The SAILing Girls' Guide to Cute Boat Shoes

Women are constantly on a quest for the perfect shoe. And that extends to women sailors as well. SAIL editors MacDuff Perkins and Meredith Laitos went on the hunt to find that Jimmy Choo of topsiders, and here is what they came up with.
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Women are constantly on a quest for the perfect shoe. And that extends to women sailors as well. SAIL editors MacDuff Perkins and Meredith Laitos went on the hunt to find that Jimmy Choo of topsiders, and here is what they came up with.

In an attempt to find the Perfect Sailing Shoe, editors Meredith Laitos and MacDuff Perkins spent the fall sailing season testing dozens of women’s racing and cruising shoes. These were their favorites.


Slam Code One

Upon lacing up my SLAM Code Ones and stepping behind the helm of Synergy, a Beneteau First 40.7, I felt instantly stable and balanced, as if I were wearing lightweight, shiny hiking shoes. The increased support is a product of three generations of SLAM design that have produced a highly reliable, technical shoe. With four individually controlled sections in the contouring heel, one part of your foot is always flat on the deck, creating long-lasting comfort in dynamic conditions. This control also reduces stress on the ankle and allows for better posture when heeled. The synthetic upper and water-repellant insole shed water quickly, a feature your gear bag will thank you for. $89.95 (unisex);


Vibram FiveFingers

Runners praise Vibram FiveFinger shoes for helping correct their gait and posture, and now sailors are beginning to embrace them as well. It’s not hard to see why. With abrasion-resistant, razor-siped soles and quick-drying mesh bodies, they proved to be both stable and comfortable during a long day on a J/24 foredeck. We wore these in place of our typical hot-day clunky water shoes and even the most cynical old salt told us, “Hey, your feet look super cute!” We were as surprised as anybody. $85;


Adidas Boat Lace

For a company just getting its toes wet in the sailing shoe arena, Adidas hit the nail on the head. The Boat Lace shoe is constructed with CLIMACOOL technology, which merges quick-drying mesh uppers with insole drainage for a cool and comfy fit. The protective toecaps and grippy soles provide additional safety, and the lightweight end result (only 7oz a pair) is a breeze to cart around. Best of all, Boat Lace shoes are extremely customizable, allowing you to add personal or team touches to every pair. At, buyers can choose between open-water or closed-street outsoles, regular or speed lacing and 22 combinable colors. They even come in different scents. $85 (unisex);


Chatham Women’s Crest G2

European shoes have undeniable appeal, so when Chatham sent us a pair of their velvety smooth, bright red Crest G2s, we immediately ditched our workplace stilettos for the buttery leather comfort the British shoemaker is known for. You might try to reason that you don’t need another pair of boat shoes rolling around your closet, but trust us, you need these. Why? Because it feels so fabulous to say: “Oh these? They’re just my European deck shoes. No biggie.” $110;


Sperry Authentic Original Boat Shoe

It’s hard to say when the trend resumed, but retro Top-Siders (and their Wayfarer brethren) are back in style for sailors and non-sailors alike. Sperry recognized the trend and ran with it, producing several modern takes on the classic boat shoe, including ones with animal prints, heels, madras patches and—our favorite—metallic shines. These shoes embrace the tried-and-true tradition of solid Sperry construction (genuine hand-sewn material, rust-proof eyelets, non-marking soles) but add just enough pizzazz to make a statement wherever you wear them. Strolling around the Annapolis boat show this October, these kicks got more than a few nods. $125;


Sebago Bala

Sebago Castines have been popular around the SAIL office for years, thanks to their incredible support and comfort. So when the Duchess of Cambridge, Kate Middleton, stepped out in Canada wearing the Sebago Bala, we just about died. Getting our own pair turned us into raging sailor princesses, renaming our boat the HMS SeaDeucer and serving tea on the rail. The ultra-feminine construction practically screams “wear me with capris and a tiara!” And while club members burst into fits of laughter when we walked into the bar wearing a peacock fascinator on our heads, the Balas produced the right kind of inquiries, such as, “Where on earth did you find such cute boat shoes?” Peasants are so precious when they think they can address us without curtsying first. $95;


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