Boat Party & Sailing Outfit ideas

Hi Deborah,

Our neighbors own a boat and have invited my husband and me, plus another couple, to come aboard for drinks, appetizers, and a late afternoon sail. What do I wear to look casual but classy? Thanks, Lynne

Boating - Sail Boat Dress


Hi Lynne,

A happy hour boat ride sounds like a lot of fun! Since you’ll be on the water, a nautical-inspired outfit is always chic. Here are some sailing outfits and tips for what to wear to a boat party.


nautical outfit

1. Wear Nautical Colors

Whether you are going for a slow sailboat ride or a quick motorboat cruise you can’t go wrong wearing traditional sailing flag colors.  Blue, white, black and tan with dashes of bright red, yellow, and green will put you in a relaxed boating party mood and make you look like you have been on the water all your life.



Boating - Green Shorts


2. Keep Clothing Basic but not Boring

You are going to be climbing in and out of the boat, shifting around in your seat, and maybe even getting up to cross the deck in wavy waters. So make it easy and don’t wear anything too fussy or busy like a frilly top, or your favorite silky pants. You need more sturdy basics.

As for accessories – smaller accessories that sit close to the body are best. However, if you want to wear fun earrings, for example, go right ahead, but stay away from too much dangly jewelry which will go flying or get caught in some equipment on the boat. Less is more.

Note: Keeping it simple doesn’t mean keeping it boring. For example, this creamy sweater is quite plain and classic but with the off-the-shoulder neckline; it becomes a sexy little sailing number for a boat party. Tassel earrings and flat lace-up sandals give this outfit style, and the yellow tote adds an energetic punch!



Boat party outfit - blue striped shirt and white jenas styled by Fabulous After 40

3. Have Fun with Stripes

Stripes are the first print that comes to mind when you think of sailing and boating. Paired with your favorite white jeans, this cool stripe button-up shirt oozes chic. Whether you are talking blue and white stripes, black and white stripes, red and white stripes, or multicolored stripes, any stripe will do.  More striped summer outfits here.


4. Carry a Big Straw Tote

A big tote is relaxed looking. (A structured handbag is not!) It’s also very handy to carry everything from a  hat and sunglasses to a towel and swimsuit. A straw or rope tote is especially summery and looks so at home on the lake or at sea.

What to wear on a boat party - Red Nautical shorts and top and deck shoes styled by Fabulous After 40

5. Opt for  Linen

Linen is a favorite summer fabric because it keeps you cool, and even when it gets all rumpled, it still looks classy. Try a linen shirt with nautical shorts for a breezy, sailor-inspired look that is practical and cute too.

Boating Striped Top


6. Wear Appropriate Shoes

There’s no place for heels on a boat so make sure you wear flats. Boat shoes or sneakers are ideal but if you want to wear sandals, then just make sure they have light-colored soles. Black soles are taboo since they scuff the boat deck.



What to Wear Sailing - shorts and a tee and windbreaker styled by Fabulous After 40


7. Arrive Already Wearing Your Swimsuit

If your hosts have hinted at a swim during the boat party, be sure to take along a cute swimsuit. It’s so much easier to arrive with it on, under a pair of shorts. Don’t forget to tuck a pair of panties into your bag for when you dry off.


8. Consider Bringing along a Windbreaker

Weather can change on a dime when you are out boating, and those winds can be pretty chilly at times when you are zipping along in the boat, even on a warm day. Think about rolling up a windbreaker or light coverup and stowing it away in your tote bag. Something colorful and sporty is a fun, casual look for an afternoon boat ride.


9. Bring the Right Hat

The sun can get pretty strong out there on the water so to protect your skin and reduce the chance of the sun bleaching out your hair, take along a snug sunhat that won’t blow away.



Sailing - Blue Shorts

As you are running out the door to get to the pier, don’t forget to grab a pair of sunglasses and some sunscreen. You may want to think twice about taking your best ( expensive) sunnies along. A boat is an easy place for them to get lost or squished. Just saying!


Related topic:

What to wear on a Caribbean Cruise Ship



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4 thoughts on “Boat Party & Sailing Outfit ideas

  1. I like your suggestion to ensure the hat we bring won’t easily blow away since it can be pretty windy out on the water in a boat. My husband and I think it would be a fun adventure to book a charter boat rental for our anniversary coming up at the start of next month. Since this will be a new experience for me, your tips about what to wear are much appreciated!

  2. I appreciate your tips on what to wear to a boating party. I like how you said that you need clothes that have more substantial fabric. My friends are thinking of going on a boating activity sometime soon. Having suitable clothing for the occasion should like a good idea.

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