Most if not all of the things in the list are purpose-made for colder climates. During the warm months I am usually in shorts, a sleeveless shirt, slippers when I ride.
Outer Layer – Rothco Soft Shell Jacket
Starting with my outter-layer is this fine specimen of a jacket. It’s light, waterproof, wind resistant, and has a thin layer of fleece. Living in the Bay Area I am comfortable wearing this 80% of the year and then combine it with other layers for the really really cold commuting months of the year. This jacket has unzippable vents underneath the armpit area and on the back that allow air to flow in if I get too warm as well as a detachable hood.
The jacket also has an abundance of pockets that I find useful for things like keys, wallets, battery banks, etc. I don’t like riding with things in my pocket because they tend to fall out on long rides.
My favorite feature of this jacket is that the back vent is large enough to fit the charger for my Super73 which makes it convenient to carry if I know there will be a charge point on a group ride.
Middle Layer (1) – Akaso Heated Vest
This was more of a nice to have than a need to have, but I decided to give it a whirl. It’s definitely a luxury item to have in cold weather, but the key to defeating cold weather is layering. The vest itself is lightweight and doesn’t adds only a small amount bulk when combined with my jacket. It’s powered by an external battery that fits in one of the vest pockets and has a detachable hood. It’s another device to keep charged, but again I only use the heated feature for the VERY VERY cold months.
Middle Layer (2) – A Long Sleeve Shirt or Sweater
This is typically what I’ll be in after a ride. I’m lucky enough to work at a place that doesn’t require a suit and tie so I can get away with a sweater or some kind of button of shirt (long sleeve or otherwise). I find that after peeling off my jacket and vest this layer is typically what I’ll spend the day in while at work.
Inner Layer – Cotton T-Shirt or Athletic Material
At the core I always have a t-shirt that takes care of sweat. I’m good at sweating, so having an undershirt is always necessary for me. Brands like Under Armor use materials that wick away sweat from your body and then allow the sweat to dissipate so that you nor your shirt get too smelly.
Whether its hot or cold when I go out for a ride, I always have compression pants. Even on warm rides, compression pants help deal with sweat down below which make riding more comfortable. In cold weather these help retain heat in addition to managing sweat.
Staying with the theme of riding in colder weather, windproof and water-resistant pants are important. These keep your legs and nether regions warm, but not too warm. In the Bay Area cold morning usually means windchill and a bit of moisture. Before I put a lot of thought into my riding gear I would always ride in denim. I found that on a cold morning commute my pants would end up wet/damp by the time I got to work. The denim also didn’t do much in the way of keeping my legs warm. These pants are similar to jogger so they’re super-comfy to be in for long rides.
Gloves – FRDM Convertible Gloves
These are the gloves I use in from Fall all the way into early Spring. A lot of gloves you’ll find say they’ll work on smartphone screens, but all the ones I tried didn’t or didn’t work well enough to be useful. To solve for this I found convertible gloves to be the happy-medium. Whipping my thumb and index finger out of the gloves is super-easy and covering them back up is easy as well.