Shop Women’s Preppy & Nautical Resort Wear
For a life on the island, there’s nothing better than easy-going, yet polished and resort wear for women that works day or night. We love featuring styles that let you go from the beach to boardwalk and beyond. Whether you’re headed to the beach, tennis court, or out on a boat, or simply enjoying a day around town, we feature styles that are chic, refined, but always laid back.
Products List
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Vineyard Fleece Top - Oasis
Southwind Apparel$79.00Introducing our cozy and versatile Vineyard Fleece Top, the perfect companion for chilly days and cozy nights. This exceptional garment combines comfort, warmth, and style in one irresistible package, making it a must-have addition to your wardrobe... -
Vineyard Fleece Top - Patina
Southwind Apparel$79.00Introducing our cozy and versatile Vineyard Fleece Top, the perfect companion for chilly days and cozy nights. This exceptional garment combines comfort, warmth, and style in one irresistible package, making it a must-have addition to your wardrobe... -
Vineyard Fleece Top - Black
Southwind Apparel$79.00Introducing our cozy and versatile Vineyard Fleece Top, the perfect companion for chilly days and cozy nights. This exceptional garment combines comfort, warmth, and style in one irresistible package, making it a must-have addition to your wardrobe... -
Nantucket Fleece Tunic - Salmon
Southwind Apparel$98.00Southwind Apparel delivers on this Beach Fleece Tunic! The extra length looks great over leggings or skinny jeans. It's stand up collar gives it a beautiful, contemporary silhouette white the side pockets offer a practical flare! Best... -
Nantucket Fleece Tunic - Heather
Southwind Apparel$98.00Southwind Apparel delivers on this Beach Fleece Tunic! The extra length looks great over leggings or skinny jeans. It's stand up collar gives it a beautiful, contemporary silhouette white the side pockets offer a practical flare! Best... -
Stroll Oversized Wool Blend Crewneck Sweater - Exclusive at Island Pursuit
Pearls and Camo$159.00The Stroll Sweater Cozy up in style this season with unisex oversized wool blend merry sweater. The perfect mix of playful and polished, designed for a relaxed, effortlessly chic fit. The sweater features soft, wool blend yarns and classic crewneck... -
Flora Festiva Pima Knit Kimono Robe
The Cat’s Pajamas$125.00We searched the globe for the perfect knit fabric for our pajamas. We started with hand pulled Peruvian Pima cotton, which is known for its silky luster and soft texture. We combined this Pima cotton with Modal to get the perfect drape and added Spandex... -
Wynn Brushed Waffle Mock Neck Sweater
Michael Stars$118.00This is a fashion-first take on the traditional turtleneck. With a mock neckline, Wynn features dropped shoulders and long sleeves with ribbed cuffs. This easy-fitting top is warm, stylish and designed in our super Soft Brushed Waffle fabric. A... -
Salma V-Neck Brushed Waffle Top
Michael Stars$128.00Soft and stylish, Salma features a deep v-neckline, dropped shoulders and long sleeves with ribbed cuffs. With an easy fit and designed from our super soft brushed waffle fabric, this top is the perfect throw on and go piece for everyday... -
Cera Honeycomb Stitch Cardigan
Michael Stars$248.00Cera offers a fresh take on the ladylike cardigan. This structured style features a round neckline, front buttons and patch pockets. What makes it special is its rich, honeycomb texture and classic boxy fit. Ideal for dressing or with denim, this... -
Zola Ribbed Crew Neck Tee
Michael Stars$88.00A must-have, Zola is form fitting, with wide binding and a crewneck. Made from our soft Ultra Rib fabric that washes well and keeps its shape throughout wearing. Fabric: Ultra Rib: 48% Cotton / 48% Modal / 4% Spandex Care: Machine... -
Jones Wide Leg Pant
Michael Stars$138.00The classic wide leg pant, Jones has an elastic waistband for an easy fit. Made from our cozy Madison Brushed Jersey, the Jones is the elevated sweatpant that is a go-to for relaxing days in or running errands. Fabric: Madison Brushed...
