The best ways to style Flat Ankle Boots with Jeans for fall and winter

Are you looking for outfit inspiration on how to wear flat ankle boots with jeans? I’ve got you covered with the ultimate style guide of outfit ideas and different ways to make the most of this go-to combo.

We all have our favorite pair of ankle booties in our closet, along with our go-to pair of denim jeans.

How to Wear Flat Ankle Boots with Jeans (Styling Tips + Outfit Ideas)

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Whether it be skinny jeans that are very fitted to your leg and waist, mom jeans that have a baggier relaxed fit, straight-leg jeans, or flare jeans that don’t taper in towards your ankle, flat ankle boots are the perfect combination to pair with denim!

Ankle boots and jeans are such a classic combo that work for so many different occasions, no matter your personal preference for style!

As a petite woman, I tend to opt for shoes that have some sort of heel but since having kids, lately I have opted for more flat boot style as they are just more practical and comfortable for my day to day activities with my girls.

Whether you are looking for a casual look for mom duty, or a casual date night outfit I have got you covered with outfit inspiration and styling tips below.

Tips to Styling Flat Ankle Boots with Jeans:

#1 Height Matters 

Be mindful of this when choosing the shaft height of your flat boot. When it comes to wearing a flat boot, you are losing the flattering aspect that a heel brings to the leg.

A higher shaft boot works well for mom jeans, a lower shaft boot works best for skinny jeans.

#2 Choose the Right Jeans 

Choosing the right fitting denim is so important when styling flat ankle boots with jeans.

Finding jeans that hit you on the right spot on your ankle help to create an overall more streamlined, cleaner look when paired with flat ankle boots.

#3 Platform Height 

If you want the elongating effect of a heels but the comfort of a flat boot, opt for the platform style of flat boots or a wedge style!

This is great if you are on the petite side or just wanting to create a longer/leaner look to your leg. You would not believe how comfortable platform boots are.

#4 Match It Up

A great way to create a flattering look for ankle boots and denim is to opt for the same colored denim to match your boot (example: black skinny jeans and black pointed toe booties).

This is a great way to create a “dressier” or more put together look while still be ultra comfortable. I love to style outfits this way for date night!

#5 Cuff Your Jeans

A stylish detail to complete your look is so cuff your jeans to show off your cute flat ankle boots! This creates a flattering look to the leg and is also great if your jeans are a bit bulkier towards the ankle.

This is also a great way to custom fit your jeans length to your booties, as you can decide depending on the height of the boot with where you want your jeans to hit on your leg.

must have flat ankle boots

Different Types of Flat Ankle Boots:

  • Combat Boots
  • Chelsea Boots
  • Ugg Boots
  • Pointed Toe Boots
  • Winter Boots
  • Cowboy Boots

types of jeans to style with flat boots

must have types of jeans

Different Types of Jeans to wear with flat ankle boots:

  • Skinny Jeans
  • Mom Jeans
  • Straight-Leg Jeans or Straight Jeans
  • Distressed Jeans
  • Vintage Fit Jeans
  • Coated Jeans
  • Wide-Leg Jeans
  • Boyfriend Jeans
  • Black Jeans

Flat Ankle Boots and Jeans Outfit Ideas

I love warmer weather, but I also look forward to the colder months to pull out all of my boots, and putting together outfits with them. Here are some fun outfit ideas, along with tips and tricks to perfectly pairing ankle boots and jeans in an ultra-stylish way. Here are my expert tips and some current styles I absolutely love below!

How to Wear Flat Ankle Boots with Jeans

fall to winter outfit with flat boots

White Sweater + Black Straight Leg Jeans + Hiker Boots

A white sweater paired with jeans is the true definition of a classic look, especially in cooler weather.

I love the look of a crisp white seater with straight leg jeans, whether they are black like the ones shown above or blue with distressing, a white sweater is an easy item to pair with denim that always looks good and also works for a lot of different occasions.

Try to add in some fun texture or style with my accessories, so these Sherpa hiking boots were a fun flat ankle boot option to a casual winter outfit combo.

You can top this with your favorite coat or an oversized sweater, and bonus points for this outfit, since you can easily swap for heels to head out for drinks with friends.

Hiking boots like this pair very nicely with the straight leg style of jeans as they are bit chunkier and the straight fit around the ankle helps to balance it out.

You can also pair them with distressed mom jeans that are cuffed up for a cute cozy feel.

styling with different textures

White Tee Bodysuit + Shacket + Coated Skinny Jeans + Combat Boots

A great way to mix up your jeans and flat ankle boot combos is try different colors and textures.

I absolutely LOVE the look of coated denim, and these chocolate brown coated skinny jeans are so trendy right now.

They can easily be worn day to night and are so fun to style! I love them paired more casually with a suede Chelsea Boot, a cozy shacket and a basic bodysuit.

You could also pair these coated skinny jeans with pointed toe ankle boots and a blazer for a chic look.

Combat boots work very well with skinny jeans as they tuck in nicely to the taller shaft that combat boots typically have.

If you want to style mom jeans or straight leg jeans with combat boots, I suggest cuffing the jeans to fit at the top of the boot!

wear to work to happy hour

Black Skinny Jeans + Satin Cami + Blazer + Pointed Toe Anke Boots

Flat boots and jeans does not just have to be for casual settings! A great black pair of skinny jeans and faux leather pointed toe black boots is so flattering and looks so dressed up.

Pair these wardrobe staples with a fun colored satin cami and a blazer and you’re ready for dinner out or a work event!

This is a great outfit idea that would work very well for holiday parties as well.

Add some fun earrings or a crystal bag and you’re ready for cocktail hour while still being comfortable in your flat pair of ankle boots.

*Pro Tip* I love to style black skinny jeans with pointed toe black ankle boots for a really elongating look to my legs. This is such a flattering fit and is my go-to for date night when I just don’t feel like wearing heels.

casual and chic flat boots outfit idea

Skinny Jeans + Ugg Boots + Puffer Jacket

Ugg boots are really trending right now and they are such a comfortable option for a flat ankle boot.

You can really style them so many ways, but I especially love them paired with skinny jeans as they tuck in so nicely to the taller shaft height of Ugg boots that creates a really seamless look.

I love them paired with classic dark blue skinny jeans, a long sleeve turtleneck or bodysuit and a cute puffer jacket for winter.

This type of outfit will definitely be a go-to for me as we have snow and this is functional for winter weather while still being very stylish.

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