How To Wear Flat Ankle Boots With Jeans

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Jeans and boots are popular and extremely versatile items that many people already have in their wardrobe. But do you know how to wear flat ankle boots with jeans?

While both are quite simple to style, pairing them together to create a flattering look definitely requires some skill. With so many different styles of jeans and boots on the market today, you’ll need to choose the right style of each to create a seamless look.

I think it’s safe to say that at some point in your life, you’ve probably had a cute pair of ankle boots hidden in your closet that just never get worn because you couldn’t figure out what to wear them with. But, it doesn’t always have to be this way.

In this style guide, we’ll go over some simple tips to help you come up with different ways to easily put together chic outfits with jeans and flat ankle boots.

A woman crouched down showing how to wear flat ankle boots with jeans.

Flat Ankle Boots Styling Tips

In the fall and winter seasons, ankle boots and jeans are a perfect combination for many occasions. You can wear them while going grocery shopping, on a date night, or on casual Fridays at work. However, to pull this pairing off correctly, you will need to keep the following factors in mind.

Height of the Boots

When styling flat ankle boots with jeans, you must consider the shaft height of the boot. One downside of wearing flat boots is that they don’t provide the lengthening aspects of the legs as a boot with a block heel would. If you’re a petite woman, this might be a problem when trying to elongate the legs.

Depending on the type of jeans you wear, you may make yourself look shorter than you actually are. For example, lower shaft boots paired with skinny jeans can make you look taller.

When pairing lower shaft boots with skinny jeans you want to make sure the hem of your jeans doesn’t come down over the front of your boots. Leaving a small space between the jeans and boots helps to break up the look, thus creating a lengthening effect.

Alternatively, if you pair your jeans with a higher-shaft pair of boots, the high shaft height helps to draw the eyes up, which again results in a lengthening effect.

Opt for Platform Boots

Platform-style flat boots are an excellent option to get the taller effect of heels while enjoying the comfort of a flat boot. In addition to being great for petite individuals, it can also be used to create the illusion of longer legs.

Pay Attention to How the Jeans Look Around Your Ankle

Finding the perfect pair of jeans can be difficult as so many factors weigh in choosing the right style.

For example, you want them to fit perfectly around the waist and not create bulges while also fitting comfortably around your thighs. Finding a pair that fits perfectly in both regards while also being the perfect length is even harder.

There are a few retailers we love that offer jeans in a wide variety of fits for every body type including length, however, Abercrombie is our #1 recommendation.

Abercrombie offers jean styles in fits from dad to mom, curvy, skinny, etc., while also offering each in extra short, short, regular, long, and extra long – something you don’t see at most other retailers.

When it comes to pairing jeans with flat ankle boots you don’t want them to be too long as they may drag on the ground. Ideally, you want to pair flat ankle boots with jeans that hit just above your ankle as this helps to create a more sleek and polished appearance.

Consider Cuffing Your Jeans

If you want to show off your boots but your jeans are too long, your best option is to cuff your jeans. Cuffing jeans is a great way to customize the length of your jeans to your booties since you can decide which place on your leg your jeans will hit.

Match the Color of Your Jeans and Boots

Choosing the same-colored denim to match your boot is a great way to create a chic monochromatic look. For example, consider wearing black ankle booties with black skinny jeans. This creates a lengthening effect which works especially great for petites.

Using this method, you can create a “sophisticated” look while still remaining extremely comfortable. It’s a great outfit to wear when going out for a fun night and you want to dress up but not be overly dressed.

Of course, neutral colors always win when choosing this outfit; try not to go over the top by wearing bright colors. For example, matching yellow jeans with a pair of ankle boots may be a bit too much.

But, of course, everyone has their own personal style and taste. While not everyone will be willing to come out of their comfort zone quite this much, if you’re bold enough to do this, bonus points for letting your uniqueness shine.

Consider the Type of Boots and Jeans You Are Wearing

When thinking about boots you may only consider one type, but keep in mind there are many different options when it comes to flat ankle boots. 

Of course, the type of boot style you wear is a personal preference and you may prefer a certain type over the other. However, here are a few different types of ankle boots to choose from:

  • Ugg Boots
  • Chelsa Boots
  • Pointed Toe Boots
  • Cowboy Boots
  • Combat Boots

Although there are many styles to choose from, the style you wear will largely depend on the type of jeans you’re pairing them with. Before we discuss which combos go best, let’s go over a few different types of jeans that are often well-suited for flat ankle boots.

