These fur-lined boots are my trick for surviving Chicago winters

The products and services mentioned below were selected independent of sales and advertising. However, Simplemost may receive a small commission from the purchase of any products or services through an affiliate link to the retailer's website.

Like many people, I own way too many pairs of shoes, but tend to wear just three or four pairs on a regular basis. And I tend to be fairly selective about my footwear because I live in the Chicago area where we are no strangers to windy, snowy, icy and wet conditions. I like my shoes to be warm, easy to put on and have plenty of traction. Also, I never buy any boots that aren’t waterproof because when could I even wear those?

Over the years, I’ve gone through many pairs of winter shoes before figuring out what I truly wanted — a cute, warm set of boots that was tall enough to get me through most snowfalls but low and loose enough to slip on and off quickly. I discovered my holy grail at Costco by chance. The warehouse chain was selling fur-lined Chooka rain boots during the fall a few years back, and they cost $25.

I liked them so much that the following year, I went back to Costco and got another pair (it appeared to be the only pair left!) even though mine were still fine. I figured I should stock up just in case. Sure enough, that was the last time I saw my new favorite winter shoes there. For my next pair, I ended up having to go to Chooka’s website to buy them for their regular price of $40.

But now they sell them on Amazon, and I just got my last pair there (in anticipation of next winter). You can get a pair of Chooka Women’s Waterproof Plush Chelsea Boots for as little as $25 right now.

I admit, I go through these pretty fast. But that’s because I wear them all the time, every day, literally until they fall apart on me. I’m not sure my coworkers have even seen me in any other shoes (except in summer, when I switch to Crocs).

MORE: The Best Women’s Rainboots

They’re comfortable to walk long distances in, so I’ve logged 40,000 steps in them over a weekend while volunteering for a local children’s hospital. For things like that, they’ve been much more comfortable than my sneakers and even my Nike gym shoes. While everyone’s else’s feet ached afterward — my feet were fatigued, but they didn’t hurt.

Plus, these boots look great with leggings and tunics, my wintertime uniform, and can be dressed up or down. I’ve worn them to meet celebrities, to work and also to walk dogs. They keep my feet dry and toasty all day, and of the pairs I’ve owned, I’ve never had to break any of them in. They’re also fairly lightweight and flexible, yet sturdy. As for fit — I generally buy a larger size so I can put thick socks in (Chicago winters, you know), but they seem to run true to size.

MORE: The Best Boot Socks

If these Chelsea boots have a fault, it’s that they don’t last as long as I would wish. At some point, I wear the back of the heel down, and one pair stopped being waterproof in one spot after just a couple of years. But if I’m buying them for less than $25 and wearing them pretty much all the time through several (long) winter seasons, I have no issue at all with this. Honestly, if they ever stopped making them, I don’t know what I would do!