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30% OFF ENTIRE SITE

SHOP HOLIDAY

Our preppy inspired resort wear is comfortable, flattering, and made in the USA. Come sail with us!

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Dresses

SHOP
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Quilted Collection

Shop
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Sale

SHOP THE SALE

Let's play PICKLE!

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New
Quick Buy
Leah Top - Let's Play Pickle Pink/Blue $ 136.00 USD
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New
Quick Buy
Blair Long Sleeve Top - Let's Play Pickle Pink/Blue $ 150.00 USD
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New
Quick Buy
Swing Skort 13" - Let's Play Pickle Pink/Blue $ 154.00 USD
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New
Quick Buy
Country Club Skort with Ruffle, 17" - Let's Play Pickle Pink/Blue $ 154.00 USD
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Holiday Party Shop

Shop the Looks

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Quick Buy
Clare Top - Solid Black Ponte/Faux Cheetah Fur $ 150.00 USD
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Quick Buy
Kimmy Dress - Solid Red $ 180.00 USD
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Red Plaid Bow
Quick Buy
Molly Bow Back 3/4 Sleeve Dress - Black/Red Plaid Bow $ 194.00 USD
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Quick Buy
Molly Bow Back Dress - Black/Red Plaid Bow $ 180.00 USD
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We're the crew behind sailor-sailor

Female founders and best friends — we even have the same name!

About Us

Discover us on Instagram

sailor-sailor LOVE 🩷

We let our reviews speak for themselves!

4.98 average
213 reviews

Love it!

I love your clothes! Most of my closet is filled with sailor-sailor dresses and and tops. I am a sucker for bright colors and that’s what attracts me to your clothes!!

Margaret T
Love it!

Fits perfectly and it’s the prettiest top for Fall!

Mary D
Love it!

I own many Sailor Sailor dresses and this did not disappoint. Vacations, out to dinner or just shopping around town, sailor sailor is always my first choice!

Jennifer B
Love it!

Love the style, fabric and fit.

Jackie S
Love it!

This dress can be dressed up or casual, fits well, ordered up per other reviews. Customer service was excellent!

Jennifer F

Free Shipping

on all orders over $150

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Made in the USA

and designed by us in CT

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Sun Protective SPF 50+

to keep you cool