10 Winter Ankle Boots I Personally Own, Love, and Couldn't Live Without

Best Winter Ankle Boots



If you live somewhere that actually experiences winter (no offense, L.A.), you know that once the temperatures drop, you’re pretty much living in boots, as far as shoes are concerned. As a New Yorker, my footwear preferences are very specific, as I’m on my feet a good deal during my commute, and after serious trial and error, I’m happy to report that I’ve successfully curated my winter ankle boot selection to be the best yet.

Including trendy boots, practical boots, and everything in between, below I’ve shopped out my top 10 favorite winter ankle boots that I personally own, love, and couldn’t live without for you to hopefully shop for yourselves as well. Every single pair listed below has gotten me through the toughest of weather and the chicest of nights, and if you let them, they will be just as beneficial for you and your winter adventures.

My Top 10 Winter Ankle Boots

I bought these the second I moved to New York and was too prideful to invest in legit snow boots. Thanks to the chunky platform sole and the indestructible nature of this brand, I’ve worn these through rain, snow, slush, and shine, and have never looked back.

These boots are definitely the pair that gets me the most compliments. Everything from the square toe to the delicate bow detail makes any of my winter outfits look 10 times chicer.

I could trek the city for hours in this pair,. For those days when I need boots that look good but can also protect me from everything a New York winter throws at me, these are always my go-to.

For those chilly days when I want to elevate my seventh sweater-and-jeans outfit of the week, these heeled booties are my saving grace. They turn my tired look into something fabulous in seconds.

Not only is this pair one of the coolest that I own, but they are also the most comfortable. The larger square toe and the low heel allow me to walk for miles, and the leather keeps my feet warm.

In case you haven't noticed from my jargon thus far, I tend to lack outfit inspiration come winter, which is why I rely heavily on my footwear assortment to do all the heavy lifting. These multicolor snakeskin boots do exactly that (and have for two seasons now).

Sorry, but I’ll officially never be over cowboy boots, and Havva makes my favorite pairs. These have removable chains so that I can decide to be as extra as I want whenever I want.

So these aren’t the exact Tibi boots I own… The ones I own are now gone due to the fact that I’ve owned them for three years. I wear them so much (in fact, I’m wearing them as I write this) that I’m convinced that any pair of Tibi boots are worth investing in.

These need no explanation—I mean, look at them! I love how high the shaft goes; I never have to worry about my ankles getting cold, etc. 

Last but not least on my list of favorites are these croc-embossed booties. They go with everything, are extremely comfortable, and have now lasted me for three whole seasons.

Shop more winter boots I have my eye on:

Grab these before they sell out. 

I rarely go for light suede shoes, but these really have me convinced.  

The stretch in these makes them ten times more comfortable. 

And now, the boots literally everyone has their eye on. 

These will look so cool with wide-leg tailored trousers. 

Never thought I'd be craving hiking boots but here we are. 

These boots are quickly becoming iconic. 

I have yet to find the perfect platform boots but I think these are the ones.