Let’s start from the top down and assume that it’s 8C and raining off and on. EPIC spring classic conditions.
Wear a cap under your helmet. It doesn’t need to be fancy. Just a regular $20 cap will do the trick. It will keep your head warm and will let the rain drop off the brim of the cap instead of into your face. It also gives your eyes something to hide behind when water is being sprayed into your face from the wheel in front.
Merino base layer. How I wish I discovered the magic of merino many years ago. This stuff is absolutely brilliant. It will keep your core warm and dry by wicking the sweat away from it. For the Warny I wore a Rapha short-sleeved merino base layer which was the first step in being comfortable for 8hrs on the bike. Icebreaker also specialises in making excellent merino products. I can’t recommend merino wool base layers highly enough.
Arm Warmers. I prefer to use arm warmers rather than a long sleeve jersey so that I have the option of taking them off if I get too warm. They also have a tighter fit which I find holds the warmth in better – even if wet.
Vest. A good vest is just as important as a good base layer. It’s an excellent choice to bring in questionable weather conditions because you can unzip it if you get too hot, or take it off all together. It’s such a compact piece of clothing and unless is very hot out I’ll almost always bring a vest with me.
Rain jacket. Personally I find that almost any rain jacket is too muggy and warm when racing (again, training is a different story – you need a rain jacket when training). What I like to use is a rain vest. It will keep your torso relatively dry but won’t make you sweat. There’s nothing worse than overheating in a plastic bag.
Gloves. A good set of water and wind resistant gloves is extremely important. Having proper grips on the gloves is just as important so you can hold the bars properly and change gears. I once had a set of Nike winter gloves that were terrific. I wish I could find them again. They had these great sticky grips on the palm and on the fingers so I had no problem gripping the handlebars, brakes and shifters.
Knicks. I can’t get myself to spend $100 on a set of jeans, but I can see the value in a $300 set of knicks. For the Warny I wore two sets of knicks. I used my team knicks on the outside along with my top-of-the-line Assos knicks on the inside. Two sets of knicks aren’t necessarily required, but I wanted that Assos chamois to be on my backside so I could walk the next day. I know many guys who will replace their team issue chamois with Assos chamois.
Chamois Cream. I don’t bother with chamois cream every time I ride, but it’s a absolute must when riding long distances, especially in the rain. It’ll keep you from getting saddle soars and chaffing. You can buy some name brand chamois cream which is good, but a cheaper option that does the trick is Bepanthen nappy rash creme.
Shoe Covers. A set of thin neoprene shoe covers won’t keep your feet dry, but will keep them warm from the wind. There’s nothing worse that having numb feet.
Socks. DeFeet and Capo make the best socks in my opinion. A set of medium thickness merino socks are great to keep your comfortable in cold weather.
Embrocation. Belgian knee warmers as it’s called. It provides warmth for the legs and keeps the blood circulating and the muscles as supple as possible. It doesn’t actually keep you warm – it just redirects blood flow to the areas where it is applied. When it’s really cold, put a thick coat of Vaseline over your legs as well. It’s a bloody mess, but will hold the heat in and repel the water.
Leg and Knee Warmers. Some people like to use these, but I find them too warm when racing. Unless it’s really cold out, you’ll see most of the pros wearing nothing on their legs as well. I’ll use knee warmers once in a while at races, but only when it’s dry and cold out. If they get saturated with water they’ll start to sag and become uncomfortable.
The key to dressing comfortably is by taking care of your core and your extremities. If it’s raining out, you’re not going to stay dry. There’s no use fighting it. The trick is to hold your body heat in while not overheating. I find that when I’m standing at the start line I’ll be freezing cold. This is okay because it’ll only take 10 minutes to warm up. It takes a bit of experimenting to figure out how your own body needs to dress, but once you do you can focus on the ride or race instead of how uncomfortable you are.