What to Wear Sailing

Sailing gear, gloves, clothes, shoes and more

Wondering what to wear sailing? Then you’ve come to the right place. I’ve worked hard to select sailing clothes that have proven to perform well time and time again. If you’re comfortable out on the water, then you’ll enjoy sailing so much more and you’ll get more sailing in, as cold weather won’t put you off. You can trust Gill Marine, Helly Hansen and Sperry.

You might also be interested in Cool Sailing Stuff.

Helly Hansen Boating sailing shoes - Men's Hydropower 4 Shoes Helly Hanson

Helly Hansen Men’s Hydropower 4 boating shoes

These sturdy boat shoes will give you great support and grip on deck with Helly Hansen’s ‘Ultra Storm Grip’ multi-directional grip system. Highly rated, with 4.5 stars average customer review.

Sperry Top Sider Bahama 2 Eye boating shoes Sperry Top-Sider men’s Bahama 2 eye deck shoes

Genuine hand-sewn construction. Canvas upper with rustproof eyelets. Non-marking Sperry rubber sole for the ultimate in wet/dry traction. A great value edition of the classic Sperry Top Sider deck shoes.

Helly Hansen Crew Sailing Cap - Helly HansonHelly Hansen Crew Sailing Cap

A good sailing cap is absolutely essential, to protect your head and face from the sun. Also available in white (recommended, to keep your head nice and cool)!

Chums Cap Retainer Cord with ClipsChums Cap Retainer Cord

How are you going to make sure you don’t loose that nice new sailing cap in the sea – this is how!

Gill Marine deck hand gloves - Championship short fingerGill Men’s Short Finger Championship Deckhand Gloves

You’re going to want to protect your hands from blisters caused by handling ropes. These great Gill Marine 4.6 star rated sailing gloves have a pre-shaped construction that fits your natural hand shape, plus stretch fabric on back for comfort.

Gill Inshore Lite Winter Sailing JacketGill Inshore Lite sailing jacket

Awesome 4.8 out of 5 stars customer rated Gill sailing jacket. Fully taped seams, adjustable cuffs and a rollaway hood all help to keep you warm and dry.

Helly Hansen Men's Crew Coastal Trousers - Helly HansonHelly Hansen Men’s Crew Coastal Trousers

4.8 out of 5 stars reviews for these excellent waterproof, windproof, breathable sailing trousers.

Gill Performance Padded Sailing ShortsGill performance padded sailing shorts

Hard wearing, quick drying Nylon tactel fabric with water-repellent finish. Reinforced seat panel that can accommodate optional pads if needed. 

Onyx PFD Personal Floatation Device for Keelboat useOnyx M-24 In-Sight Manual Inflatable PFD

If you’re going keelboat sailing, this is the thing to wear and be comfortable in all day. It comes with ‘ReliaPull Guide’ for predictable inflation. U.S. Coast Guard Approved.


PFD for sailing, SUPing, kayaking and canoeing by Stohlquist EdgePFD (Personal Flotation Device), by Stohlquist Edge

This PFD stretches with you for active sailing. Roomy front pocket for secure storage of snacks, chapstick etc. Ideal for wet sailing and SUP’ing. USCG approved. Also available in red and mango.

Gill Tactic Floating Sunglasses for sailing and boatingGill Tactic Floating Sunglasses

These Gill sunglasses are designed specifically to wear sailing, with UV protective and 100% glare free polarized lenses.

  • Hydrophobic outer coating sheds water and reduces salt residue for clear vision
  • Oleophobic technology on the inside face repels fingerprints, sun lotion and skin oils
  • Grade 1 Optic lenses designed to exceed EN safety standards
  • They look so good – you’ll want to wear them on land too!

Sports Sunglasses Holder Strap (4 Pack) - The Friendly Swede Sports Sunglass Holder Strap (4 Pack)

Also suitable for regular glasses/prescription glasses. Designed for thin frames – frames wider than 1 cm may not fit easily.