Cute Ankle Booties

Okay. Honestly? I didn’t like these the first time I saw them. But then I really loved them. Kind of out of the blue. One of the girls in our office has a pair of black ones and oh, they’re cute. She totally convinced me that they’re perfect for the winter months!
Now that it’s getting much (much) colder, I wear my riding boots nearly every day. They’re perfect for a lot of my outfits, but sometimes I want something a little bit different. I think the ankle bootie is going to be just that. I think they’re going to look cute with everything from adorable dresses and tights to skinny jeans and chunky sweaters.
The crazy thing is that the boots are literally everywhere. From Zara to Old Navy to Nordstrom to J. Crew and a ton of other places. The prices are pretty all over the place as well. This is great since there is really something for everyone. And they come in a bunch of different colors. I seriously can’t decide between leather (real or otherwise) and suede…. and even the colors!
From top to bottom:
Which pair would you choose?

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I like my ankle boots, but I know as soon as it snows they will be going into the closet. Once the snow starts sticking it becomes slippery to walk in them and snow often gets in. But they are great for fall weather and a night out. I love them with dresses.


Check out DV Dolce Vita's Dakoda boot at Nordstrom.. these are the ones I have and they have an adorable back zipper lined with cobalt suede (orangey red for the black)! I like to leave them slightly unzipped to show off the blue.


I was hesitant about the ankle booties at first too but now I love them! I really like #9 🙂



I can't wait to see how everyone votes, because I am having the same dilemma. I think I like the Sam Edelman the best, #7? But I think I like the taupe color. I love the Anthropology, but do not like the colors. J Crews are cute too, but I cannot justify the price and am not sure about the colors.

The F Spot: Fashion Blog

Dear Carly,

I need to get something off my chest. I absolutely adore your taste in just about everything…except riding boots! Although I've tried avoiding the subject, I'm broaching it now because the link to your Sept. 18th post brought back memories of an entire Saturday afternoon spent comparing hardware and leather.

As much as I love Tory Burch, I wouldn't recommend her boots to anyone. Perhaps the Tories you own are of a higher quality leather. But this year's Tories are thin, flimsy, too shiny; orange-y in color as opposed to a deep, rusty cognac; and lacking in shade variety, as opposed to the natural, sultry ombre of high quality leather. And the worst part about the boots is their hardware–cheap, shiny gold Ts that advertise the brand more than the craftsmanship (which, apparently, is not something they should advertise). Most strikingly–and this is definitely something I wish you'd address on your blog–they are made in China!! $500 for a pair of boots made in China?

Please don't take this personally, as I'm a bit priggish about boots. I guess you can call me a boot snob. In my opinion, boots, especially riding boots, should be an investment. That said, I bought a pair of cognac-hued Fryes, which are by far the better option in this price range. The leather is thick, variegated, and unsupported by fabric lining. I detest fabric linings, as they are usually there to support a thin, flimsy layer of leather. Manufacturers tend to use millimeter-thin leather for boots and then call them "leather boots."

The second option is vintage. No need to go into detail here, as we all know the world has changed. We used to value craftsmanship over brand names.

The third option is to capitulate to the fashion industry and buy a pair of high-quality, yet overpriced boots. In this case, I would suggest Burberry, as the brand has been around since 1856 and, in my opinion, its quality can be trusted.

Another option is buying a pair of real riding boots from an equestrian shop. In this case, I would suggest
The Equestrian Shop even carries real wool fox hunting jackets–very preppy!

I hope this doesn't offend you! As I've said, I adore your taste. But please keep quality in mind! That's what being preppy is all about.


I agree, they are everywhere! There is the most gorgeous pair of suede chunky heel boots with gold glitter that's on my Christmas Wish List. They are extremely sturdy looking, seem easy to walk in and will match just about everything. I love being able to choose from different price points and styles.

Alice Hicks

Hi! Maybe it’s a nice thing to do an article on how ankle booties were in fashion from 2012-2017 and now they are out-of-style? With the demise of the tapered/skinny jeans in 2018 and bootcut/flare back, now no one wants to wear ankle boots anymore.