The Best Sailing Clothing for Men and How to Dress for Your Next Outing

Ahoy there! The summer season is fast approaching, and with it comes the perfect weather for sailing out on the open water.

Whether you prefer to take the boat out with the guys or make it a family adventure with your partner and kids, you need to make sure you are wearing the appropriate clothing for the occasion.

While it is important to dress practically for all that you need to do on and around the boat, you should not have to compromise on style.

Fortunately, Castaway Nantucket Island clothing provides items that fit the bill for both functionality and fashion for the days spent out on the water.

Today we will look at some of the best sailing clothing for men and how to dress appropriately for your next outing.



The act of fishing really is an ancient one, as it dates back at least tens of thousands of years.

It started as a primary method of gathering food and is still definitely used for this purpose. Still, now it is also considered a popular pastime, especially for those who enjoy being out on a boat.

And why would it not be? It does not require a lot of equipment. It is easy to get started, and, if you are lucky, it can even provide you with your dinner for the night!

Perhaps best of all, it is a casual sport that you can engage in with just about anyone, from your friends to your partner to your kids.

If you prefer to sail on your own to take full advantage of the peace and quiet that being out on the water can offer, dinghy sailing can also be a perfect solo activity.

While it certainly can be a relaxing way to spend your time out on the boat, it can also be quite time-consuming if you are determined to make a catch and the fish just are not biting that day.

Let us look at some of the sailing clothes that would be appropriate for those fishing-related sailing outings.


The Best Sailing Clothing for Fishing


Since you may be spending a lot of time out on the water trying to get a bite, the best sailing clothing for men for this occasion would consider the changing temperature throughout the day.

If you start at dawn, as this is arguably one of the best times to fish, you may consider a quarter zip sweatshirt with a fleece interior to help keep you warm until the temperature starts to increase later in the day.

As you start warming up, this can easily be pulled off to reveal a classic and comfy T-shirt underneath. Either of these basic types of tops can be paired with a pair of embroidered sailing shorts to show off your love of fishing in style.


If patterned sailing shorts are not really your thing, but you still want to add a little bit of fun to your outfit, you may want to pair a more neutral short with a fishing-themed belt. Another accessory that may be useful to the sailing fisherman is a hat such as a visor to help protect their eyes from the sun as they keep an eye on their line.

Complete this look with a pair of waterproof boat shoes so you can stand up in the sailboat to reel in a big one without worrying about slipping on the deck. Note that it is important to ensure you are wearing closed-toe boat shoes instead of sandals or going barefoot.

If you are barefoot while boating, you may be more likely to slip on the deck, and sandals may slip off your feet entirely if the sailboat has gotten especially slick with water. Proper footwear is essential for keeping yourself safe while boating.



Man overboard! Considering you are surrounded by water, perhaps the most obvious activity to engage in while sailing is swimming.

Whether you are playing around with others or just going for a dip to cool off after being in the sun all day, swimming can be a great activity to get your body moving after being on a boat for a long period of time.

A towel for drying off and sunscreen for your face and body are, of course, necessities to bring on the boat when you know you will be swimming, but what kind of clothes should you wear for both in and out of the water?

Now let us consider the best sailing clothing for men when you know swimming will be a major part of your outing.


The Best Sailing Clothing for Swimming


When considering the best swimming-related sailing clothing for men, especially when you are not planning on bringing a lot of extra clothes, it is important to pick items that are fashionable and functional both in and out of the water.

The number one thing you will need, of course, is some type of swimsuit.

Not only does this pair of trunks come in a pattern to show off your love of sailing, but they are also quick-drying, which means you will not be stuck in wet shorts all day if you find yourself in and out of the water often on your sailing adventure.

When you do come out of the water, you will want to keep yourself protected from the sun, so this sun shirt with a cool graphic and solar protection of UPF 50+ is a perfect choice.

This type of shirt is also moisture-wicking, which means that if it does get wet from either water or sweat, it will help keep you relatively dry.

If you tend to get cold fairly quickly after coming out of the water, this lightweight popover hoody can warm you up without making you too hot in the sun.


As for accessories for the swimming sailor, the best choices are those that offer additional sun protection. Sunglasses are a must for keeping your eyes shielded from those rays, and if you find yourself taking them on and off all day long, you may consider wearing them with a Croakie.

This way, you can keep them handy around your neck throughout your journey, and if they do happen to fall into the water, this accessory is guaranteed to float – you do not want to take any chances with an expensive pair of sunglasses!

When you are out of the water in between dips, a baseball cap can provide additional protection from the sun for both your head and eyes, especially if sunglasses are not really your thing. Available in many colors, you can find a cap to match any sailing outfit.


Date Night

A day or night out on the water can be the perfect setting for a romantic date with a loved one. You can sail out to a point where no one else is around and spend time talking and cuddling with your partner in peace and quiet.

While this is a great choice for a day date, an evening sailing adventure can be even more ideal. Observing a sunset together or even being under the moon and stars can provide the perfect romantic atmosphere.

If you are looking to impress your date while sailing, you will want to look your best for them while still easily getting around the boat. Let us now get into the best sailing clothing for men on date night.


The Best Sailing Clothing for Men on Date Night


On date night, you will likely want to dress up a little more than you usually do for your average day on the boat.

If you are going out in the evening or later (which, again, is highly encouraged for the best romantic atmosphere), you may also want to cover up a bit more as the temperature starts to fall.

Therefore, you may want to choose a classic pair of pants for more of a dressed-up look.

Try and go for a pair with stretch and flexibility if you want to be able to still move around the boat easily to show off your sailing skills.

To keep this classic and polished look for your date, these would go well with a collared button-up shirt. A material like linen would be great for those cooler summer nights out on the water, as it will help keep you covered up while still being breathable and lightweight.


To complete the look, again, a pair of sleek and stylish waterproof boat shoes are the perfect choice to keep you from slipping when you are getting around the boat. If your outfit is otherwise fairly neutral, an embroidered belt is a good way to add an extra pop of color and flair.

Finally, while it is not really an accessory, it may be a good idea to bring along a blanket so you can cuddle up with your date in the cooler evenings as you watch the sunset or hang out under the moon and stars.


General Tips When Choosing Sailing Clothing for Men

Nearly all the above options share a few important things in common: they are stylish while still very functional.

A sailor needs to get from point A to point B on his boat quickly and efficiently to do everything necessary to keep themselves on track and afloat.

The nice thing about the clothing provided by Castaway Nantucket Island is that these items are fashionable and practical while also being very comfortable.

They are also available in neutral and bright colors that mix and match well together, so do not shy away from adding a pop of color into your wardrobe.

As a bonus, if you fall overboard or get lost at sea, you will likely be easier to find if you are brightly colored!

In fact, nautical style stripes were originally designed for sailors in the past as they would make them easier to find if they did fall into the water.

This type of pattern is still very much in style today when it comes to sailing clothes for men, especially when paired with a neutral, so if it is a look that appeals to you, then go for it!

 Today we have looked at the best sailing clothes for men and how to dress for your next outing, whether you are looking to fish, swim, or have a romantic night out with a partner.

Please look at the Castaway Nantucket Island website for more styles and items that would be suitable for your next sailing adventure. Bon voyage!

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