Wear it Wednesday | Ankle Boots for Fall 2020

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The most fall-inspired piece in my wardrobe sans cardigans would have to be ankle boots. They are perfect for keeping your feet warm and dry on cool days, away from snow or puddles, stylish and very functional. While I could sing praises of ankle boots all day long, I have friends who still aren’t quiet sure what to do with ankle boots, or if they can even pull them off. (Anwser: yes you can and I promise!) While I only own 2 pairs of ankle boots, between the two of them they go with everything in my closet. The trick is knowing what kind of boot is best for your style and what color to go with!

TOMS Lelia Ankle Booties

I snagged these on Poshmark several years ago, I had my heart set on them but didn’t want to pay full price. Anyone else ever feel that way? So I waited until I found my size and my color on the secondhand site. These ankle boots feel much more fancy than the TRC pair, which I’ll share later in the post. They have a higher heel, a tassel on the back zipper, and a more almond style toe. I prefer to style these with my full length skinny jeans, because my jeans end at the top of the boot and make a seamless transition to the boot shaft. Even though these boots are a beautiful shade of cognac, they go so well with black and grey. In fact, there isn’t much in my closet that I won’t pair with these boots. I think they are more versatile than my black pair!

This pair of ankle boots is also has a higher heel, probably the highest in my closet that I can comfortably wear 2 1/4″ stacked heel. Since this pair is more cheaply made, I don’t worry about them in the winter as much. They claim to be leather and if they actually are they are thin and lined on the inside, this pair also has rubber soles which I feel more confident walking in on snow and ice.

The Root Collective Black Ankle Booties

I would normally write the style name of the boot out, so if you love it you could get yourself a pair but I have to be honest. This pair of TRC boots are one of a kind. I snagged them from Bethany herself back in 2017, they tried a new leather and it came out too shiny for their taste. So, I have been quietly rocking one of a kind boots for a few years now. This pair is cut similar to The Root Collective ESPE Boot without the cloth back strip, 100% made in Guatemala and lovingly worn for the last several years. Honestly, I feel a little awkward in these boots, the front of the boot comes up higher than I’d honestly like but I love the low heel. This boot is more like a chelsea style ankle boot than a fancy heeled ankle boot. I especially love to wear this pair of ankle boots with cropped denim and my favorite pair of boyfriend jeans.

I’d love to add a pair of the Lee or Blythe ankle boots to my closet in the future, I love the notched style which I could probably pull off for more of the year. And in case you are wondering, I’ll take a pair in chesnut, size 6 please. 😉


After writing much of this post, I was suddenly inspired to go condition my boots. Imagine that! Which I haven’t done in a LONG time. Probably since about May of this year. I try to condition them just before summer arrives and they go into hiberation in the closet. So, September seems like the right time to condition them again before the fall season.

Which pair do you like more? The taller heel and rounded toe of the Toms boots or the more casual low heel and point toe of The Root Collective pair?

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