16 Best Sailing T-Shirts: Look Cool On & Off The Water

Last Updated on December 5, 2023 by Brendan

Evolution of Man Sailing T Shirts
Men’s Evolution of Man Sailing T-Shirt

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

Dressdown Men's Evolution of Man Sailing T-Shirt - 10 Colours

Key Specs

ManufacturerEvolved Sailor Apparel
SizesXS, S, M, L, XL, XXL, 3XL, 4XL, 5XL, 6XL
ColorsBlack, Navy Blue, Red, Green, Royal Blue
Fit TypeMen, Men’s Big & Tall, Women, Women’s Plus, Youth
Machine WashableYes
MaterialCotton, 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.

Amazon Button

I’d Rather Be Sailing T-SHIRT

I'd Rather Be Sailing T Shirt

Key Specs

ManufacturerSailing Tee Shirt
SizesS, M, L, XL, XXL, 3XL, 4XL, 5XL, 6XL
ColorsBlack, Asphalt Grey, Red, Kelly Green, Royal Blue
Fit TypeMen, Men’s Big & Tall, Women, Women’s Plus, Youth
Machine WashableYes
MaterialCotton, 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.

Amazon Button

The Captain Is Always Right and I’m The Captain T-Shirt

The Captain Is Always Right and I'm The Captain T-Shirt

Key Specs

ManufacturerFunny Boat Captain – Clothing
SizesS, M, L, XL, XXL, 3XL, 4XL, 5XL, 6XL
ColorsBlack, Navy Blue, Asphalt Grey, Slate Grey, Cranberry Red
Fit TypeMen, Men’s Big & Tall, Women, Women’s Plus, Youth
Machine WashableYes
MaterialCotton, 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.

Amazon Button

Women’s I’d Rather Be Sailing T-Shirt

Women's I'd Rather Be Sailing T-Shirt

Key Specs

ManufacturerAM T-Shirts
SizesS, M, L, XL, XXL
ColorsBlack, Pink, Red, White
Fit TypeClassic Feminine Fit
MaterialCotton

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.

Amazon Button

What Happens On the Boat Stays On the Boat Short Sleeve T-Shirt

What Happens On The Boat Stays On The Boat T-Shirt

Key Specs

ManufacturerThisWear
SizesS, M, L, XL, XXL, 3XL, 4XL
ColorsAsh, White, Light Blue, Sport Grey
MaterialCotton

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.

Amazon Button

Retro Striped Ladies Sailing T-Shirt

Retro SAILING Strip Ladies T-Shirt

Key Specs

ManufacturerBuzz Shirts
SizesS, M, L, XL, XXL
ColorWhite
Fit TypeLadies-fit
Machine WashableYes
MaterialCotton

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.

Amazon Button

SAND. SALT. SURF. SUN. Women’s Turtle UPF Performance T-shirt

SAND.SALT.SURF.SUN. Women's Turtle UPF Performance T-shirt

Key Specs

ManufacturerSAND.SALT.SURF.SUN.
SizesS, L
ColorsYellow, Grey, Pink, Seagrass, Blue, Pink Blossom
Fit TypeMen, 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.

Amazon Button

Gill Men’s UV Tec Long Sleeve T-Shirt

Gill Men's UV Tec Long Sleeve Zip Sailing T-shirt

Key Specs

ManufacturerGILL
SizesXS, S, M, L, XL, XXL, 3XL
ColorsWhite, Charcoal, Navy, Medium Grey, Ocean
Fit TypeRegular fit
Machine WashableYes
MaterialPolyester

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.

Amazon Button

Nautical Heartbeat Short Sleeve T-Shirt

Heartbeat Sailing T-Shirt

Key Specs

ManufacturerCool Vintage I Love Sailing Design T-shirts
SizesS, M, L, XL, XXL, 3XL, 4XL, 5XL, 6XL
ColorsBlack, Navy Blue, Asphalt Grey, Slate Grey, Royal Blue
Fit TypeMen, Men’s Big & Tall, Women, Women’s Plus, Youth
Machine WashableYes
MaterialCotton, 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.

Amazon Button

Helly-Hansen Women’s T-Shirt

Helly-Hansen Women's Sailing T-Shirt

Key Specs

ManufacturerHelly Hansen
SizesXS, S, M, L, XL, XXL
ColorsNavy, 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 TypeRegular fit
Machine WashableYes
MaterialCotton

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.

Amazon Button

Yes, I Have A Retirement Plan – I Plan to Go Sailing T-Shirt

Yes I Have A Retirement Plan Go Sailing T-Shirt

Key Specs

ManufacturerRetirement Plan T Shirts
SizesS, M, L, XL, XXL, 3XL, 5XL, 6XL
ColorsNavy Blue, Asphalt Grey, Cranberry Red, Dark Heather Grey, Royal Blue
Fit TypeMen, Men’s Big & Tall, Women, Women’s Plus
Machine WashableYes
MaterialCotton, Cotton/Polyester

It’s a short-sleeved t-shirt with “Yes, I Have A Retirement Plan I Plan To Go Sailing” 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.

Amazon Button

If You Can Read This I have Capsized T-Shirt

If You Can Read This I have Capsized T-Shirt

Key Specs

ManufacturerCrystalPrint
SizesS, M, L, XL, XXL, 3XL, 4XL, 5XL, 6XL
ColorBlack
Fit TypeMen, Men’s Big & Tall, Women, Women’s Plus, Youth
Machine WashableYes
MaterialCotton, 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.

Amazon Button

Nautica Men’s Short Sleeve Performance Polo Shirt

Nautica Men's Short Sleeve Sailing T-shirt

Key Specs

ManufacturerNautica
SizesS, M, L, XL, XXL, 3XL
ColorsBright Cobalt, Bright Cobalt/Nautica Red, Bright White, Nautica Red, Navy
Fit TypeClassic Fit Men
Machine WashableYes
MaterialCotton, 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.

Amazon Button

Helly Hansen Men’s Riftline Polo Tee

Helly Hansen Men's Riftline Polo T-shirt

Key Specs

ManufacturerHelly Hansen
SizesXL, 4XL
ColorsWhite, Am Sup White, Alert Red, Navy, Grey Fog, Red, Olympian Blue, Black, Factory, Ebony
Machine WashableYes
MaterialPolyamide

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.

Amazon Button

Altered Latitudes Men’s Laser Olympic Class Sailboat UPF Long Sleeve T-Shirt

Men's Laser Olympic Class Sailboat UPF Long Sleeve T-Shirt

Key Specs

ManufacturerAltered Latitudes
SizesXS, S, M, L, XL, XXL. 3XL, 4XL
ColorsColumbia Blue, Salmon, Seagrass, White, Athletic Grey, Tan
Fit TypeClassic Fit Men
MaterialMicrofiber

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.

Amazon Button

Helly-Hansen Men’s Tech Crew Sailing Shirt

Helly-Hansen Men's Tech Crew Sailing Shirt

Key Specs

ManufacturerHelly Hansen
SizesXS, S, M, L, XL, XXL. 3XL
ColorsEbony, Light Grey, White, Navy
Fit TypeRegular fit
Machine WashableYes
MaterialPolyester

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.

Amazon Button

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!

About Brendan

Brendan has over 30 years experience sailing dinghies, yachts, and windsurfers, but has recently started Laser sailing. "I found it difficult to find all the information that I needed when I started sailing my Laser, and I am sure that others have had the same problem. So I combined all the information I could into this website to help other Laser sailors get the most out of this sport. If you have any questions or comments, let me know... I will get back to you as soon as I can."

Leave a Comment