Sailing Footwear Buying Guide & Comparison

Crosshaven sailing boots worn on a wet deck

Choose sailing footwear for the conditionsCompare waterproof boots, quick-drying technical shoes and smarter deck footwear for warm days, wet decks and colder offshore use.

Sailing footwear needs to balance wet-deck grip, drainage, comfort and weather protection. A traditional deck shoe works well for fair-weather sailing and shore use, while technical trainers dry faster during active sailing. Waterproof boots offer greater protection in spray and cold conditions; insulated gaiter boots are intended for the most exposed days.

This guide compares the main choices stocked by A Farley. For classic leather boat shoes, use the separate deck shoes buying guide.

QUICK ANSWERChoose a lightweight technical shoe for warm, active sailing; a waterproof sailing boot for repeated spray and cooler weather; an insulated gaiter boot for colder offshore conditions; or a GORE-TEX deck shoe when you want waterproof protection in a smarter low-cut style.

Choose sailing footwear by use

$Dubarry Ultima waterproof sailing boot$ Waterproof sailing boots $Dubarry Crosshaven insulated gaiter sailing boot$ Cold & offshore conditions

Technical sailing shoes $Dubarry Mariner waterproof leather deck shoe$ Deck shoes & shore use

Sailing footwear compared

Model	Best for	Weather protection	Fit & construction	Grip / drying	Shop
$Dubarry Crosshaven sailing boot$ Dubarry Crosshaven	Cold, exposed and offshore sailing	Waterproof 350g Duratherm insulated membrane; water-repellent gaiter	ExtraFit gaiter boot; drawcord collar, reinforced toe and heel, drainage mesh	NonSlip-NonMarking outsole; D-Chassis support and reflective detailing	Shop Crosshaven
$Dubarry Ultima sailing boot$ Dubarry Ultima	Classic all-leather waterproof sailing protection	Waterproof, breathable membrane and water-resistant crushed leather	Standard fit with an expandable Lycra calf section	Direct-moulded PU/rubber NonSlip-NonMarking outsole	Shop Ultima
$Dubarry Ultima ExtraFit sailing boot$ Dubarry Ultima ExtraFit	Wider feet, higher insteps or fuller calves	Waterproof, breathable lining with all-leather upper	ExtraFit last gives more room through foot entry, instep and calf	Non-slip, non-marking sailing outsole	Shop ExtraFit
Dubarry Hobart	Lightweight waterproof protection without a leather boot	Waterproof and breathable construction	Lightweight pull-on design; standard and ExtraFit versions available	Quick-drying materials with a deck-focused outsole	Shop Hobart
$Dubarry Mariner waterproof deck shoe$ Dubarry Mariner	A smarter waterproof shoe for deck and shore	Waterproof, breathable lining with water-resistant leather	Classic leather moccasin shape with secure lacing	Non-marking sailing outsole; more structured than a mesh technical shoe	Shop Mariner
Dubarry Mauritius	Warm-weather and highly active sailing	Not a waterproof boot; designed to drain and dry quickly after spray	Unisex mesh/Lycra upper with bungee-and-toggle adjustment	Water-dispersion channels, D-Chassis heel support and non-marking sole	Shop Mauritius
Dubarry Sydney	Lightweight everyday performance on deck	Breathable, quick-drying upper rather than a waterproof membrane	Secure lace fastening; broad UK size range	Flexible non-marking outsole for wet and dry surfaces	Shop Sydney

How this list was chosen: the comparison uses current A Farley product specifications, availability and net sales from 7 May to 3 November 2026. Technical sailing footwear sells in lower volumes than classic deck shoes, so products are ordered by intended use rather than presenting sales rank as a quality judgement. Specifications can change; check the individual product page before ordering.

Sailing shoe or sailing boot?

Choose a technical shoe when

You are sailing in warmer weather, moving actively and expect footwear to get wet. Quick drainage, low weight, secure lacing and a non-marking sole matter more than insulation. These shoes are not a substitute for waterproof boots in cold spray.

Choose a sailing boot when

You need protection from repeated spray, cooler temperatures or prolonged exposure. Leather membrane boots balance waterproofing with smarter styling; lightweight synthetic boots prioritise lower weight and faster drying. A gaiter boot adds the greatest foul-weather protection.

Standard fit or ExtraFit?

ExtraFit is intended to give more room through the foot entry, instep and calf. It is useful when a standard tall boot feels restrictive or when thicker technical socks and foul-weather layers are worn. It should not be bought automatically: a boot that is unnecessarily loose can reduce stability. Measure the widest part of the calf while wearing the clothing you use on the water.

Waterproof, water-resistant or quick-drying?

A waterproof membrane is designed to keep external water out while allowing moisture vapour to escape. Water-resistant leather can tolerate spray but is not the same as a sealed waterproof construction. Quick-drying mesh deliberately prioritises drainage and ventilation; water may enter, but the shoe recovers more quickly. Choose according to conditions rather than treating one approach as universally better.

Wet-deck grip and non-marking soles

Look for a rubber outsole developed for wet surfaces, water-dispersion channels or siping, and a secure fit that limits movement inside the shoe. “Non-marking” means the compound is designed not to leave dark scuffs on deck surfaces; it does not make any outsole slip-proof. Salt, oil, algae and worn tread can all reduce traction, so rinse soles and inspect them regularly.

Looking after sailing footwear

Rinse off salt and grit with fresh water after use, remove insoles where appropriate and dry footwear naturally in moving air. Do not place leather or membrane footwear directly on a radiator. Clean and condition leather with products suited to its finish, and check that drainage channels are clear before the next trip. Browse footwear care products for suitable cleaners, protectors and conditioners.

Frequently asked questions

Are sailing trainers waterproof?

Usually not. Technical sailing trainers often use breathable, quick-drying materials so water can drain and the shoe can recover quickly. Check the exact model specification rather than assuming a low-cut sailing shoe is waterproof.

Can deck shoes be used for sailing?

Yes, provided the model has a secure fit and a suitable non-marking outsole. Traditional leather deck shoes work especially well for fair-weather sailing and shore use. For active sailing or repeated spray, a technical shoe or waterproof boot may be more suitable.

Which sailing boot is warmest?

The Crosshaven is the most cold-focused option in this comparison because it combines a tall gaiter with a 350g insulated membrane and thermally lined insole.

What is the difference between Ultima and Ultima ExtraFit?

Both are waterproof leather sailing boots. ExtraFit gives more room through the foot entry, instep and calf; the standard Ultima is the better starting point if you do not need additional volume.

Should sailing footwear fit tightly?

It should hold the heel and instep securely without crushing the toes or restricting circulation. Allow space for the socks you will actually wear, but avoid excessive movement that could cause rubbing or reduce stability.

How should wet sailing footwear be dried?

Rinse away salt, loosen fastenings, remove insoles where appropriate and dry naturally in a ventilated place. Avoid direct heat, which can damage leather, membranes and adhesives.