Dress in layers. Lots and lots of layers.
To go to the office today, I add a pair of wool tights under my slacks, and put on my warmest sweater (the one with both wool *and* Angora in the yarn) over a turtleneck. (Turtlenecks were very popular at the office today.) Over my tights, I put on a pair of thick wool hiking socks just for the commute. Before going outside, I add the outer layers: a wool/cashmere blend cowl pulled up over my mouth, 3/4 length down coat, shearling hunter’s hat with ear flaps down, and a pair of thrummed mittens. (If you’re allergic to warm animal fibers like wool, alpaca, and Angora, I feel very sorry for you.) Pull up your hood if you have one; you want to block out as much blowing cold air and snow as possible, but also be careful when walking with your hood up as it limits your peripheral vision. (And as a driver, be aware that people bundled up so much have issues seeing you, so slow down!)
Wear sturdy, water-resistant boots that cover your leg to mid-calf (at least).
Unless you are a small child and can be carried around, you will need to deal with this when you encounter it.
Not all taxis or cars pull up flush with the curb. If you’re taking public transit or spend any time at all walking anywhere, you will undoubtedly ruin your expensive fashion boots in a month. Forget Uggs (or Ugg-like footwear) and dressy “riding boots.” Think Bogs, Kamik, or Sorel. Tuck your pants into your boots so they don’t get wet and salt stained. Stand back from the curb when there is a pool of slushy water near it. Passing cars and buses have been known to splash that junk over the lower portions of pedestrians who are standing close to it.
In the neighborhoods, beware the sidewalks.
Some property owners are jerks and don’t ever shovel their walks. (Yes, it is the law but there is no enforcement of the fines.) Others are not able to shovel early in the day, so you will likely need to slog through snow on your morning commute. Even attentive shovelers can’t always keep the sidewalk clean enough that it doesn’t have the occasional icy patch. Freshly fallen snow over ice can lead to some really ugly consequences, so learn to shorten your stride and distribute your weight more evenly over each step. In other words, walk like a duck.
I left the house at 6:30 this morning and only one place had its sidewalk clear at that hour. I mostly walked in the street, despite the traffic. Chicago’s major streets are *always* well attended because we kick people out of office if they don’t keep the streets clean in winter. (Too bad we are inured to corruption and don’t demand more honorable behavior from our politicians, just snow-free streets.)
In the business district, beware the buildings.
It’s uncommon to get hit with ice falling from the tall buildings, but there have been enough incidents that these signs spring up all over the Loop during winter.
Take enjoyment from simple outdoor activities, like shoveling.
Maybe you are a renter or live in a condo so you think you won’t need to clear snow. If you own a car, though, you will need to shovel at some point. Maybe you’re even lucky enough to have indoor parking. You can still get stuck driving down a side street before it’s been plowed or getting out of your garage into the alley. (The otherwise excellent street plowing crews deal with side streets last, and don’t do alleys at all. Chicago instead lets the garbage trucks “press” the snow down in the alley as they collect trash, which is the closest they come to plowing them.) Or maybe you’re tired of hearing someone spin their wheels helplessly over and over and over again as you’re trying to concentrate on a book or go to sleep, so you throw on your many layers and water-resistant boots, and go out to help. Either way, you may need some ibuprofen and Icy Hot (and perhaps a slug of whisky) at the end of the day.
Learn about “dibs” and be wary of those who tenaciously cling to it.
Yeah, it’s not legal but you don’t want to be the victim of retaliation. This could include getting chased by someone wielding a shovel if you so much as touch the stuff marking a dibs spot. More ominous things like a busted windshield have been known to happen.
Look for the “silver lining” in the weather.
“Six more inches of snow on the way? At least it’s warm enough to snow!” (An actual quote from a friend.)
“Single digits and below zero wind chills? At least it’s sunny!” (A quote from another friend.)
“The temperature is going to be 3 with a wind chill of only -20 tomorrow morning? I can deal with that.” (I said this to B last night.)
“It’s above freezing AND sunny? OMG, it’s a miracle!!” (Or it’s April…possibly both.)
Move to California.
And although it’s not strictly about winter, there are many winter anecdotes on this list.