Sailing can be enjoyed year round so long as you dress accordingly. Of course what you wear in the summer will be the total opposite of what you wear in the winter time but by being prepared you can enjoy sailing no matter what the climate is throwing your way.

Basically there are two types of sailing that you can get prepared to do, warm weather and cold weather. They break down as follows:

WARM WEAHTER

Shirt: A lightweight short sleeved collared shirt is perfect for a hot day of sailing. Be sure that you go with a lighter color though as a darker color will absorb the sun and make you extra hot.
Shorts: A good loose fitting pair of shorts goes perfect in the summer time. Cargo shorts are nice as they allow for easy movement and the extra pockets are great for stowing extra gear and tools.
Shoes: Deck shoes are in order for a hot summer day. You can get what are known as ‘sailing shoes’ which are actually designed to grip a wet surface and will allow for easier movement on the boat.
Hat: A good hat will help keep the sun off your head and out of your eyes too. Again you will want to go with a lighter colored hat so that it doesn’t absorb the heat of the sun.
Sunglasses: A pair of sunglasses with good UV protection will ensure that your eyes are not over exposed to the harmful UV rays of the sun.
Personal Flotation Device: Also know as a PFD this is the most essential piece of clothing you can wear. This is what will keep you afloat should something happen and you need to bail out of your boat.
Sun block: Get a high SPF sun block to cover all the exposed skin you will have due to the lighter way you be dressing.

COLD WEATHER

Layers of shirts: Start with a t-shirt and then go with a turtle neck shirt and follow that with a heavy wool sweater or synthetic jacket. This three layer approach will keep you both warm and dry.
Foul Weather Gear: Also known as ‘float coats’ these resemble thick rain coats. They go on over your pants and there is also a jacket that can be worn as well. This will give you added protection from the cold weather and will also block any moisture from getting to you.
Sailing boots: These will slip right on and have your feet stay nice and dry the entire time you are sailing. To keep your feet extra warm you can wear a thick pair of wool socks.
Wool cap: This will keep your head nice and warm.
Sunglasses: Just like with warm weather a good pair with adequate UV protection will keep your eyes safe.
Personal Flotation Device: Yes you still need a PFD. A float coat is not a substitution for a PFD.
Sun block: You will still need some sun block for your face and neck area. Remember, any sunburn is a bad sunburn.

While some prefer sailing when it is warm and some prefer sailing while it is cold, they can both be equally as fun provided that you wear the right gear.