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A Good Pair Of Ankle Boots Never Go Out Of Style

The hardest working pair of shoes in your wardrobe.
by In The Groove October 10, 2025
A Good Pair Of Ankle Boots Never Go Out Of Style

It doesn’t feel like fall until I pull out my favorite ankle boots. Year after year, they never go out of style. Whether you’re sticking to the classic black boot, a trendy kitten heel, or switching it up with brown suede, our guide to fall ankle boots will help you find the right one. 

From September to March, my black ankle boots are probably the most worn item of clothing I own. I end up reaching for them for date night, for TK, or just when I want to feel a little more put together. So I feel good about investing in a nice pair, like the incredibly chic Stretch Boot from fashion world favorite Emme Parsons. I love the distinctive heel on Staud’s Wally boot, and the classic appeal of Stuart Weitzman’s stretch leather boot.

But! You don’t have to shell out a ton of money to get a great look. J.Crew gets a lot of love, but I think their shoe selection is underrated. I really love their Stevie boot, which has just the right amount of polish thanks to the pointy toe and kitten heel. It comes in suede or leather, so you’ve got options! Madewell’s boot selection is really versatile, whether you want a shorter boot length, some cowboy-ish flair, or some patent leather shine.

An ankle boot doesn’t have to be boring either! You can switch it up from the usual black leather for a more subtle statement, like this gorgeous patent-leather croc pair from Mango in a delicious chocolate brown color. Brown is a more versatile color than you might think, and it’s really versatile in a different texture. Like suede! I love the Western-inspired details of this Steve Madden boot, Madewell’s pointy-toed kitten heel, or this square-toed option with a comfy block heel.

Shop the rest of our fall ankle boots edit below: 

All of our recommendations are curated by Susan & the In The Groove editorial team. In some, but not all cases, we receive a small commission for leading you to what, how, and where to buy all this wonderful stuff.

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Comment PODCAST, and we’ll DM you this episode of Comment PODCAST, and we’ll DM you this episode of @sowhendoi. This week, we’re talking about something we all swear everyone else is worse at… but secretly know we’re guilty of too: our relationship with our phones. From scrolling at dinner to checking texts mid-conversation, we unpack how technology is quietly shaping our relationships, attention, sleep, loneliness, and even intimacy.

We talk about why being present might be the ultimate luxury, the small “baby steps” we can take to reconnect with the people right in front of us, and the simple habits that can help us feel more intentional in our relationships again. If you’ve ever felt distracted, dismissed, or wondered when we all forgot how to just be with each other, this one’s for you.

https://podcasts.apple.com/us/podcast/so-when-do-i-take-my-clothes-off/id1872500053?i=1000769326702

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