Most Helpful Guy
I live in Florida so I don't really encounter this problem very often. I think the main thing is to use several thin layers of clothing rather than one thick layer and to use insulated boots.
Most Helpful Girl
I live in wisconsin and it gets reeeally cold here. Since it isn't quite cold enough yet to bring out my giant winter coat, for now I just wear two decently-thick sweaters. You could try that out. Also if you wear leggings or tight pants (jeans), slip on some heavy sweatpants and put them over your normal bottoms. At least until you get to where you're going. Then you can just take off the extra clothes and put them in a bag or something. Don't forget to wear two or maybe even 3 pairs of socks. Your hands and feet temperature can make the rest of your body feel a lot colder than it actually is. Also, always have gloves or mittens handy. If you won't be using your hands a lot, you can always put on gloves then add mittens over top. Layers are the best :) Always have a scarf to cover up your face as much as possible. By breathing into the scarf you can usually heat up the rest of your face a bit. Lastly, always wear a hat, earmuffs, or a warm headband. If your ears get too cold, it can be really painful. Hope this helps :)