Black Ankle Boots That Stand the Test of Time

When I shared tips on how to style millennial booties, I was asked to share some quality black ankle boots that stand the test of time. Boots that are stylish now, and with regular care, can still be stylish years from now. Throughout this article I share my personal favorites.

Stylish & Timeless Black Ankle Boots

In no particular order, eight of the most stylish & timeless black ankle boots with my tips for shopping for such footwear. I also share a few other great options at the end of this article.

It is impossible to know what will be fashionable in a decade. Fashion trends are are often determined by social and political events. For example, the popularity of sneakers beyond the gym and track was due to 9/11; women wanted shoes that could help them escape. Athleisure and elevated sweats gained popularity thanks to the pandemic, and for over a century we've seen hemlines rise and fall with the stock market.

That being said, there has been a certain type of black ankle boot that has been fashionable for over a decade and doesn't seem to be losing style steam.

You want an ankle boot made from genuine leather, and preferable not bonded leather (though these days it's hard to know offhand what kind of leather you're getting). Genuine leather will mold to your foot, can be polished and maintained, won't get as stinky and sweaty, and will hold better to the soles.

A smooth finish will be the most versatile. Steer clear of tumbled leather, nubuck, suede, glazes, skins, and any sort of finish. Smooth leather can dress up or down and can be polished back to original finish.

You want at least a slightly elongated toebox. A longer toebox feels more fashionable even when the trends change. No need for the toe to be pointy, you can go almond, square, pointed, tabi, whatever floats your boat as long as it's not a short or snub toebox.

The sole and the heel should be black. No contrast stitching, no layered sole of different colors or materials. If the heel isn't solid black, it should be artistic and architectural so it makes a statement and becomes a signature piece of your style. Unless it is architectural or artistic, steer clear from platforms and wedges and stick with more sleek of soles and classic of heels.

With zippers, unless it's artistic and statement making, it should be black and subtle. Same if there are any elastic gussets. Hardware should be minimal to non-existent so the boot isn't specific to any era or level of formality.

I hope this helps. And while these are some of my personal favorites, they are not the only options out there for stylish black ankle boots that will transcend trends at least for the next several years.

Shop My Picks for Stylish & Timeless Black Ankle Boots: