The Keys are known for laid-back sports such as scuba diving and snorkeling, but in the past years other sports like kiteboarding, paddle boarding and kayaking have gained popularity. The owners of Otherside Boardsports, who are both kiteboard instructors, recognized the trend in 2007 and opened a core boardsports retail shop in the heart of Islamorada. They carry a variety of swimwear with a focus on sturdy styles that won't malfunction while out on the water. Men can find boardshorts from brands like O'Neill, Volcom, Rusty, Jetpilot and Dunkelvolk. Women will find a variety of suits from O'Neill, Volcom, Mandee Pants, Stone Wear and Rusty. They're the only shop in the Keys that carries Montce Swim--a small boutique brand that does mostly custom suits.
Recommended for Swimwear Shops because: A core boardsports shop, Otherside carries performance wear for athletes and active people who can't afford wardrobe malfunctions on the water.
Claudia's expert tip: New to boardsports? Sign up for lessons and tours.
World Wide Sportsman is a two-story nirvana for fishermen that offers one of the largest selections of saltwater, freshwater and fly fishing gear you'll ever find in one place. Men, women and children will find a wide variety of outdoor apparel and accessories in name brands like Timberlake, Columbia, Costa Del Mar and Guy Harvey. On the second floor, they have a full selection of swimwear including separates and one-pieces for women and boardshorts for men. They also carry coverups to match. Even if you're not shopping, the store is worth a visit for the saltwater aquarium filled with indigenous fish and full-size boat parked in the middle of the building. You can actually climb aboard the boat, which is the sister ship to Ernest Hemingway's beloved Pilar. Next door is the popular Islamorada Fish Company, or you can head upstairs to the Zane Grey Lounge.
Recommended for Swimwear Shops because: Head upstairs to find active on-the-water suits. Women can choose from separates and one-pieces, while men will find boardshorts and swim trunks.
Claudia's expert tip: Look for apparel and accessories with the store's own label, which are usually less expensive than name brands.
Finding a bathing suit that fits can be a challenge no matter what your size, but Lion's Lair Swimwear and Lingerie has come up with a winning solution. This little-boutique-that-could is filled with styles for all shapes, including mix-and-match separates in DD cup and up, as well as plus sizes. The knowledgeable staff is hands-on, helping you find that perfect fit in the dressing room. Owner, Kim Berger, prides herself on hand-selecting high-quality brands that appeal to a wide range of women--old and young--such as Sunsets, Swim Systems, Tara Grinna, Eco Swim, Freya, Fantasie, and Elomi. So many fans look forward to coming back each year on vacay, that Lion's Lair has earned a brisk mail-order business. After seeing the challenges of her large cup size customers, Berger added on lingerie and doubled the size of the store. You'll also find a wide selection of cover-ups, accessories and gifts.
Recommended for Swimwear Shops because: Filled with swimwear styles for all shapes, this boutique carries mix-and-match separates in DD cup and up, as well as plus sizes.
Claudia's expert tip: Take advantage of the knowledgeable sales staff, who can measure you for the perfect fit.
No beach wardrobe would be complete without a classic shift dress from the mother of resort wear--Lilly Pulitzer. Pair it with a matching bikini in one of their signature styles, and you'll be ready to hit the beach. Their mix-and-match separates make it easy to create the perfect suit. Just like the rest of the boutique, they come in a dazzling array of colors--bright pinks, greens and aqua blues--and whimsical tropical prints that set the Pulitzer-style apart. You'll also find timeless dresses, skirts, tops, pants, shorts, sweaters and all the accessories in identical prints. Their Resort Collection alone is filled with hidden flamingos, giant hibiscus and sun soaked bougainvillea. Slip into a comfy shift dress and channel your inner Jackie O., who made Pulitzer a household name.
Recommended for Swimwear Shops because: Separates make it easy to find the perfect fit, and you can mix up the dazzling prints and patterns to personalize your look.
Claudia's expert tip: No beach wardrobe would be complete without a classic shift dress.
No matter what your water sport--even if it's just sunbathing--Ron Jon Surf Shop has what you need packed in their blue, two-story Conch House style building. Steps away from Mallory Square, their 4,400 square feet store has swimwear and accessories for men and women of all ages. They carry their own signature line, as well as name brands like Hurley, Billabong, Volcom, Roxy and more. Their laid-back but helpful staff is available to help you find the right fit. Post-swim, they've got you covered, literally, with board shorts, tees, tanks and flirty dresses.
Recommended for Swimwear Shops because: Steps away from Mallory Square and the cruise ship port, Ron Jon Surf Shop offers swimwear and accessories for men and women of all ages.
Claudia's expert tip: Check out their selection of wearable and gear-mountable GoPro Cameras--a hands-free way to capture your vacation.
