9 Sailing Outfits for any Season and Reason no texting & tacking

This post has ideas and photos to help you pack for your next sailing adventure. In hot, or cold weather. Whether it’s a sailing vacation, fishing trip, or a liveaboard experience.

Having sailed in both freezing and hot weather, with three kids (one of them a teen who can never have enough clothes…), we have figured out what works aboard.

We have also made a bunch of mistakes, while living on two sailboats. I am sharing some, so you can avoid them.

As always, this post has been written with no AI involvement. Our experiences carry the true value, for you.

Our Boat Gear page contains tons more useful items.

Sailing Outfit Ideas by Occasion.

Whether sailing for a few days, on a fishing trip, or you plan to live aboard, here are some smart and easy sailing outfits.

a woman on a boat wearing a pink Columbia sun shirt

Any of the outfit ideas below will work for a variety of occasions. I have organized them to make it a bit easier to pack.

1. A Week of Sailing

How awesome!

You must have been planning this trip for a while. Don’t let poor clothing choices ruin the experience.

a man and a woman at Chub Cay, wearing sunglasses

Here are ideas to maximize your wardrobe potential on the high seas:

2-3 bottoms to easily coordinate with any top.
5-6 shirts / undershirts
2 light, loose shirts to use as a cover-up.
Wind breaker / waterproof jacket.
Land shoes (travel in these)
Boat shoes (or go barefoot, if hot).
Sunhat, sunglasses (featured below).

Keep all undershirts light and thin. Check if laundromats will be available.

Try to make all bottoms coordinate with any top, in case of spills, or unexpected splashes.

Shorts are OK aboard, but if sailing in the tropics, you will need excellent sun protection.

Whenever we sailed, I preferred longer, flowy pants. For shade and air flow. The rest of the crew were big fans of shorts.

Note: The captain is required to have reliable life jackets for every person aboard. If you need special size, ask about them.

2. A sailing passage (2-3 days long)

If sailing without stopping, for 2-3 days, you want something super comfortable, stretchy and breathable.

a man on a sailboat wearing a long sun shirt, short and a hat, swinging on a swing

Why 2-3 days? It is what is needed for the body to adjust to the motion and not feel seasick any longer. So, the first couple of days are the hardest.

Chances are you will be seasick, and you might not be feeling your best.

Worried about seasickness? I have just the two posts for you:

Seasickness Sucks – 21 Tried and Tested Tips to Stop it.

10 Seasickness Questions – Answered (by a Boat-mom).

Whenever we started a passage, I would change into some sort of yoga pants and a t-shirt. I would have a light sweater and a windbreaker available in the salon, so I would not have to go downstairs into the cabins, at all.

Tip: Pick an outfit, which will allow you to lie down, walk around and, hate to say it, throw up overboard, if you must.

3. Land and Sail trip

How about a day sail and a local market trip, or an island hiking?

Sail into something comfortable, that can dry easily if splashed. If planning on wearing nice clothes on land, I’d change right before that.

Trust me, even a short sailing trip can make you seasick, you need comfortable attire aboard.

Tip: If wearing boat shoes, please leave them aboard and change into your street shoes. Be considerate. Take the street shoes in a bag and change ashore.

4. All-hands-on-deck outfit

If expected or hoping to be helping aboard with lines and boat handling, put on your exercise outfit, rather than the lounging photoshoot dress.

Guys are a bit easier, mostly because they don’t care much.

Having said that, if you are curious to peek into the engine compartment, help with the anchor, or handle tools, you might get diesel and dirt on your clothes. Just FYI.

If helping aboard, you need to be either barefoot, or in boat shoes. You need excellent grip, which regular street shoes will not provide.

Don’t run around on deck in flip-flops. There are boat parts, lines, cleats, countless tripping hazards.

Any boat surface not covered with an anti-slip coating is very, very slippery when wet. Here is a helpful post about what shoes are OK to run around in:

Comfortable Sailing Shoes for Every Boating Need

You should not be expected to climb anything, while underway, apart from possibly helping with the main sail, depending on the boat layout. We left all mast excursions for the calm bays.

Note: The captain is required to have reliable life jackets for every person aboard. If helping out, on deck, you’d want one on.

5. Fishing trip

Going fishing for the day?

Make sure you catch the big one.

In the meantime, wear your fish-friendly clothes. Meaning, anything you can get fish slime on.

If fishing, you will be spending a long time outside, hopefully under shade of some sort.

Ideally, wear a long sleeve shirt the entire time. A light cotton shirt will do too.

Even more important, depending on the type of boat, you might need a pair of boating boots. I have some cool ideas in this post.

