10 Ways to Wear Flat Ankle Boots With Anything
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  • Writer's pictureBrenda

10 Ways to Wear Flat Ankle Boots With Anything

Updated: Sep 21

Flat ankle boots are generally seen as more casual due to the lack of heel but that is not necessarily the case. Flat booties could be styled up or down to achieve either a casual look or a more formal one.

The color, shape and style of boot would determine how it can be paired and my job today is to bring you as many of these options as possible. If you’re looking for some major inspiration on how to style a pair of ankle boots, then you’ve come to the right place!


You may want to check out my post on how to wear flat ankle boots with jeans if you are specifically looking for inspiration on how to rock your booties with jeans. This post would be more broad with the outfit selections.

Ankle boots are definitely a fall staple and if you live in a country where temperatures tend to drop, then you understand where I’m coming from. They are easy to wear and easy to style as you don’t have to worry much about tucking clothing items into them.

Before we jump into the different ways to wear flat ankle booties, I would like to share my absolute favorite flat ankle boots I’m loving at the moment along with wear you can find them. These boots come highly reviewed on the various platforms and I’m including booties in different price ranges, depending on what your budget is like.

Disclosure: This post may contain affiliate links, which means that I get a commission if you decide to make a purchase through our links, at no cost to you.

Where can I get the best flat ankle boots?

1) DSW

I love DSW not only for their wide variety of shoes but also because they cater to women with wider calves and wider feet. I always head to their website first when I’m looking for a particular type of shoe. I also appreciate how quickly they are with restocking styles.

My favorite flat ankle boots currently for sale would have to be these flat Doc Martens and for a dressier look, these brown ankle boots by Vince. Chelsea boots are everything right now and these two options show you some variety with this style of boot.

2) Nordstrom

Is there ever a list I make that does not feature Nordstrom? I have said it several times on this blog how much I appreciate their range of both clothing and shoes. When it comes to ankle boots, although their variety may be less than that of DSW, they still have some great options available.

Okay so one of my favorite ankle boots from Nordstrom does have a little bit of a heel but the heel height is minimal, don’t worry. These black ankle boots would look so great with a boot cut or wide leg jeans.

The pointed toe also makes it more elegant. The other pair of boots I’m loving from Nordstrom are these soft suede ankle boots by Ryder. The back zipper makes them easy to slip into while the minimal stacked heel makes them easy to walk in. I also love the dark brown color – perfect for fall.


If your budget for a new pair of flat ankle boots is on the lower end of the scale, then these next options are for you. ASOS is a great platform to search for trendy ankle boots however my issue is how quickly items sell out so by the time you’re reading this post, the shoes linked may be gone. If that is the case, feel free to let me know and I would do my best to find replacements just as good.

If you’re looking for ankle boots in a fun color, these khaki combat boots are a great option to spice your wardrobe up. I love the fact it has both a lace up and zipper detail. These boots right here are probably the best ankle boots to go with straight leg jeans and price tag is pretty great.

Now that I’ve shared my favorite spots to find cute and comfortable flat ankle boots, let us dive into the different outfits to be created with them. Also note that the same sites mentioned above sell great heeled ankle booties as well.

1) With a pair of skinny jeans

An easy way to create a classic look with flat ankle boots is to pair them with skinny jeans and a sweater. You could go with either blue or black skinny jeans and still be able to execute a great Fall look. If you shy away from bright colors, opt for sweaters in neutral colors to pair with your skinny jeans.

Get the look HERE

During the warmer weather, you could wear a tank top or white tee and add an open cardigan on top to create a nice and simple look to wear to a coffee shop or to the mall. Feel free to add a really long necklace as an accessory to bring the look up a notch.

Skinny jeans are my favorite types of jeans to wear with ankle boots because they’re so easy to tuck into the top of the ankle boots if necessary.

2) With leggings

I feel like this is a classic university student look because it’s so easy to put together while being stylish. You could wear an oversized sweater with a pair of black leggings and some black leather booties and no one would know you had pulled an all-nighter preparing for midterms. This is also such a warm look you could rock on a cold Fall day, adding a longline coat on top should you need it.

Get the look HERE

If you’re trying to look fancier either for date night or another special occasion, feel free to opt for ankle boots with high heels but this is not necessary. A nice shiny flat ankle boot would still do the trick.

3) With a midi dress

For an office-appropriate ankle boot look, opt for a sleeved dress in a neutral color add a pair of flat ankle boots and you’re ready to shine at the office. If it’s a little chilly outside, add a pair of leggings or black tights to your look to keep it classy yet warm. This same look could take you from office to after hours with a quick shoes change and some lip gloss.

Get the look HERE

If it’s nice outside, you could try wearing a strapless midi dress with a blouse underneath to give your dress a completely new look. If you worry about appearing shorter, make sure your ankle boots are really low and don’t cut you off around your calves.

