Clothes I’ll Never Wear Sailing Again (And What You Should Wear!)
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When we invite new sailors onboard, one of the questions I often get asked is ‘What should I wear?’. It’s a good question, because nothing will ruin your enjoyment more than wearing the wrong clothes for the conditions (I’ve been there, done that!). A fun, sunny day at sea wearing a crop tee and jean shorts can quickly become a miserable time if the wind picks up, and a rainy squall blows through and you end up freezing wet.
There’s an old sailor’s saying: “There’s no such thing as bad weather. There’s only bad clothing.” So what are you supposed to wear? What’s considered ‘good clothing’ for sailing?
I’ll help you figure that out here, so you can be comfortable, relax, and enjoy your time on the water. To start, I’ll show you the type of clothes I’ll never wear sailing again (and why). And I’ll share my outfits for summer and winter, based on my own experience of what works best. The great news is, you’ve likely already got suitable clothing in your wardrobe! It’s just a matter of knowing what to wear.
And if you’re looking for the best shoes to wear sailing, I’ve got you covered there too.
What to wear will depend on where you’re sailing and what season it is.
Cruising in the tropics is quite different to sailing in Norway in winter, or New Zealand. However, I’ve got five golden rules that apply to putting together a sailing outfit that will cover most moderate temperatures — wherever you are.
The 5 golden rules for planning your sailing outfit:
1. Check the forecast and assess the weather conditions.
Planning ahead for the weather will mean you can dress right for the day from the start. That might mean pulling out woollen beanies or wet weather gear the night before.
2. Wear layers.
Sailing involves wind, and combined with ocean spray, it’s often wetter and cooler out on the water than anticipated. The easiest way to stay comfortable is to wear layers so you can warm up by adding extra clothes, or strip off to cool down. Here are the best fleece midlayers to wear.
3. Take spares.
If you’re not living aboard, then having a spare set of dry clothes (or two) with you is a good plan. While there’s usually not a huge amount of space on the boat for clothing, by taking the right clothes, you’ll ensure everything you’ve got is useful.
4. Dress for comfort.
Sailing and living aboard requires that you’re actively mobile and able to move through a range of motions. Being restricted or uncomfortable in clothing isn’t a great feeling — I’ve learned to choose comfort over style.
5. You won’t care what your clothes look like when the going gets rough.
The minute it’s ‘all hands on deck’ and you’re focussed on a sailing task (or if you get seasick!) — the last thing you’ll be thinking about is looking stylish or designer brands. Sailing has a brilliant way of keeping life in perspective — and the priorities start with survival and safety.
Advice on choosing the right clothing fabrics for sailing.
I always recommend wearing natural materials over synthetic ones. Fabrics made from wool, and cotton wear are breathable and more earth-friendly, being biodegradable. Merino wool is excellent as a base layer as it’s soft and comfy and doesn’t hold onto odour or moisture. Cotton, although it doesn’t retain heat when wet, is a great choice for summer t-shirts and long-sleeve shirts as it’s cool and breathable on hot sunny days.
Note: Wind and waterproof layers will typically be made from synthetic fabrics such as GORE-TEX.
Advice on how much to spend on sailing clothes
Some of the brands we recommend are top-end, but I’m a big thrift-store shopper too, so high-quality brands are the ones I’m on the scout for. You’d be surprised what turns up in a second-hand shop! Keep an eye out for second-hand gear at local sailing clubs or in Facebook groups — as there’s often good gear and deals found locally.
If you can’t find what you need second-hand, I encourage you to buy the best clothing and gear you can afford. That is — high-quality materials, made to last gear which is ethically made, by environmentally reputable businesses. It’s better to have a smaller wardrobe of well-made clothing (that you actually like and enjoy wearing!). Clothes at sea get a hard time in in the outdoors, so you want them to be durable and last the distance. The most expensive items, such as good wet-weather gear and sailing boots, are best bought once you’ve committed to the sailing lifestyle.
Clothes I’ll never wear sailing in summer again.
