Things I've learned in my first winter.

1) Check the weather forecast.  Every day.  This may be hard to get used 
to, but in a cold-weather climate, the weather forecast ACTUALLY MEANS 
SOMETHING.

Additionally, it's impossible to tell by looking out your window, without 
practice and experience, what cold weather is going to do.  If you're 
reading this, you probably don't have it, let the weathermen do it for 
you.

Good sources of weather:

2) Cover your face, head and hands!  You can go outside for longer in a 
long-sleeved tshirt if your extremities aren't sending alarm signals to 
your brain.  I taught myself to ride any bicycle hands-free because I 
often forgot to grab my gloves when I left the house.  Something along the 
lines of, "my hands won't get cold this time" or, "it's only overcast, not 
snowing, so it must be a lot warmer today."  Falsehoods!

3) Stay dry.  You can no longer just run out of the shower, and let 
yourself air-dry.  You will air-freeze.  Towels, hot air blow driers, make 
use of them.  Cut your hair if you want to get out the door faster.

4) Get good shoes.  Waterproof boots are where it's at.  Little is more 
unpleasant than the feeling of your sneakers wicking up cold street 
puddles, and thermocoupling your toes to ice water.  You don't want to 
donate your feet to be ice-water absorbers, you will be only able to 
think of one thing - getting a dry pair of socks on.

5) Eat good hot food, drink warm beverages.  You will feel tired and burn 
out faster than a fire in the rain if you stick to candy bars and soda. 
Plus, it can truly be a joy to clutch a piping hot steamy mug of 
peppermint hot chocolate, while ignoring the slush falling into your 
shoes.

6) Clothing - wear something you can take off.  The concept of layering 
was confusing to me, at first ("how many do I have to wear, to be properly 
'layered'?" "does a bra count?").  The two best pieces of advice I got 
were first, to wear long underwear - and not cotton, but silk, for two 
reasons;:  cotton gets wet.  If you're over-warm, and stuck in long 
underwear, when you next go outside, you'll be in col, unpleasaant 
underwear.  no fun.  Silk is extra thin, tight on your skin, and retains 
heat pretty well.  The second was to wear a spaghetti strap or camisole as 
the first shirt-laye, and use jackets, sweaters, and cardigans for layers 
after that.  This allows you to really cool off, if need be!

I've never really had a problem with pants, as long as they kept dry 
(consider bike chaps, if you're going to bike in wet weather (slush, rain, 
wet snow)).

Hats, and earwarmers can really make your experience more pleasant!

7) acclimatize.  All of a sudden, chapstick can actually help you - if 
you're from a humid climate, chapstick is like eating an especially 
buttery roll.  In the cold, it will get dry, and your lips will get 
irritated and crack.

Also, if you're from an island like I am, your whole sense of distance is 
likely to change.  A far walk is an even further walk, in the cold.  A 
driving distance becomes a walking distance, which becomes a far walking 
distance.

-Star