Before moving to the Midwest, I had an idea of what kind of boots I’d need. Well, I was wrong. After living here for a few years, I have a different idea. Here are the 3 pairs of winter boots you need to survive a Chicago winter (or a ski weekend)!
Before I jump in, let me acknowledge booties. They’re adorable. I love them. However, their lifespan is about 2 weeks in September unless you live in California or Arizona. After that, it’s time to break out the heavy artillery (aka tall boots). I think my booties have seen more time on the shelf than any other kind of shoe since I moved to Chicago.
These are the must have boots to get you through the season! And these are my favorite socks! They are insanely soft!
1. Suede over the knee boots.
Over the knee boots are my most worn type of boot. It’s amazing how warm they are. In my first month of cold climate living, I got to experience the new feeling of your knees being cold. You know, because your puffer covers everything down to mid thigh, shins don’t have feeling unless you’re playing soccer, and feet are protected by socks/boots. Enter suede over the knee boots. Game changer.
The great thing about over the knee boots is that they come at all price points. You can find great pairs under $100, amazing mid-tier options, and of course the coveted Stuart Weitzman. Since I’ve found over the knee boots to be the most commonly worn, I try to have the staples – black and brown, flat and heeled, maybe a bit of grey. My favorite pair are these which come in 2 colors and are currently 33% off! The flat version is also on sale! Here are my favorites!
I have a flat pair and a heeled pair in black and brown!
2. Hunter boots.
Whenever it’s wet and sometimes even when it’s snowy (just not freezing), Hunter Boots are my go to. They’re my second most worn boot. I wear them on the walk to work and sometimes even leave them on in the office. They’re so easy to slip into and out of as well when you need to change into shoes at your desk. The grip on the bottom is ideal for wet conditions and Hunters are lighter than most snow boots so they’re easier to wear in the snow. If you walk to work, this is key! I try to avoid wearing them when it gets too cold because I’ve heard they may crack. A bunch of them are on sale right now too!
I love the packable Hunter Boots because they’re lightweight and great to travel in. They’re also easy to wipe clean after rain, mud, and especially when they layer salt on the snowy streets. I wore them a ton in Ireland! Grab some of their cute socks too!
3. Snow boot.
I love snow boots and thought these would be my most worn. Snow boots and Chicago go together like avocado and toast, right? Not quite. They’re so adorable and on days where there is heavy snow, these boots are life savers. However, what I’ve learned after a few winters under my belt is they are a little cumbersome and can get heavy.
I love SORELs because they’re waterproof while being stylish. A Chicagoan once told me they were the only truly waterproof brand (even though other brands say they are).
4. Going out or date night boot.
The most challenging thing for me was figuring out what to wear when we go out. Aside from black over the knee boots, I find myself wearing short boots with leggings too. These are my personal favorites (so dang cute and 3e% off!) along with these wedges which are insanely comfortable and waterproof!
As basic as these are, I love Uggs because they are so darn comfortable. They can take a beating and survive the salt on the roads. Plus, the insides is plush and they’re really warm. They are perfect for slipping on on the way to a work out or running errands. I’ve had these Uggs with the buttons through 2 winters!
What is your favorite pair of boots for winter? What kind of winter boots do you wear the most?