Getting the right apparel for the Summer is easy- it’s all designed to keep you cool. There’s no guesswork about how warm or cool your gear needs to keep you- you always just want to be as cool as possible.
Things get complicated when the temperature drops. Dress too warmly, and you’ve made yourself into a hot and humid swamp on two wheels. Too cool, and you can just about feel your sweat freeze. To make things worse, it’s impossible to pick the exact right level of temperate-ness for any given ride, and one of two things happens. The first option is that your wardrobe for the day is a little too warm, and once you get warmed up you can’t stop sweating by the bucket. The other option is that you’re not quite insulated enough, and you never warm up- you just shiver for your entire ride and get sore joints at the end. To top it all off, what you need during your ride is constantly changing- warmer on descents and at the beginning until your muscles and heart get going; cooler on the climbs and once your blood is really pumping.
The trick to staying simultaneously warm, cool, and comfortable is on-the-fly versatility and the ability to regulate your temperature. It’s also super important to stay dry. Sweat is your body’s response to overheating, but it also freezes as soon as winter air hits it- a bad combo.
If I were starting from scratch, here’s the “complete package” that I would be looking to pick up:
Merino sleeveless base layer- either Smartwool or Sugoi- Merino wool is self regulating and may be the best wicking material out there.
Convertible Shell jacket- Gore Phantom Jkt- Detachable sleeves also work as pit zips for ventilation
Thermal Bib Knickers- Pearl Izumi Pro Thermal
Socks- Smartwool Cycling Lt PhD- Merino wool, compression through the arch promotes circulation, keeping your toes warm
Lightweight gloves- Pearl Izumi Cyclone or Gore Mistral
Toe covers- Pearl Izumi Cyclone or Gore Windstopper
Knee warmers- Pearl Izumi
Arm warmers- Pearl Izumi
Head band- Pearl Izumi
Long Sleeve merino base layer
Thermal bib tights- Sugoi RS Zero bib tights or Pearl PRO Softshell
Heavier gloves- Gore Alp-X
Shoe Covers- Pearl Izumi Barrier
Skull cap- Pearl Izumi Barrier
You can get a thermal jacket, but make sure it has pit zips or some other form of adjustable ventilation (the Tool jacket by Gore is awesome!). Another way to go is to add more variety to your mid layers, layer appropriately, and keep wearing the same shell as you do in cool weather.
Remember that you will never, ever be able to walk out the door with the perfect amount of warmth and never have to make adjustments. The idea is that you walk out the door with the ability to make adjustments and dial yourself in as you ride.