I moved from Hawaii to Washington state. Here, it’s 46º. Back home, it’s 81º. So you can see the difference in temperature I’ve had to adjust to.
So far, it’s been easy. I have long sleeves tops on all the time, which is no big deal, as I liked and often wore (light fabric) longsleeved shirts back home.
It started getting cold in November, at which point I couldn’t lounge around in a shirt and shorts anymore. At present I’m wearing a t-shirt, hooded cotton jacket, and thick sweatpants. I’m not what I’d call warm, but I’m not uncomfortably cold. Occasionally, I’ll put on a pair of socks if my feet get cold, but I don’t really need them.
Going out after sunset is fun. A coat or jacket is absolutely necessary, as are long pants. I really wish I had flannel-lined pants, of any kind. Jeans alone don’t cut it. I have silk underwear, which helps a little, but I could be warmer when I wear them. I also have gloves, as my hands tend to get cold easily.
Recently I got some all-weather boots from Land’s End, and I love 'em. My feet stay warm and dry, and I don’t worry about slipping on the wet ground as much. (I’m a klutz, so I worry about it to some degree all the time.) I recommend getting similar footwear.
It’s not that much colder at night than it is during the day, so I’m pretty comfortable wearing light sweatpants and a t-shirt to bed. [TMI] Heck, sometimes I pass up on clothing altogether and am happy under my thick comforter. [/TMI]
I understand it’s supposed to get colder in January. We’ll live. We’re not using the heater now, so even if it does drop another 10-20 degrees, we can crank it up and be comfy.
I think you can learn to enjoy the cooler temperature, but it’s not something you can force yourself to do. I came here wanting colder weather, and I got it. Still, sometimes I curse Mother Nature for causing my fingers to go numb.