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Warm Weather & Water
If you live in a hot part of the world that has warm water, dressing for kayaking is simple. Your biggest challenge will be staying cool, hydrated, and protected from the sun, and this should be something that you're used to doing. The most simple solution involves using sunscreen and wearing a hat. Sunglasses are also helpful because the glare off the water can be blinding, and you'll want to use some type of retainer strap so you don't lose them. Of course the best way to protect yourself from the sun is to cover up, so you might want to wear a light long-sleeved shirt. Below the waist, surf shorts and water shoes or sandal like Tevas work great.
Warm Weather & Cold Water
Dressing for cold water is far more difficult, especially when the air is warm. Even on the hottest days, if you find yourself swimming, the cold water can suck the heat out of your body at a surprising speed. If you're paddling a sit-on-top kayak, you have to expect that you're lower body is going to be wet, whereas a sit inside kayak will protect you a lot more from both the wind and the water. On the other hand, if you flip when paddling a sit-on-top kayak, you can just climb back on the boat. But if you flip a sit-inside, it will take you a lot longer to get back on board, which means you'll spend more time in the cold water.
Close to Shore vs. Off Shore
Of course the best strategy is to avoid capsizing altogether, and this is easy to do in a rec kayak, as long as you stay in areas that are protected from heavy wind and waves. On the other hand, if you're going to paddle a narrow sea kayak in cold water, you should take professional instruction and learn the different capsize recovery techniques.
Whatever boat you're paddling, it only makes sense that you stay close to shore, so that if you do flip, you have the option of just swimming to shore, while your buddies gather your equipment.
If you're going to be paddling in more committing areas, where you won't be able to get to shore very often, it's important to choose the right clothing. You want to be able to wear something that will keep you warm if you get wet, but that you won't overheat in when you're paddling. A neoprene Farmer John wet suit works well for this purpose, because it insulates when it's wet, and doesn't get in the way while you're paddling.
Cold Air & Cold Water
When both the water and air temperature are cold, you have to be aware of the threat of hypothermia and understand that paddling in these types of conditions isn't for everyone. But if you are going to hit the water, you need to use clothing that will keep you warm, even when they are wet.
Synthetic fabric like fleece, neoprene, and polypropylene are good for this reason, and it's best to use a couple of thinner layers instead of one thick layer. Wool also works well although it's slow to dry and heavy when it's wet. Cotton is one of the all-time worst materials to wear when it's cold. Cotton actually draws heat from your body when it's wet.
• Paddling Tops/Bottoms
Over top, you'll want to have an outer shell that keeps the wind off your body. A waterproof nylon jacket and pants will do the trick, but at you local outdoor or paddling shop, you'll find paddling tops and paddling bottoms that are designed specifically for the purpose. On you feet, neoprene booties and socks will help keep your toes warm.
• Dry Suits
The ultimate protection against the cold, though, is the dry suit. A dry suit uses latex gaskets at the ankle, wrists, and at the neck, which keeps all the water out. Dry suits are expensive, but if you spend a lot of time paddling in cold conditions, they are well worth the price.
• Spray Skirts
If you're using a sit-inside kayak you can also use a spray skirt, which keeps the cold water out and keeps the hot air in. When you're putting on a spray skirt, you want to start along the back and work your way up along the coaming, then pull the skirt over the front coaming, making sure you leave the rip cord out, because that's what you're going to pull to pop the spray skirt if you do end up flipping.
This video provides an introduction to the different weather and water situations to consider when dressing for kayaking.