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Best Overall: Sperry Top-Sider Women’s Angelfish Loafer at Amazon "The shoe is guaranteed to win you fashion points, as well as keeping you safe on board."
Best Comfort: Helly Hansen Women’s Hydropower Sneaker at Amazon "Protects your feet from heavy deck fittings and rocky shores."
Best Style: Sebago Women’s Bala Slip-On Loafer at Amazon "Gets extra style points for being Kate Middleton’s sailing shoe of choice."
Best Budget: Sperry Top-Sider Women’s Sneaker at Amazon "One of the most affordable options on that still receives consistently good reviews for quality and style."
Best Quick-Dry: Adidas Women’s Boat Shoe at Amazon "Ideal choice for dinghy sailing, kayaking, canoeing and even walking through the shallows to your yacht tender."
Best Waterproof: Gill Short Cruising Boots at Amazon "Your feet will stay warm and dry throughout the day, greatly enhancing your enjoyment of being out on the water."
Best Practical: Rockport Women’s Sailing Club Work Shoe at Amazon "Looks cute while fulfilling a genuine safety function."
Best Casual: Aerosoles A2 Women’s Sailing Flip Flop at Amazon "A casual choice for those that spend most of their time in calm waters and don’t require anything more practical."
Our Top Picks
Best Overall: Sperry Top-Sider Women’s Angelfish Two-Eye Slip-on Loafer
The Sperry Top-Sider Women’s Angelfish Loafer receives excellent reviews for its ability to combine comfort, practicality and style. It’s a modern reinvention of the brand’s classic top-sider, with a lighter, sleeker shape and eye-catching panels of suede, nubuck and tumbled leather. Available in 13 colors (ranging from linen/oat to olive/taupe), this shoe is guaranteed to win you fashion points, as well as keeping you safe on board. The rubber sole features a solid grip that gives you traction on wet decks and slippery piers but is low-profile enough not to track mud onto your decks.
The shoes’ soft material is protected by a water-resistant finish, while the rust-proof eyelets are designed to withstand exposure to salt water and sea air. Adjust the two-eyelet lacing system to achieve the perfect fit. Decorative around-the-collar rawhide lacing and prominent stitching add to the timeless nautical aesthetic. Best of all, these moderately priced shoes feature a padded footbed to provide enduring comfort for long days spent out on the water.
Best Comfort: Helly Hansen Women’s Ahiga V3 Hydropower Sneaker
For unparalleled comfort, opt for the Helly Hansen Ahiga V3 Hydropower Sneaker. Featuring a sporty design, these low-cut, lightweight sneakers have a synthetic open-mesh upper. This material is both flexible and breathable (a real plus in hot weather). The shoes dry quickly, thereby reducing the likelihood of chafing after getting wet. The removable molded EVA midsole provides extra support, while structural overlays on the outside of the shoes protect your feet from heavy deck fittings and rocky shores.
The shoes also feature several elements designed for practicality and comfort. Antibacterial technology keeps your footwear smelling fresh even after repeated soakings; while reviewers particularly like the multi-directional grip system on the soles. The latter offers superior traction on deck, so you never have to worry about slipping or falling even in rough seas. Last but not least, the navy and magenta color scheme adds a touch of femininity to your sailing attire.
Best Style: Sebago Women’s Bala Slip-On Loafer
Fashionistas will love the Sebago Women’s Bala Slip-On Loafer, which gets extra style points for being Kate Middleton’s sailing shoe of choice. The British princess is often photographed in her taupe/white shoes; but with six colors to choose from (including navy/white and cognac/beige), you’re free to create your own unique trend. The hand-sewn moccasins pay homage to the classic docksider style, with decorative stitching, around-the-collar lacing and a delicate dual eyelet lace system.
They stand out from other docksiders for their slender shape and feminine colors, and for the contrast between the soft suede upper and the leather accents around the collar and eyelets. Whether you wear yours on the deck or to the marina bar after hours, you’re sure to turn heads. Practical elements include a traction-ready rubber sole and a three-quarter cushion sock lining with latex foam for added comfort.
Best Budget: Sperry Top-Sider Women’s Bahama Core Fashion Sneaker
The Sperry Top-Sider Women’s Bahama Core Fashion Sneaker is one of the most affordable options on that still receives consistently good reviews for quality and style. Made from cool, lightweight canvas, these hand-sewn moccasins are the epitome of casual fashion. The rust-proof eyelets are made to last (therefore adding to the value of your investment), while the uppers are securely bonded to the rubber sole.
The sole is non-marking, which means you don’t have to worry about leaving ugly tracks on your newly polished deck. In addition, the razor cut low-profile grip offers great traction on wet and dry surfaces; while the around-the-collar lacing ensures a secure fit. Most reviewers find that the integral arch support makes these shoes wonderfully comfortable. There are nine colors to choose from, including rose, white and blue.
Best Quick-Dry: Adidas Women’s Terrex Climacool Boat Shoe
If you plan on getting your feet wet, consider the Adidas Women’s Terrex Climacool Boat Shoe. With uppers made from Climacool perforated neoprene mesh, these shoes are super-breathable and exceptionally quick-drying. The soft-lined interior also features a built-in drainage system - making these the ideal choice for dinghy sailing, kayaking, canoeing and even walking through the shallows to your yacht tender.
The heel features a stretchable insert to allow for a perfect fit, while the synthetic sole boats Traxion™ grip for stability on a range of different surfaces. All of this practicality comes in a pretty package, defined by the shoes’ sleekly feminine silhouette and their on-trend color schemes.
Best Waterproof: Gill Short Cruising Boots
The Gill Short Cruising Boots are designed for men and women, and offer a more serious option perfect for coastal and inshore cruising. Designed to reach calf height, the boots are made from a 100 percent natural rubber compound and as such are completely waterproof (unless a wave comes in over the top, of course). Your feet will stay warm and dry throughout the day, greatly enhancing your enjoyment of being out on the water.
If you do get water inside, the quick-drying polyester lining ensures that you won’t be uncomfortable for long. Non-slip razor cut soles offer good traction on wet surfaces; while the removable cushioned inner sole protects your feet when you reach the shore. These boots are available in smart carbon or a more graceful silver.
Best Practical: Rockport Women’s Sailing Club Work Shoe
Specially designed for women that work on the water, the lace-up Rockport Women’s Sailing Club Work Shoe uniquely combines practicality and style. The attractive navy blue and tan leather upper conceals a steel-capped toe to help you avoid stubbed or broken digits. The rubber sole is slip-resistant; while the shoes themselves meet I/C75 electrical hazard, CSA impact and CSA electrical shock standards. Weary feet will welcome the soft feel of the brushed microfiber lining. The removable EVA cushion insert features a heel stabilizer cup to provide unrivaled support and comfort. Essentially, reviewers love that these shoes look cute while fulfilling a genuine safety function.
Best Casual: Aerosoles A2 Women’s Sailing Flip Flop
The Aerosoles A2 Women’s Sailing Flip Flop is a casual choice for those that spend most of their time in calm waters and don’t require anything more practical. The natural comfort of the flip-flop style is enhanced by the shoes’ double-padded memory foam insole. A diamond-patterned grip on the underside of the sole provides surprisingly good traction. Most importantly, the textured fabric strap achieves effortless summer style with a distressed look and an anchor pin embellishment. Choose your flip flops in one of four pretty colors, including pink, blue, black/gold and tan.