7 Ways to Wear Flat Ankle Boots With Jeans and Pants

You can tell by now that I’m really big on ankle boots with jeans – it seems I just keep blogging about this look. I blame it on the fact that I have very thick calves and thighs and so most of my boots end up having to be ankle-length since nothing else can fit.

You may have your reasons as to why you love this look but as Fall is quickly approaching, I thought I could come back and give you some more style tips on how to rock this look.

This time, I would be sharing ways to rock flat ankle boots (because sometimes we don’t want the extra inches in height) with not only straight-leg jeans but also other styles of jeans including mom jeans, boot cut, boyfriend jeans, cropped, flared jeans and more.

Ankle boots are already considered wardrobe essentials if you live in a country where temperatures drop significantly, so why not make the most of them?

To start off, I’ll repeat myself and say when it comes to styling a pair of ankle boots, jeans which can be tucked into the boot without bunching up are the best option. Or, if you don’t mind hiding most of your boot away, a flared boot works as well.

The style of boot you end up going with would depend on the look you are going for – casual or more dressed up.

As all of these boots would be flat, to achieve a more dressed up look would rely heavily on the finishing of the boot as well as the rest of your outfit.

Here are my favorite ways to to style flat boots with jeans:

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

5 Ways to Wear Flat Ankle boots With Jeans

1) Flat ankle boots + skinny jeans

It goes without saying that this is the easiest way to style your flat boots. They’re super easy to tuck in while keeping everything smooth around your ankles. Whether your jeans are black, blue or any other color, pairing them with a pair of solid color ankle boots always works great.

Remember to think of complimentary colors if you’re avoiding a monochromatic look.

Get similar ankle boots HERE

For example, neutrals all work well together (black, white, brown, grey) and if you’re playing it safe, you can work just around those. However, if your outfit is already a neutral color, you can play around with a more bold choice in boot color such as burgundy, red, green or even animal print.

If there is going to be a lot of walking in your outfit, or you are a commuter, chelsea boots and black ankle boots would both be great options.

For a more casual look, try on some combat boots with a denim jacket. In the Fall season and Winter months, consider going with a darker wash denim and some brown ankle boots.

Re-create this look HERE

2) Flat ankle boots + wide-leg jeans

If skinny or straight leg jeans are not your style of jeans, you can definitely rock the ankle boots + denim look, just slightly differently. A pointed toe flat boot is a great option to go with when the top of your boot is covered by the hem of your jeans.

That pointed toe elongates the legs and also adds dimension to what is a flatter look compared to a tucked in skinny jean.

As we are not going with a heeled boot for the purpose of this post, wearing a top that cuts off right at your waist, or which can be tucked in, would also help to elongate your torso.

I Love these wide leg jeans by Good American.

Consider a crop top or sweater or even a tank top which you’ve tucked in – this really flatters the waist when wearing a pair of flare jeans.

For outerwear, I would suggest a moto jacket, shorter puffer jacket, trench coat or Longline blazer. Pointed black booties and cowboy boots are both great choices of flat boots to go with.

3) Flat ankle boots + Cropped jeans

A cropped pair of jeans is my second best choice of denim jeans to go with ankle length boots. This is because they don’t even need any tucking and so keep the lines smooth and clean around the ankles.

They also get to have your boots on full display, meaning you get to play around more with boot styles. A lot of mom jeans and boyfriend jeans can be rolled up at the cuffs once or twice to give you that cropped look.

Remember, this works if the jeans are straight-legged as a wide-legged jean would tend to unroll itself if folded up. However, if you’re determined to make this look work with your wide-leg jeans, then some pins can be used to keep your jeans up.

A great way to complete this look is with a white top or sweater and a flannel shirt or jacket for a seamless look.

Get similar boots HERE

4) Flat ankle boots + bootcut jeans

Similar to the wide leg jeans are the bootcut jeans in that these jeans cover the top part or even most of your ankle booties. These are the perfect jeans to pair with ankle boots in bright colors. With your entire leg being covered up, a pop of color would be unexpected and refreshing at the same time.

If you’re going for a colored ankle boot, keep the rest of your outfit pretty complimentary so as to avoid clashing. Unless color clashing is your thing of course, then by all means!

I love this shade of red ankle booties!

When it comes to picking a jacket to go with bootcut jeans, my personal preference is to go with a shorter coat or jacket in a solid color.

This is such a classic style and reminds me of something Cindy Crawford would have worn back in the day. The best ankle boots to go with this outfit would be ones with an almond toe or pointed toe.

4) Flat ankle boots Flat ankle boots + distressed jeans

The ultimate casual look right here. There are so many different ways to pull off the distressed denim + ankle boot look and my favorite is probably pairing some distressed black jeans with a graphic tee and a black leather jacket.

Your jeans could be cropped, regular length or even wider and it would still be a great outfit combo.

Doc Martens are the best ankle boots to achieve this look with.

For a sexy look you can wear for date night, consider wearing a low cut bodysuit with your distressed black skinnies and low ankle boots – you’ll be both sexy and comfortable.

Another perfect combination, perhaps for the Fall would be distressed jeans with an oversized sweater and a hat. This look would also work well if you swap your ankle boots for some tall boots and if the jeans are not flared.

5) Flat ankle boots + leggings

We are now moving into styling ankle boots with other common items most people already have in their closets. First on the list is a pair of black leggings. This is such an easy way to style flat boots or any boots for that matter because a wide range of tops or sweaters could be used.

Consider a sweater dress for a night out, an oversized sweater for a casual outing or to stay at home, and a shift dress if you’re headed to the office and want a polished look.

A lot of people worry that ankle boots may cut them off and make them appear shorter but not if the bottoms are monochromatic or if the boots are low cut.

Leggings are also thin enough to not need any folding before being tucked into the boots- giving you a sleeker look.

6) Flat ankle boots + a pencil skirt

Another item most women already own is a pencil skirt. During the cooler weather, black tights or leggings could be worn underneath your pencil skirt and button-up shirt for some extra warmth and a full winter coat draped across your shoulders.

If it’s warmer outside, consider wearing a mini skirt and black top with your pair of boots for some cute chic look.

If you’ve never tried it before, white ankle boots are such a good look to go with a skater dress, a midi skirt or a sweater dress.

Betsey Johnson has some of the prettiest white ankle boots I’ve seen!

7) Flat ankle boots + maxi skirt or dress

I don’t know why but this look just reminds me of a Texas music video. Ankle boots can be worn with many maxi skirt and dresses mostly because your feet are barely visible underneath.

This would be the best time to go for an open-toe bootie as it could add some more fun to your outfit and make it more interesting.

If height is your concern, you can definitely get away with a heeled ankle boot. You’ll look so much taller not only because of the heels but also thanks to the long skirt or dress.

I have an entire post dedicated to footwear that goes with maxi dresses and long skirts.

As usual, I hope I have provided you with some great outfit ideas you can use the next time you pull out those cute ankle boots but are unsure how to style them. The best way to know what style you like most is to try them all.

I can only give you so many ideas but your personal style would dictate which route you decide to choose.

You might want to check out the links I provided in this post because they’re some of the best boots for each outfit I’ve described.

Let me know if you have any questions, I’m happy to help.

For some more outfit inspiration when it comes to pairing jeans with ankle boots, check out my post: 5+ Ways to Wear Ankle Boots With Straight Leg Jeans.

Until the next post,