4 Fall (or Whenever) Ankle Boots I Own & Love

If I admitted to you how much money I’ve spent over the years trying to find boots I liked, were comfortable, were quality and fit well…I honestly couldn’t tell you because I have no idea. BUT, it feels like a lot. It feels like we all have that “thing” that we’re constantly on the hunt for, and everyday leather or suede booties was mine. Specifically Chelsea boots, but I’ve collected a handful over time (and recently) that make me feel like my efforts weren’t in vain.

While yes, it’s still 80-something in LA, and I curse the afternoon heat that turns my bedroom into a nearly unbearable chamber of sweat, I did slide on a pair the other night when it was miraculously cool enough to bear putting my toes away…in socks. And yeah, it felt nice. Like it marked the change of a season, even if it didn’t, and it was just me digging something different out of the depths of my (tiny) closet. I walked out of the bedroom in my casual dress and booties, and, just like I knew he would—as he always does when I wear boots—Charles said “hey, Boots.” He’s not speaking to the shoes, but rather, that becomes my name. He can’t help himself.

So, while four isn’t as sexy an editorial number as say…five or 10, four is what I have to share with you today, in case you’re starting to get the autumn footwear itch and need a place to start looking. Here are a few pairs of ankle boots I own, and love…just like this post’s title would suggest:

Venetian Bootie from Soludos

Anytime I write about shoes, I usually include Soludos. It’s a brand I discovered about two years ago, and have become a repeat customer of. I love their Venetian line—I have a pair of mules as well as loafers from it—and these are no exception. I was blessed with thick, sturdy ankles (a much nicer way of saying “cankles” I suppose), so it’s hit or miss for me whether an ankle boot will extend my calf into a tree-trunk moment or be normal. These fit the normal bill, mostly because of the little crossover action. I have them in tan suede but have been eyeing the grey suede, too. You know…because I go SO many places these days. They look great with slacks, jeans, dresses, skirts…the whole shebang. OH, and my favorite part of Soludos shoes is there’s basically no break-in period. They’re perfect from first wear.

Regan Boot from Madewell

I debated buying these boots for the longest time. I wasn’t convinced that I’d wear them enough for the price, having a heel and all. But then I saw an old coworker show up to an event in them, and I was transfixed by her all night. I know a simple pair of Chelsea boots shouldn’t do that to a person, but she looked AWESOME in them, and I wanted to look awesome, too. I mean…who doesn’t? Luckily, I spotted a sale at the right time and scooped them up for less, though they’re certainly worth full price, tbh. They took a minute to break in the leather of the boot shaft, but that’s also because #cankles, but now they fit like a glove (I have them in black leather). I absolutely never wear these and don’t feel like a powerful bee-yawch.

Sylvie Ankle Boots from Target

If you’ve never bought a pair of perforated boots from Target, now is your chance. I did many, many years ago and I’ve loved them ever since. Their line of Universal Thread boots are SO comfortable, guys. They have memory foam insoles, are really good quality for the price, and sadly, sell out fast. These have a bit more of that pointy look, which you may or may not like, but I find they look good with pants, especially as someone as petite as me. I find sizing a little all over the place, but my standard 8 worked well here.

Everday Chelsea Boot from Nisolo

Another favorite high-quality footwear brand I’ve talked about numerous times. Nisolo shoes aren’t exactly Target-priced, but they take a beating and keep kicking. Plus, they’re a brand I feel VERY good about supporting, for their ethos alone. Anyhow, their Chelsea boot has been in my closet for about three years now and they always feel so special when I wear them. The opening was a bit tight at first around my ankle, but they’ve stretched over time. They actually seem to have changed up the sole a bit since I got them, and honestly, I think that was the right move. Mine was a flat, slick leather sole, while these seem to have more grip. It took a while to scuff up that bottom not to be sliding around every time I tried to walk up my slightly inclined driveway. I find these run a bit small (mine are half size larger than I normally do), but I guess it depends on the kind of sock you choose to wear with them. I have the Almond, but I’ve eyed the Brandy color since the beginning. Maybe one day, I’ll add them to my collection.

And that’s that. Four ankle boots in my closet I can whole-heartedly recommend to you, whether for fall, or you know…all year round. Thanks for being here today!

See you tomorrow, FOAS.