4) With a mini skirt

A great way to style your ankle boots for bowling night or any casual gathering is by pairing them with a cute mini skirt. Make sure your skirt sits nicely at your waist for the most flattering look and you could also tuck your shirt, sweater, or blouse into it to really emphasize your waist. If you’re going to be doing some bending, wear a pair of tights to prevent any wardrobe malfunctions.

Get the look HERE

On a cold fall night, drape a black leather jacket across your shoulders to add some sass to your overall look and amp up the cool factor. Again, low ankle boots work better if you’re trying to appear taller. Just make sure to have fun with your choice of sweater or top and go for tops in bright colors if your boots are black or brown.

5) With maxi skirts

I feel like a broken record at this point given the number of times I talk about recycling your maxi skirts all year long. I can’t help it; maxi skirts are such a versatile piece of clothing and deserve to be styled as often as possible. With this wardrobe staple, you could add a sweater on top to create a functional yet stylish look for the colder weather. You could also wear a tank top and leather jacket with a maxi skirt in a solid color for another funky yet fashionable look.

Ankle boots are probably my favorite boots to wear with maxi skirts because all anyone really sees is the top of the boot. Knee boots are cute and all but they’re more of a hassle to wear (hello thick calves) and no one even gets to see their full beauty underneath all that skirt.

6) With Summer dresses

Summer dresses are a summer staple I encourage you to use as a transitional piece once temperatures start to drop. One of my favorite ways to do so is by wearing a thin sweater underneath my dress (or a short sleeved t-shirt) and then adding a leather jacket or denim jacket on top. My personal preferences of ankle boots to go with this outfit are a pair of black boots or white ones.

Image source here

This is just because a lot of my summer dresses come in bold and bright colors and prints and so a neutral boot color would prevent some serious color clashing. Summer dresses are also the best way to style cowboy boots. This is because cowboy boots are a more fun boot and with the flirty nature of summer dresses, make for a great laid-back look.

7) With pencil skirts

Headed back to office wear, flat ankle boots are the easiest way to style your everyday pencil skirt during the fall. This is great news to for those employees who take public transit to the office because you don’t have to worry about carrying an extra pair of shoes in your bag and slipping into those once you get to the office. You get to ride the bus and subway comfortably while staying warm and respecting office dress codes.

Get the look HERE

When it gets really cold, you could wear a pair of thermal leggings underneath your pencil skirt and still look every bit as stylish. When it’s time to impress your girls at happy hour, throw on a pair of boots with a stiletto heel and you’re good to go! If you have short legs and your pencil skirt hits you right at your knee, try to opt for really short boots. These would help to elongate your legs.

8) With wide-legged jeans

Ankle boots are THAT boot. They get to be paired with all types of jeans because they’re easy to be tucked into or to cover. Boot cut jeans for example work great with flat ankle boots, especially if they feature a pointed toe, because only the tip of the boots are displayed. Imagine trying to get thigh-high boots on underneath a boot-cut – whew! A pointed toe just gives this denim outfit a more polished look. You could add either a leather jacket or a nice long coat to complete this look.

9) With a cocktail dress

Little black dresses can be paired with flat ankle boots, ladies. We don’t need to be in heels every time we whip out the LBD. If you’re headed to an art gallery during the cooler months, consider pairing a black dress with either black or brown boots, a statement necklace and a longline cardigan for a chic artsy look. For a classic all-black look, a pair of black ankle booties would do the trick.

Image source here

Another way to style this look is by adding a white sweater on top of your LBD and making it look more a sweater and skirt combination. Yu could also swap the sweater for a white shirt during the warmer months to achieve the same look.

10) With pants/culottes

This look is probably a non-brainer but one that could easily be forgotten about. A white shirt paired with black pants or culottes still work in the fall and winter when paired with brown or black leather boots. You would be ready to face any director or co-worker in this polished look, perfect for the boardroom. You could also play around with shirts and blouses in different colors to figure out the right style for you, but the general rule is if your trousers are in a solid neutral color, any color top goes!

Get the look HERE

I hope you have gotten enough inspiration for both casual outfits as well as more dressy ways to style flat ankle boots. They don’t necessarily have to be saved for just your skinny jeans but can be styled so nicely with skirts and dresses.

You most likely already own most of the pieces mentioned in this blog post and so you may want to bookmark this to use as a sort of style guide the next time you pull out the flat ankle boots.

Regardless of your body type, there is a look on this you could totally rock this season, so what are you waiting for?

Until the next post,



If you're looking for some outfit inspo when it comes to wearing any Chelsea boot, check out my post: 13 Stylish Outfits to Wear With Chelsea Boots.

My blog post: The 15 Best Pants to Wear with Ankle Boots is a great guide on deciding the types of pants and jeans to pair with ankle boots.

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