I moved here from Florida. Coming from beaches, shorts and lots of sunlight, it's difficult to understand winter before getting here. Anyone who tried to convince me to buy "warm winter clothing" to prepare just sounded unreasonable. Now that I'm here, I'm freezing! I'm trying to understand layering and how to stay warm, but I worry that I'll become a hermit, bound to my apartment and never able to step foot outside my door unless pulled. I know that's not necessarily how winter should go and there are ways to enjoy it and adjust, I just don't know how. Help!
Freezing in Philly
The fact that you know to use the word "layering" puts you way ahead of many warm-weather transplants, so I wouldn't call you completely clueless. Then again, layering isn't everything. Case in point: Several years ago, I met an Israeli who was in Philly doing a post-doc. He asked me in November if he'd need a winter coat. I said yes. Then he said that his plan was to wear all his sweaters at once when he left the house in the winter months, and would a coat really be better than that? I still said yes. I literally never saw the guy again, but I think about him all the time when the weather gets cold. (Then I inevitably think of the Friends episode where Joey wore all of Chandler's clothes at once. But I digress.)
You need a warm coat, it's true. You also need a hat, gloves or mittens, a scarf and warm socks. I can't say enough good things about Smartwool brand socks. You don't necessarily need winter boots, per se, but since boots seem to be most women's footwear of choice anyway, get a pair that is warm and waterproof with some kind of traction on the bottom for icy days. (That means something with more substantial insides than rain boots and more substantial outsides than Uggs.) You can get gloves that are smartphone compatible. You can get a scarf that's also a fashion statement. Those things are great, but you also need things that are actually warm and that won't devastate you if they get lost — particularly when it comes to gloves.
One of the things I find hardest about getting dressed in winter or summer is the difference between indoor and outdoor temperatures. In the summer, I want to wear short sleeves and not freeze in air-conditioned buildings. In the winter, I'm happy cuddling up in my thick sweaters so I prefer not to go into places with the heat blasting so high that it feels like a sauna. Since you don't get to control the temperature everywhere you go, you've got the right instinct about layering. Cardigans are great because you can easily take them on and off depending on the indoor climate, but any sweater with a lighter weight shirt underneath is also a good way to go. Two pairs of thin socks can sometimes protect your feet from the cold even more than one pair of thick socks. Tights or leggings underneath jeans is another trick for warmth.
As for controlling the temperature, you do get some control at your home (depending on your apartment arrangement, I guess), so shoot for 68-70 degrees when you're in and 64-65 when you're not. That way, it's liveable, but you're (hopefully!) not spending all your money on utility bills. Keep a pair of slippers by the door and a couple of blankets on the couch and you'll be fine. Slippers are also useful to avoid tracking ice and salt through your house.
You have to do more planning in the winter to go out safely and comfortably, but do make an effort to make plans. You can always invite people over to your place and use your winter inexperience as an excuse. Cabs in Philly are plentiful, so you can splurge on them if the mere idea of walking in the cold makes you shiver. For sure, Philly is a shock from what you're used to, but I'll end with this to give you some perspective: When we had 2-4 inches of snow in Philly a couple of weeks ago, it was snowing 2-4 inches an hour for two days straight in my hometown of Fredonia, NY. So, as Jews the world over like to remind each other, it could always be worse.
Stay warm, and be well,