Dress Code: How To Survive Your First Winter


“I just moved to Chicago from a warm climate,” a reader wrote. “What do I need? Help!” We’re glad you asked!

First of all, don’t panic. Cold weather’s, well, cold; winter clothes are expensive; but, with just a few basic purchases, you should be able to embark without fear. Here’s a few items that should help you get started. And for expert advice, I called on Anna North, a lifelong Californian who made the move to snowy Iowa.

Long Underwear
In silk or thermal, a set of long underwear will prove invaluable on really cold days. The silk kind is especially thin, making it easy to layer under pants. Anna is an advocate of leggings, saying, “Long johns are probably more effective, but I find them kind of hideous and am embarrassed to take off my clothes in front of anyone if I’m wearing them. Solution, for your sex life and your warmth: leggings. Put them on under your pants, pull your (warm) socks up over them if they’re short, and you are ready to go. Even in -15 degree weather this method kept me pretty warm.”

May seem obvious, but tights are a versatile lifesaver. Get a few heavy wool pairs to wear with skirts, and keep in mind that in a pinch, tights — especially thinner ones — can do the job of long underwear. On really cold days, some of us have been known to layer multiple pairs.

A Serious Coat.
Says Anna: “You need a new coat. You might think you can just layer stuff under your cloth coat or leather jacket but trust me, if the temperature is going to be going below 10, you need down. And you need long — preferably something that goes down to your knees. I thought I could get away with a short coat my first winter in Iowa, and on the first really cold day I tried to walk about three-quarters of a mile to an
academic building. By the time I got there I could not feel my thighs. But I was far from home! It was getting dark! How was I going to get home without losing my legs? Solution: I went into a public restroom,
took off my pants, wrapped toilet paper all around my legs like a mummy, pulled my pants back on, and went out into the world. This actually worked okay, and I recommend it in a pinch. But seriously, get a long coat.”

I’d add: if you are only getting one, you have a choice to make: a wool guy that looks respectable, or a serious down parka. Ideally, you’ll have both. Don’t feel like your coat needs to be a big investment piece: thrift stores and even places like H&M and Zara are great coat resources. If you’re going to get just one? That’s up to you, and the climate. If you’re somewhere seriously snowy, down is non-negotiable. But if you have one more tailored wool guy — big enough to layer under it — and a serious parka, between the two you’ll be effectively covered.

Down vest
I’m not talking some lumberjack special, but rather a thin down vest that you can layer — particularly useful under that wool coat. This will practically double your warmth quotient.

Warm socks
Learn it, love it, live it: you want a few pairs of heavy wool socks — and long enough to pull up over long undies and leave no room for cold to get in.

While big woolly sweaters are great but if you’re only getting a few, then thinner ones are the most practical: cashmere is super-warm, thin enough for the office and easy to layer. Also, not the investment it once was. Thin merino wool is a good alternative.

Snow Boots.
Says Anna: “The boots and shoes that you have WILL NOT CUT IT. You will come back from California one New Years Day and think you can just walk to dinner in the snow in your Chucks and then your feet will go
completely numb and you will have to go to the bathroom and pour hot water all over them in order to reassure yourself that you don’t have frostbite (note the public restroom theme here). Nope, you need some lined boots that are at least somewhat waterproof, because you will be walking through snow and if you are just wearing sneakers or leather boots, it’s like your feet are IN THE SNOW.”

If you’re somewhere snowy, serious boots with treads are another non-negotiable. These can be expensive, and for the past few years, I have found a cost-effective solution. Hunter makes fleece liners that are intended to fit inside their wellies. They’re about $40, but they fit inside any inexpensive rubber boots and turn them from iceboxes into cozy, waterproof snow boots. Maybe not the chicest, but cheap, warm and effective.

Other Boots
Besides snowboots, you’re probably going to want another pair of high boots that you can wear to the office, and wear on non-snowy days with your woolly tights and maybe a pair of those heavy socks. The heel height is up to you, but a pair wide enough to fit over jeans makes a big difference; in a cold climate, you’ll live in your boots. I have never bought these new, but always get them on eBay or in thrift stores — then have them waterproofed and soled.

Scarf, Gloves and Hat
Personally, I have two sets: cuter ones, and then the heavy-duty stuff for snow (think waterproof gloves.) Also, I’ve recently started boldly using mitten clips, which I totally recommend for adult use. People will fear and admire this. Places like Filene’s, Ross or any discount retailer are great for good-quality accessories like leather gloves. Personally, I am addicted to leather gloves lined with cashmere, which I have only ever bought used online. I am also convinced that keeping gloves on in the subway lowers one’s incidence of catching colds tenfold.

Sweater Dress
Hardly an essential, but I find myself reaching for this more often than I do anything in my closet — a lifesaver when you need to look respectable and it’s freezing. Get it a few sizes big, and you can layer!

And now, arctic ‘belles, let’s hear from you! Can you top TP? Freezing transplants need to know!

For all of our handy Dress Code guides, go here.

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