15 Cute Outfits With Ankle Boots

Hello lovely! With fall not too far around the corner, I’m really excited about this post because it’s about one of my favorite shoes: Ankle Boots! 

I remember talking to a girlfriend about ankle boots I was shopping for, and she had mentioned how it was too hot to be thinking about wearing ankle boots, yet because it’s still summer, I explained to her that ankle boots are great all year, and they come in a ton of different colors and styles. 

So then I thought…well, if my usually fashion forward girlfriend is confused about these boots, maybe others are too! So in this post, we’re going to look at cute outfits (for all seasons) that include wearing gray, black, and brown ankle boots!

Cute Outfits With Gray Ankle Boots

Gray ankle boots are much easier to style than most realize. They’re sort of an underdog in the shoe department, which is a shame because they really are a neutral color and can bring a lot to your look. Here are 5 examples of cute outfits you can wear with gray ankle boots!

1. Gray Ankle Boots & Matching Cardigan

This is probably one of the simplest outfits out there, but it looks so good.  The trick is the gray cardigan that matches the gray ankle boots! This is a simple fashion trick that works for any colored shoe you’re wearing! 

A pair of jeans and a white v-neck tee are staple wardrobe pieces. These boots are cute with their little cut out and extra embellishments, too!

2. Gray Ankle Boots with White Midi Skirt

Here is a super cute way to wear gray ankle bootsㅡwith a midi skirt! This is a modest and sweet way to wear ankle boots while wearing a white skirt and matching gray sweater. This could be a great outfit to wear to work, church, to a brunch date with friends, or even as a normal day’s outfit!

3. Gray Ankle Boots with Light Wash Jeans

These light gray ankle boots look great with her light washed, slightly distressed skinny jeans. I can really appreciate the dusty brown-ish rose color of her sweater with the light wash jeans and boots. It’s a soft look, and I’m all for it.

A trick to giving your outfits a little extra pop: slightly roll up your long sleeves and add a watch or bracelets! Check out how you can Wear Multiple Bracelets and Rock the Look!

4. Gray Ankle Boots with Fur Coat

Disheveled outfits are popular in fashion thanks to celebrities like the Olsen sisters. Something about putting all the right things together in a way that isn’t all the way put together actually looks good. 

So in this outfit, you’ll see gray chelsea boots, skinny jeans, an oversized shirt or this could possibly be a t-shirt dress to get the length underneath a faux fur coat, and a matching gray studded purse. If you weren’t into the oversized shirt, you could swap it for a plain or graphic tee!

5. Gray Ankle Boots with Jeans & Checkered Shirt

Checkered shirts are really great to style with your fall outfits. Channeling the inner lumberjack, I guess? Whatever it is, they’re awesome. A blue checkered long sleeve is easily worn with denim skinny jeans and a pair of gray ankle boots.

Cute Outfits With Black Ankle Boots

Black ankle boots are probably the boot that would work with every outfit you wanted.

6. Black Ankle Boots, Black Jeans & Black Graphic

Here, you see a super edgy, street look, featuring black ankle boots, black, high-waisted jeans, a black knotted graphic tee, and a black purse. If you weren’t sure how to wear all black in a casual way, this is it. 

The graphic is where you can add pops of color, and if you wanted, you could bring more in with a colored bag.

7. Black Ankle Boots with Fishnet Socks

Wearing an oversized tee or sweater as a dress is a great opportunity to wear ankle boots. This outfit here actually shows fishnet socks above it which helps visually. Without those, you see a hard start or stop of these bold, black ankle boots.

I love the addition of the big faux fur jacket. It makes the outfit look expensive.

8. Black Ankle Boots with Trench Coat

These boots are really great for fall and winter too. I actually love wearing outfits similar to this one, with a boot, denim, sweater, and long coat. You basically can wear any shirt you want with a look like this.

Check out my Long Teddy Bear Coat OOTD for another example of wearing black ankle boots with a long coat!

9. Black Ankle Boots with Black Leather Mini Skirt

Definitely wear your ankle boots all year round, though. 

Look how great these Chelsea boots look with a leather skirt and a lace up collared blouse! This is an outfit that can be worn for so many different reasons. Work, nights out, days running errands, parties, anything you wish, where a leather mini skirt is acceptable.

10. Black Ankle Boots with Black Pleated Skirt

Just like with mini skirts, these boots are great to wear with midi skirts! I love pleated skirts. They’re so fun. This is a cute way to wear a simple graphic sweater with a pleated skirt and black vinyl ankle boots. By the way, these ankle boots are super cute with the studs across the sole!

Cute Outfits With Brown Ankle Boots

Brown boots look really great with denim, there is no doubting that, but they actually style well with black pants! Of course, other colors too, so I wanted to show you some cute ways you can wear brown ankle bootsㅡespecially for your fall looks!

11. Brown Ankle Boots with Mom Jeans

I keep showing you these long trench coat outfits because they’re really popular go-to looks during the fall and winter. II want to make sure you have all the inspiring looks for it! (Plus, I love my long coats!)

12. Brown Ankle Boots with a Dress & Cardigan

Tights are a fun addition to outfits, especially dresses and ankle boots! This is a cute fall look, and I love that she’s matched her boots to her belt and bag, plus, her cardigan is a similar color too. I’ve heard women say that brown and black can’t be worn together, but that (obviously) isn’t the case!

13. Brown Ankle Boots with Red Plaid Scarf

A classic fall look right here, with cute brown boots, denim skinny jeans, a white tee, brown cardigan, and a red plaid scarf. You could have a lot of fun with the colors and patterns of scarves in outfits like these. Adding a beanie would be adorable, too!

14. Brown Ankle Boots with Checkered Blazer

Here is another cute example of wearing ankle boots with a denim skirt like the OOTD I shared with you with black ankle boots. 

This is fun because she’s draped a checkered blazer over her shoulders, and it really ties in the colors of her boots and her blouse.

15. Brown Ankle Boots Leather Leggings

Leather leggings are super cute with boots, and as you can see here, they look really good with her brown ankle boots and a cream, off-the-shoulder sweater! This is another outfit where it is really clear that brown and black do go well together. 

Check out my style guide on wearing leather leggings for more on those!

Alright, if there is anything you took away from this post, I hope it is that ankle boots (no matter what color they are) can go with the simplest of outfits. They can dress up any pair of jeans and a shirt, which means there is no reason to not have a pair of ankle boots!