo speaks to the history and quality associated with this activewear manufacturer.
Yes, I Have A Retirement Plan Sailing T-Shirt
Key Specs
| Manufacturer | Retirement Plan Fun Gift Design Idea |
| Sizes | S – 6XL |
| Colors | Various colors |
| Fit Type | Men, Women |
| Machine Washable | Yes |
| Material | Cotton, Cotton/Polyester |
It’s a short-sleeved t-shirt with “Yes, I Have A Retirement Plan” displayed across the front. If you like tees that have a witty, aspirational message, you can’t go wrong with this choice. It has both of those and celebrates the rewards available to sailors once they reach retirement age. The message clearly captures the essence of the dream that many of us want to experience at some point in our lives.
If You Can Read This I have Capsized T-Shirt
Key Specs
| Manufacturer | CrystalPrint |
| Sizes | S, M, L, XL, XXL, 3XL, 4XL, 5XL, 6XL |
| Color | Black |
| Fit Type | Men, Men’s Big & Tall, Women, Women’s Plus, Youth |
| Machine Washable | Yes |
| Material | Cotton, Cotton/Polyester |
What makes the joke found on the “If You Can Read This I Have Capsized” T-shirt even funnier is that the text is printed upside down. It’s a clever spin on the sense of humor sailors must possess on those sailing days when things just don’t go quite according to plan. After all, there isn’t a single sailor on the water who intentionally plans to capsize, but it happens, and finding humor in the situation can soften the blow.
Nautica Men’s Short Sleeve Performance Polo Shirt
Key Specs
| Manufacturer | Nautica |
| Sizes | S, M, L, XL, XXL, 3XL |
| Colors | Bright Cobalt, Bright Cobalt/Nautica Red, Bright White, Nautica Red, Navy |
| Fit Type | Classic Fit Men |
| Machine Washable | Yes |
| Material | Cotton, Cotton/Polyester |
If you are seeking a stylish, functional shirt that can be worn in various settings because of its classic look, then look no further than this “Nautica Men’s Short Sleeve Performance Polo Shirt.” It comes complete with a vented hem, moisture-wicking fabric, and iconic graphics that will make you look like you fit in wherever you wear it. It’s also the perfect shirt to wear when sailing the open seas dreaming of a perfect day on the water.
Helly Hansen Men’s Riftline Polo Tee
Key Specs
| Manufacturer | Helly Hansen |
| Sizes | XL, 4XL |
| Colors | White, Am Sup White, Alert Red, Navy, Grey Fog, Red, Olympian Blue, Black, Factory, Ebony |
| Machine Washable | Yes |
| Material | Polyamide |
Style and function are the keys behind the “Helly-Hansen Men’s Riftline Polo Tee.” It features a short-sleeve design and high-quality fabric in the classic construction that the brand is well-known for. The fit is perfect and with the classic “HH” logo, you know you are wearing something with a strong background in activewear. If looking good when having fun is important to you, this polo tee will do the job and do that job well.
Altered Latitudes Men’s Laser Olympic Class Sailboat UPF Long Sleeve T-Shirt
Key Specs
| Manufacturer | Altered Latitudes |
| Sizes | XS, S, M, L, XL, XXL. 3XL, 4XL |
| Colors | Columbia Blue, Salmon, Seagrass, White, Athletic Grey, Tan |
| Fit Type | Classic Fit Men |
| Material | Microfiber |
If laser dinghy sailing is your thing, then you will want to add this “Altered Latitudes Men’s Laser Olympic Class Sailboat T-Shirt” to your collection. It has long sleeves, features UPF 50+ sun protection, and is constructed from lightweight, breathable, comfortable fabric. It also has moisture-wicking technology to keep you cool and dry under any condition. The design captures the feel and excitement of competitive laser sailing.
Helly-Hansen Men’s Tech Crew Sailing Shirt
Key Specs
| Manufacturer | Helly Hansen |
| Sizes | XS, S, M, L, XL, XXL. 3XL |
| Colors | Ebony, Light Grey, White, Navy |
| Fit Type | Regular fit |
| Machine Washable | Yes |
| Material | Polyester |
For the active man, you can’t miss with the “Helly-Hansen Men’s Tech Crew Sailing Shirt.” It is made from quick-drying, moisture-wicking material that offers function with a style that keeps you comfortable and looking good. The shirt features long sleeves for sun protection and offers a perfect fit that gives you room to move around easily. Plus, it comes from a brand that has a noted history of producing quality and functional activewear.
Conclusion
So there you have it… our favorite sailing t-shirts. But we know there are literally thousands of different t-shirt designs out there… the choices are limitless.
Have you got a favorite sailing t-shirt? What’s your pick? Share a link to a picture or just the quote here for all to enjoy!
