I'm a Chicago dog walker in the Old Town Neighborhood, 60610 and it's starting to get cold again. So as a dog walker, how do you survive the the lovely gift of freaking cold that our Chicago thoughtfully throws in our faces each winter? That Chicago wind is a beast with a mind of it's own. I will let you in on a secret though. The winter dog walks are not that horrible if you are prepared and dressed correctly.
I like to wear a long sleeve shirt, sweatshirt, big down coat, leggings under my jeans, thick socks, thick boots with great traction and a furry lining, a knit SIT beanie, gloves, and occasionally a face mask. So just those few things, but really, all of those layers make a walk so much more doable and enjoyable than without them. A lot of times I even get hot in negative degrees because I'm speed walking everywhere. You can also buy these Heat Factory disposable warm packs. They are these wonderful little packs that you activate by pushing around the material in your hands until they heat up and keep your hands warm. You can also stick them in your shoes, but I like to keep them in my gloves.
Now as far as specific boots, I would suggest investing in something waterproof, very warm, with great support, and a boot that you can either slip on and off or one that has a zipper. You don't want to have to keep untying your boots every time you get to a client's door. An amazing place to look for such amazing boots for good prices is Alamo Shoes.
Also, no one wants to take off their gloves to take a photo of each dog and send an update when it's negative degrees outside and the brutal wind is zooming in on your bare unprotected hands. So wear those thin gloves that allow you to use your touch screen phone underneath your super warm gloves. This will make you much much happier.
Also bonus tip. I'm assuming that when it gets freezing cold, you can use your car as a refrigerator and bring a lunch that won't spoil! Yay homemade lunch!
So I hope this helps and stay warm out there fellow dog walkers!