Which Ankle Boots You Should Buy and Why

12 ankle boots for fall

It’s ankle boot season, and let’s talk about which ones to buy for your lifestyle and location!


Ankle boots are my favorite shoe to wear in the winter. They’re easy to throw on with jeans, or wear with a dress and tights, and there are thousands and thousands of styles to choose from.

So which ones do you pick?!

I’ve been getting a lot of questions about styles of ankle boots — which ones are in style, which ones are great for all weather, and how to wear them.


Which trends am I seeing this year?

This year I’m seeing a lot of studs and leopard boots, but honestly a lot of the styles in stores are really classic and chic. It’s a good year to buy ankle booties!


Which ones are most classic?

If you want an ankle boot that will last you for the long haul, pick something in a neutral color like rich brown, black, or light tan, choose an almond shaped toe, pick a mid shaft height, and keep embellishments minimum.

This shape is so classic, and these are waterproof!

Here are a few other great classic options:


Are riding boots still in style?

Riding boots are definitely a timeless style of boot, but over the last few years I’ve seen less and less of them.

Part of this certainly has to do with my location — west coast is much more of a casual style, where riding boots are a preppy style. But regardless of location, they’re definitely not a top trend anymore.

If you own a pair, you can absolutely still wear them, and don’t toss any great quality pairs you might have sitting in your closet (because we know they’ll come back in style eventually), but I wouldn’t recommend going out and purchasing a pair this season.

I’m still seeing lots of over the knee boots, and knee high boots, which we can talk about another day, but I’ve been getting some questions specifically about riding boots so I wanted to mention them.

Here’s a good ankle boot alternative if riding boots are totally your style. These have the same preppy, classic feel, just in an ankle boot form.


Which ankle boots are best for cold weather?

I talk a lot on here about wearing ankle boots, and how it’s most flattering to show a bit of ankle between the boot and the hem of your pants. But when it’s freezing outside, obviously showing your ankles is not an option.

In this case, choose a boot with a taller shaft, and one that is as fitted to your leg as possible. The wider the shaft, the wider your ankles look (not flattering). Lace up pairs like THESE ONES or THESE ONES are great and will keep you warm.

If you need a warm dressy pair, try something LIKE THESE ONES.

If you still want to wear your lower cut ankle boots during the winter, throw on some warm socks to cover up that ankle space. Or wear them with thick tights and a dress.


What is the “it” boot of the season?

Leopard booties. I’m seeing them everywhere right now, and they’re a fun way to add some print and personality to a neutral winter outfit.

Here are a few of my favorite:


Help me style different kinds of ankle boots!

I’ve got you covered! A brand new episode of GET DRESSED WITH MERRICK is coming this week, and I’m talking all about ankle boots and how to wear them! I share them on my Instagram stories (find me on instagram HERE – @Merricksart), so make sure you’re following along so you don’t miss it.


And now… twelve ankle boots in all different styles to help you find the perfect ones for your lifestyle and your location.



  1. Allison says:

    I’ve been looking for a pair of preppy chic booties just like those Marc Fishers! This is super helpful and I love that you included cold weather booties and waterproof. Those are essential in the PNW. xo

    Allison | Peplums & Pie

  2. ciEl says:

    I am looking for a lower bootie to wear with skirts and dresses. Any ideas? I only buy leather.

  3. Nicole says:

    Love the jeans pictured in this post. Are they madewell? I BOUGHT THE black button froNt ones from old navy, but would love to find blue (at a good price). Thanks!

  4. Leah says:

    Can you define riding boot vs knee high boot?

  5. Kimberly Cox says:

    Do you have a link to the ones you are wearing in the first photo?

  6. Lauren Curry says:

    Do you wear socks with Short ankle booTs?

  7. I love ankle boots and I can’t choose my favourite one from your post, all of them look great! ♥

  8. Victoria says:

    Did I miss the part about which ones to wear with skirts and dresses?!

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