1. Amass a collection of cashmere sweaters/sweaterdresses in various colors and cuts. They’re not that expensive if you buy them vintage (I love Flash Back in Kensington Market and have gotten most of my cashmeres there) and they’ll last forever if you take care of them. They’re blissfully warm, without being heavy or itchy, and they look great with just about anything, from jeans to leggings to skirts or even layered over dresses.
2. Get a good coat. This truly makes all the difference. It’s up to you whether you want a pretty one that won’t keep you warm as well, or a super warm one that doesn’t look so great (hardly any coats do both). Personally, I love my vintage waterfowl down puffer jacket because it actually manages to keep me warm throughout Canadian winters, unlike every other coat I’ve ever owned… but you might have a stronger constitution and be able to handle some sort of rockabilly wool coat.
3. Get a great, warm, versatile scarf in a color that you love. I have a long purple scarf which my grandmother knitted for me, and it’s perfect and goes with most of my clothes; it’s also long enough that I can wrap it around up to 3 times if I want to bundle up extra tight.
4. Get lots of hats. Wool berets can be found pretty cheaply in thrift stores and vintage shops; I have several in different colors (cream, blue, black, red) and they get a lot of wear, especially on dirty hair days. I also recommend checking out Etsy for slouchy beanies (my favorites are made by Starr Crunch) in colors that you wear a lot. Hats are fairly vital because you lose a lot of heat from your head. When I wear a good knit hat and my puffer jacket, I can be literally sweating while walking down the street in Toronto in January.
5. Make sure you have good boots. This is something you should start thinking about around August, honestly, because it’s really really important and you should be prepared. If you already have boots that you like, get them sprayed, resoled, or whatever else you need to do. And don’t make the mistake of thinking cowboy boots are acceptable snow wear, like I did; they’re not.
6. Update your wardrobe when you start to get bored. I usually find myself hating my winter clothes around January, when I’ve worn all my cute winter outfits several times and am sick to death of cashmere sweaters and thick leggings. That’s when it’s good to go to a thrift store, vintage shop, or even the mall, and stock up on pretty-yet-practical things. New hosiery, dresses, and cardigans make me much more motivated to get dressed.
7. Do a lot of layering. Kneesocks over tights. Cardigans over dresses. Dresses over shirts. Belts over everything. Anything over slips. Layering gives you lots more possibilities and is a way to infuse fun back into utilitarian winter dressing.