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Once it hits about fifteen degrees things get pretty miserable. Not to derail the convo either, but I will say, investing in a proper set of baselayers and a windproof jacket will really help out whenever it's super cold outside. Most people who wear cotton--t-shirt, hoodie, longsleeve, whatever--next to their skin put themselves in a pretty crappy position as soon as they begin to sweat because that material soaks up moisture and keeps it close to your skin, which, in turn, makes you pretty damn cold. Add in a top layer that allows wind to penetrate, and you're basically screwed 'cause that cold air is going to push right through to your core, cool down that layer of sweat even more, and your body is pretty much robbed of any insulation it may have worked to create.
If yall have tips on making skating under 40 degrees less of a struggle, derail away...
It's really all about moisture management because moisture and cold air don't mix well. Think about whenever you're in a hot shower and you're fine because there's fresh warm water running continually, but as soon as you step out and are exposed to cooler air with a a bit of water on your body, you're much colder. Also, certain fibers are a lot more effective at pulling moisture away from your body and onto the face of the fabric so that you remain dry and work to keep itself warm while your sweat is pushed forward and allowed to dry quickly off of the face of the fabric. Like I said, cotton is pretty crappy for managing moisture because it just retains your sweat and continually soaks it up and doesn't dry quickly at all. Merino wool and polyester are probably your best bet, with merino being better but more expensive. I use Patagonia's thermal weight baselayer because they're very lightweight and don't add unnecessary bulk to restrict your mobility when skating; they also have a ribbed fleece interior that pulls your sweat forward while the non-ribbed part adds some breathability. I guess the next step is something that can insulate. If it's not super cold, like ten to upper teens, a hoody and a sweatshirt or something like that will work just fine in combination with a windbreaker, and while it may be made from cotton, it's not as large a concern since it's not right at your body--still, however, it's best to avoid cotton whenever you can. If you're really dedicated and it's colder than that, I'd use a jacket with either down or synthetic insulation. Like the wool, down will be lighter but a bit more costly. Then last is a windbreaker so that cold air/wind doesn't penetrate all of the insulation your body has worked to create. Another key thing is to avoid cotton socks if you can. Socks are another time where merino wool prevails because you won't be faced with moisture being near your feet and having to worry about it cooling you down. My response is probably a bit lengthy and nerdy, but I spend a lot of time outside during the winter off of my skateboard and a lot of the same techniques cross over really well to cruising around on shitty days.