3 Basic Booties for Fall & How to Wear Them

by Ashton - November 24, 2020

The best part of fall and winter is hands down the boots. I have a slight obsession with ankle boots and pretty much wear them year-round. I have at least two dozen pair (I know, I know), but for my daily casual style I tend to stick with the same three pair: brown, black, and taupe. And yes, they are the exact same boot in a different color.

If pressed to whittle down my collection to just a handful, these three would be the ones I would keep. If you're wondering why I, the queen of patterns and unexpected add-ons, would choose to keep the three plainest pair of ankle boots I own, I don't blame you. So let me tell you what makes them the obvious choice.

They've got a classic cut that will never go out of style.
The block heels are just high enough to extend my leg line but not so high they're uncomfortable.
They are at once understated and elegant, especially the black pair.
Between the taupe, brown, and black, I have a pair of boots that go with literally everything in my closet.

This is the second year that I've had these particular pairs of ankle boots, so they're no longer available. They came from Old Navy and are pretty good quality for the price. I've rounded up five similar options for you guys below (two with lower heels since I know not everybody likes to add to their height). Most of them come in at least two color options. Just click on the pictures to see them.

So now that I've told you why you need some basic booties, let's talk about how to wear them. To be honest, I really don't have any rules per se that I follow when putting together an outfit with ankle boots, but I can give you a few guidelines to help you create a look that feels more put together.

Don't pull the hem of your skinny jeans down over the boot shaft. They're called ankle boots for a reason, so show some skin. It doesn't have to be much, just a sliver will do, but having that separation between the boot shaft and the hem of your jeans makes a huge difference. Check out this post for some suggestions on how to roll your skinny jeans. The same ideas work with boyfriend jeans, as well.

If you insist on your ankles not showing, try a pair of bootcut jeans instead. If you really want that skinny look, try jeggings or leggings and tuck them into the shaft of the boot. Make sure they're tight and long enough so you don't get bunching around your ankles. Don't like either of those suggestions? Grab a cute pair of crew socks (or a pair of thicker socks that you can scrunch up) to cover any exposed ankle.

Skirt and dress length does not matter. If you're concerned with showing a lot of bare leg, wear tights!

Those are really the only "rules" I stick to with my ankle booties. If you're still not sure, this is a great resource for how to decide what booties to wear with different bottoms. It's very thorough and covers everything from skinny jeans to non-skinny jeans, skirts and dresses, and even workwear.

Now, on to some outfit ideas from yours truly. A lot of these outfits are old (read: last year) since it really hasn't been that cold here yet...and I've been wearing my sneakers more than my boots since we've been sticking closer to home than usual. If you've got questions about any of the items shown, shoot me a message and I'll share the link or something similar!