Comfortable Sailing Shoes for Every Boating Need

Here is a good post with some gifts for fishing boaters, while on the topic:

51 Gifts for Boaters. Ultimate Guide (Cruisers Approved)

Tip: Don’t forget your hat and sunglasses (the polarized ones).

Liveaboard Life

If living on a sailboat, wise use of space is crucial.

Having said that, you will have access to marinas with laundromats, even if you do not stay at a slip.

For more liveaboard gear:
My Composting Toilet Aboard – Love-Hate Relationship (Pros and Cons).
My Washing Machine Aboard – Forget Bucket Laundry!
19 Best Boating Bags. Tips How to Use Them.
Comfortable Sailing Shoes for Every Boating Need
27 Perfect Books for Boaters.

You might have a washer aboard too (I did, and cannot sing enough praises to it).

Actually, here are a few: My Washing Machine Aboard – Forget Bucket Laundry!

Here is what to keep in mind, when packing to move aboard:

Have plenty of old shirts and shorts – boat repairs happen all the time.
Buy all of your specialized sailing clothes and boat gear while still on land.
Buy all of your rash guards before you sail off.
Leave all jeans, leather and down jackets on land.
Leave everything with metal zippers on land (including bags).
Leave wool sweaters, bring fleece aboard.
You can find any piece of clothing abroad.

Tip: Any of the outfits listed here will be suitable for daily liveaboard life. But you have a lot of time to switch things around. Don’t overthink it.

What to wear when it’s hot.

Think light and airy, rather than short and tight. Longer flowy pants and a loose sun shirt will keep you far more comfortable, than jean shorts and a tank-top.

a man at the helm of a sailboat, with blue green water and a city behind him

6. Basic Stay-Cool Outfit

Even in hot weather, layering works.

Stay away from dark colors, because you will be very hot.

Here is an idea for a basic sailing outfit, for the tropics:

Light, flowy shirt or
Any top and a light long-sleeve beach cover-up
Loose yoga or gym shorts (if you prefer shorts)
Flowy pants, if you prefer pants.
Mid-length sun dress/skirt.
Sun hat
Sun glasses
Sailing shoes or barefoot.

Don’t forget your feet. They are very easy to burn and it hurts.

Tip: You will be sunburnt quickly, and you might not notice it, because the breeze aboard will keep you feeling cool. Cover your body or use sunscreen.

Hot Weather Tops

Sun shirts are ideal for sailing. They allow plenty of air and protect from the strong sun.

Cotton, once washed and a dried a few times, has some UV-rays protection (not much).

I am not a fan of plastic, but synthetics dry a lot faster and are easier to fit inside a small washer aboard. We did laundry every other day, it’s inevitable, with 5 people aboard.

You can also wear regular tank tops, or t-shirts and cover your shoulders with a light sun shirt, or cover-up.

Tip: A beach wrap is perfect for the beach, not for sailing. Your hands must be free to grab onto the boat, while cruising. The less loose fabric waving in the wind and getting caught in steel ropes and lines, the better.

Hot Weather Bottoms

Synthetic, airy, flowy.

For guys, gym shorts or long sun pants are perfect. They pack small, are easy to wash and dry very quickly.

For girls, mid-length flowy pants and skirts are perfectly fine aboard.

Shorts were practically uniform for my teens, while we lived on a sailboat, but I cringed every time a saw a pair of jean shorts in the washing machine. No matter how many times I skillfully tucked them away in a drawer, they reappeared…

Hot Weather Shoes

We ran around barefoot all the time. You do not need any shoes aboard, if sailing in hot weather.

Having said that, sometimes you will want to protect your feet and for added comfort.

Check out my very detailed post about sailing and boating shoes, you will get a good idea about what to wear.

Comfortable Sailing Shoes for Every Boating Need

What to Wear when it’s cold.

In a way, hot weather sailing outfits are trickier.

a woman wearing a jacket, hat and harness on a sailboat

Cold weather outfits allow for layering and the long sleeves and pants naturally add the sun protection.

7. Basic Stay-Warm Outfit

Here is a good basic outfit, which you can combine with anything:

Leggings, yoga pants.
Waterproof / windbreaker pants.
Long-sleeve undershirt.
Fleece shirt to layer.
Waterproof / windbreaker jacket.
Sailing shoes
Hat and sunglasses

Cold Weather Tops

While sailing in cold climate, expect cold and windy combo.

All the time.

Layering is ideal, so start with something comfortable, thin and tight. A long-sleeve undershirt is best.

You can change undershirts more often. So, keep a couple of fleece sweaters aboard and don’t worry about washing and drying these as often.

Always have a good waterproof jacket near-by.

Tip: Stay away from puffy jackets and definitely no down parkas and such. They are impossible to hang to dry, if they get wet.

Cold Weather Bottoms

Again, layering is key.

Keep a pair of leggings (long underwear) as a base layer. Then put on a pair of waterproof pants on top.

Pack a few pairs of leggings, they are easy to change daily.

When we started our liveaboard life, it was below-freezing outside. I made every mistake I am warning against. We ended up donating and driving back quite a few heavy pants and sweaters.

Tip: Stay away from anything down, heavy and jeans.

Cold Weather Shoes

Think comfort and protection, for your feet and for the boat.

Check out my detailed post about picking out the best pair of sailing and boating shoes.

Comfortable Sailing Shoes for Every Boating Need

What to pack for the kids.

If sailing with kids, you might need to pack for them, or at least inspect what they plan to bring aboard.

three kids facing the ocean wearing sunhats

8. Great Outfits for a hot sail.

Younger kids are very active aboard. They will want to spend a great deal of time outside.

And they should, otherwise they will be seasick (read all about kids and seasickness in my post: Seasickness Sucks – 21 Tried and Tested Tips to Stop it.

Have them wearing something light, and in light colors.

Here is an easy idea:

Sun shirt. Long sleeves are fine, the breeze will keep them cool.
Shorts, or mid-length pants
Sun hat and sunglasses (if they’ll keep them on).

Do insist on a hat outside and put sunscreen on their feet (easily forgotten).

Tip: Change out of the bathing suits once done swimming. Fungal infections are common in tropical climates.

9. Great outfits for a cold sail.

A basic long under-wear shirt and pants is easy to pack and easy to wash, and dry.

Leggings / long underwear pants
Long-sleeve shirt / long underwear shirt
Sweat pants
Fleece top
Waterproof windbreaker

Kids should have waterproof jackets aboard, but they are mostly used as a windbreaker, and for shore trips.

They will also need to be a reliable life jacket every time they are out on deck.

Note: Young kids have no business outside in rough weather, so they do not need special waterproof pants or foul weather gear.

Must Have Accessories

Regardless of the season, these must be always with you aboard.

a woman at a tropical island in a summer outfit

Sun Hat

A sailing hat must have a wide brim and a soft, comfortable strap.

Fabric hats are best, because they can be folded for easy packing and can be washed and dried.

Tip: Expect resistance from the kids. Stay strong.

Polarized Sunglasses

Any type of biking, polarized sunglasses will do.

I bought Joe a pair of Oakley’s and made sure they were not left in random places (because captains tend to do that with their tools and belongings). They are a bit expensive, but he has been wearing them for years.

Tip: No matter the brand, look for good around-the-eyes coverage:

Face Cover

A light face cover will protect you from the sun and the wind. In any weather.

If going on a brief sailing trip, not having a face mask is not a big deal. But if you have one anyway, take it along. They are very light and versatile.

We have five of them and had them aboard as well as on the ski slopes:

Tip: Face covers will make perfect stocking stuffer, or gifts for boaters.

Sailing Gloves

If you are planning on helping sail the boat, a pair of sailing gloves can be a palm saver.

Especially, if you have not handled a boat before, those sails pack a ton of force and before you know it, a line might burn through your skin.

Note: Always follow the captain’s directions and be fully aware of what’s happening around you.

Glasses strap

Your sunglasses (and prescription glasses) can be blown right off of your face into the water.

Buy a strap. That’s all.

Bags and luggage

Now that we have gone over what to pack, let’s cover bags and luggage.

I have just the right post all about various boating bags:

19 Best Boating Bags. Tips How to Use Them.

Traveling luggage

Please, do not bring hard suitcases aboard. They are very difficult to store.

Your favorite soft luggage carrier will work just fine. Bonus points, if it can be folded.

We love traveling with light backpacks. They carry a lot and the bag itself is not heavy, and can be folded and stored away.

Tip: Hiking backpacks are heavy. Ours came from the hunting section at Decathlon – think outside the box.

Day Bag

If going on a sailing vacation, any day-bag will work. You might have to put it in a plastic bag, during rides to shore.

No need to buy special bags just for a week, or two.

If you want a versatile, waterproof bag, get a dry bag. They are also very light to fly with.

We had 5, or 6 aboard, in various sizes. They kept our medications, belongings gadgets, and have been thrown into waterfalls as well.

Again, here is the post all about boating bags:

19 Best Boating Bags. Tips How to Use Them.

Tip: it might be best to leave your leather bag at home. Salt water is terrible for leather and a sailing trip presents countless opportunities to get splashed.

Do not wear while sailing!

Sometimes it is easier to list what not to wear aboard.

Sophie crocheted this adorable winter set as a gift – a perfect land gift that is. Here is a great post all about gifts for boaters (while on the topic).