While they’re cool on hot days, (and feel summery) I’ve found floaty dresses and long skirts totally impractical onboard. I’ve tripped climbing up and down the companionway stairs and had to untangle a cord belt snag from the winch. Not to mention having a wet grubby line dragged across my white shorts, and odd marks of all kinds appear (all quicker than a kid's sticky fingers!). And no matter how careful I am, white clothes always attract a stain.
BUT I still have a nice outfit onboard for wearing ashore — I for one, love my sundress and a piña colada on the beach!
Love a good sun dress, but it’s easily snagged while sailing
Long skirts aren’t very practical onboard
An all white outfit is just begging for a stain!
What to wear onboard in summer.
SUMMER CLOTHING
Summer in New Zealand is a mixed bag of wind, rain and sun. The temperature can be anywhere between 60.8°F-89.6°F (16°-32°C). So we’ve always got our windproof jackets and wet-weather gear handy, as well as a swimsuit! It’s super important to protect yourself from the sun and UV damage so a hat is always an essential part of an outfit — see the 5 best sun hat styles for sailing.
Exercise leggings are my go-to for summer cruising for many good reasons. You’ll find they don’t restrict your movement, give sun protection, are easy to clean (and dry) and don’t take up much space. Basically, any athleisure gear such as yoga pants, leggings and shorts will be comfortable to wear for casual sailing in warm weather. Along with these, I’d add more or less merino layers depending on the season.
As you’ll see below, I’ve found a combination of these clothes works well:
Athleisure leggings
Linen and sporty shorts
Merino singlets/tees
Long-sleeve cotton polo shirts (the collar is good neck shade)
Long- sleeve linen shirts (great over swimsuits lounging around)
Wet weather jacket and a good pair of sailing pants (because summer in New Zealand always includes rain!)
My summer outfits
Outfits I wear sailing in summer
Clothes I’ll never wear sailing in winter again.
On one of my first sailing trips, I thought it’d be fine to wear skinny jeans (newbie much?!). Unfortunately, I took a salty/rainy drenching in a squall and spent the rest of the trip wishing I’d worn something different (and a bit more stretchy while sitting for long-periods in the cockpit). While I love my denim, it’s hard to dry out once wet, and then it doesn’t keep you warm.
This denim and white shirt looks great but reality’s different to a photoshoot!
What to wear onboard in winter.
These days in winter, I’ve found it much easier to stay warm, dry and comfortable with a combination of the following clothes:
Merino leggings
Merino singlet
Athleisure leggings & trackpants
Fleece (like these) or Woollen jersey
Puffer jacket
Windproof jacket
Woollen socks and gloves (here’s the best gloves to wear onboard)
Woollen neck gaiter
Buying a sailing jacket to wear in summer and winter is an essential investment if you’re going to be spending time on the water. Read my Easy Guide to Buying the Best Sailing Jacket.
My winter outfits
Outfits I wear sailing in winter
Shop the gear
Gill OS3 women’s coastal sailing jacket
Helly Hansen polo
NINEXIS hoodie
Dale of Norway Rondane Sweater
Icebreaker merino leggings
Carraig Donn merino knit
Icebreaker merino cami
Comfy summer cotton shorts
Ray-ban Clubmaster sunnies — havana
Ray-ban Clubmaster sunnies — mirror blue
Must-haves to wear
Importantly, there’s a couple of essential items to wear which will keep you safe at sea. A lifejacket should always be handy to put on at any time. If you need to buy a life-jacket or PFD make sure you read this guide first, so you choose the right one for you.
And sunscreen will protect your skin from UV damage — it’s important to wear in summer and winter!
A life-jacket is the most essential thing to have available to wear at all times
Protect your skin from UV damage — wear sunscreen, summer and winter
Remember, you’ll never regret choosing comfortable, suitable clothes over something that looks good on shore. No one cares what you look like at sea! The most important thing is that you have fun and wear a smile.
Let me know your favourite go-to sailing clothing below!
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