  • Straight Leg Jeans
  • Vintage Fit Jeans
  • Flare Jeans
  • Bootcut Jeans
  • Distressed Jeans
  • Skinny Jeans
  • Wide-Leg Jeans
  • Boyfriend Jeans

Now that you know some jeans and boot styles, let’s discuss some outfit ideas. Here are some of our favorite ways to style flat ankle boots no matter what style of jeans you choose.

How To Wear Flat Ankle Boots With Jeans

A women's outfit idea showing how to wear flat ankle boots with jeans and an oversized sweater.

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Ugg Boots & Skinny Jeans

The easiest way to wear Ugg boots is with ankle length skinny jeans. Why? Because skinny jeans easily tuck into boots. However, you shouldn’t limit yourself to just skinny jeans when wearing Ugg boots. You can wear boyfriend jeans and bootcut jeans with a pair of Ugg boots as well.

Ugg boots are the ultimate cozy shoe for the colder months. Throw on a cute oversized sweater or a button-front top with a bodysuit underneath for a cute but casual look.

A women's flat boots and jeans outfit idea.

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Black Skinny Jeans With a White Tee and Cardigan

Black jeans a great option for those days you really want to wear black leggings but want to look a little more put together. You can wear this outfit with just about any pair of flat ankle boots, such as Chelsea boots, Combat boots, or even Cowboy boots.

Women's denim on denim outfit with skinny jeans, a denim button up shirt, brown ankle boots, and a brown hobo bag

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Denim On Denim

Wearing an all denim outfit is not as popular as it was in the early 2000s, however, it’s a classic style that still looks nice when you’re out running errands or going to lunch with friends. It’s best to wear this outfit with neutral color boots to keep the outfit from clashing.

Women's all black outfit including black skinny jeans, gold hoop earrings, a gold layering necklace, a black blazer, a black satin cami, and flat black boots

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Blazer With Black Skinny Jeans and a Satin Cami

This look is great for date night and can even work for a casual Friday in the office. Even though black skinnies are casual, throwing on a blazer and a satin cami instantly adds a more sophisticated feel. Finish off this looks with drop earrings and a great top handle or crossbody bag.

When you wear a white or black top you have an almost endless selection of choices when it comes to the type of boots you can wear. Whether you opt for black booties or a pair of booties with a pop of color, you really can’t go wrong.

How to wear flat ankle boots with a puffer coat outfit idea.

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Puffer Jacket and Skinny Blue Jeans

Another casual but put-together look is a pair of skinny jeans paired with higher shaft boots and a puffer coat. A good rule of thumb when styling the two together is to opt for a shorter coat to create balance.

W women's outfit idea that shows how to wear flat ankle boots with jeans including a graphic tshirt, distressed jeans, and white ankle boots

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Distressed Jeans With A Graphic T-Shirt

Although we typically have warmer weather in summer, nighttime can still be chilly. For a summer night out pair your favorite distressed jeans and a graphic tee with white ankle boots. This looks is trendy and casual and a great way to look great while being comfortable while out with friends.

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Straight Leg Jeans and Sweater

Another classic look for the cold season is a pair of straight-leg denim jeans with a sweater. This outfit goes great with combat boots, winter boots, and pointed-toe boots. 

Just remember to pay attention to where the shaft of the boot falls. You either want your jeans to cover the top of the boots or leave a little space between them. You never want your jeans to sit on the tip of your boots.

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Boot Cut Jeans and Cowboy Boots

Cowboy boots look great with bootcut jeans. This look involves styling the jeans over the boots instead of under them.

It’s essential that jeans fit accurately around the waist and upper legs but have a wider leg opening to fit over the top of the boot comfortably. Finish the look with your favorite blouse to go to create a casual yet chic look.

Women's outfit idea showing how to wear flat ankle boots with jeans including a black moto jacket, a white blouse, and combat boots

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Black Leather Jacket, White Top, and Combat Boots

You can never go wrong with a classic black-and-white combo, especially during the fall and winter months. A leather jacket takes a simple white sweater, denim jeans, and black leather boots outfit from classy to baddie in no time. Gold hoop earrings are the perfect finishing touch.

an outfit idea showing how to wear flat ankle boots with jeans and a striped sweater including brown boots, a brown purse, and gold earrings.

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White jeans, neutral sweater, brown ankle boots

White jeans are great for transitioning from one season to the next so it’s always a great idea to keep at least one pair in your closet. In spring they pair beautifully with floral tops and wedges but in the fall season, they look great with a pair of brown ankle boots or riding boots and a neutral-colored sweater.

Conclusion

No matter what boot style or color palette you prefer, there are so many different outfits you can put together with jeans and flat ankle boots. What matters most is that you’re comfortable and feel confident in your outfit.

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