Ocean Key Boutique is not your normal hotel gift shop. This stunning boutique is designed to quickly outfit men, women and children in the perfect vacation wardrobe from head to toe. In fact, shoppers often leave the store wearing their new purchases. One of their main clothing lines is Island Company, which labels itself an "escapist brand" with resort wear, cute bikinis, classic swimwear, linen separates, vintage sunglasses and island accessories. The boutique also stocks Tommy Bahama for men and women--the classic go-to for any tropical wardrobe. For women, the bathing suit section is rounded out with mix-and-match separates by Maaji swimwear. This youthful brand combines an unexpected mixture of prints, textures and cutting-edge silhouettes. They'll also find colorful coverups to match. Men can choose swim trunks and boardshorts from Quicksilver, Tommy Bahama, Island Company and Reyn Spooner.
Recommended for Swimwear Shops because: A well-rounded swimwear selection for men and women with Tommy Bahama, Island Company and Maaji prove this is not your typical hotel gift shop.
Claudia's expert tip: Ocean Key Boutique also carries coastal and whimsical gifts, as well as signature items from Spa Terre.
The modern, industrial decor, reminiscent of a New York boutique, is your first clue that Evolution is not the usual Keys-ey shop. This two-story boutique is packed with men and women's clothing by designers you won't find anywhere else in Key West--or in your regular mall for that matter. They carry brands designed and made in the U.S. like LASC, Pistol Pete, Andrew Christian and Adriano Goldschmied, as well as British and Dutch clothing lines GStar, Bench and Superdry. Men will be pleased to find a wide selection of swimwear from Speedo-style to board shorts. Women will be drawn to the flowy dresses by good hYOUman and accessories like colorful Herschel bags and rose-colored sunglasses from Minnie Rose.
Recommended for Swimwear Shops because: Men will find swimwear from Speedo-style to board shorts by unique designers like Andrew Christian, 2xist and GStar.
Claudia's expert tip: While they carry women's clothing on the second floor, they only carry swimwear for men.
Shop to the sound of the thumping house music at this men's clothing store on Duval Street. A hipster's paradise, the boutique is packed with casual wear and accessories by modern brands like Ben Sherman, Buffalo David Bitton, French Connection, J. Fold and Dosh. They have a wide selection of swimwear, beach towels and water-related gear from Diesel, RVCA, Aussiebum, Anarchy sunglasses and Peter Grimm headwear. Graffitti has been a go-to spot for men's fashions in Key West for over 25 years, and they moved to their current location at 721 Duval Street in 2011. In the beginning, the store catered primarily to gay men, but the inventory has been updated since the move to appeal to all young, urban-oriented men. Specializing in items that you can't find at larger stores, Graffitti has the only Lucky jeans south of Miami and an exclusive contract with PanAm.
Recommended for Swimwear Shops because: This hipster's paradise is packed with swimwear and accessories by modern brands like Diesel, RVCA, Aussiebum, Anarchy sunglasses and Peter Grimm headwear.
Claudia's expert tip: Once targeting primarily the gay male market, Graffitti has updated their inventory to appeal to all young, urban oriented-men.
Women of all ages will be pleased with the collection of swimwear at Paradise Vision. They carry a wide array of mix-and-match separates including triangles, halters, bandeaus and underwire tops paired with American and Brazilian cut bottoms for a selection of contemporary body-flattering silhouettes. Fun youthful bikinis feature embellishments like crochet, beading, braiding and fringe by designers like Guria Beachwear, Luli Fama Miami and Lucky. For those looking for more coverage, swimwear lines like Christina, Captiva and Penbrooke Swimwear offer tankinis, swim skirts and one-pieces in regular and plus sizes.
Recommended for Swimwear Shops because: This boutique covers all the bases from youthful bikinis to classic tankinis by well-loved brands like Luli Fama Miami and Christina.
Claudia's expert tip: Don't miss their fun accessories like hand-dyed sarongs with matching headbands by Batik Bali.
Aqua Beachwear is part of a small boutique chain for that includes over a dozen stores throughout the Florida, Arizona and the U.S. Virgin Islands. If you usually dread swimsuit shopping, their helpful staff can help you find the perfect suit no matter your shape and size. They know their inventory and the styles that work for different body types. The suits come in a variety of different cuts, from one-pieces, monokinis and bikini separates in a myriad of colors and prints. Brands range from affordable to top designers like Gottex, Juicy Couture, DKNY, Ralph Lauren, Betsey Johnson, Miraclesuit and more. Add a matching coverup for a flattering ensemble you'll love. They also carry a selection of boardshorts for men.
Recommended for Swimwear Shops because: Top-notch customer service, flattering styles and a wide selection of designer brands for women sets Aqua Beachwear apart.
Claudia's expert tip: Aqua was formerly known as the The Beach House, so don't be confused by the name change.