How to Wear Ankle Boots with JeansIt’s officially boot season and I could not be more excited! I have more pairs of boots in my closet than I care to admit so I wear them all season long to get my money’s worth. LOL Especially when it gets cold, wearing flats with my jeans won’t cut it. I have a mix of boot styles in my closet – both knee high boots and ankle boots but tend to reach for ankle boots more when I’m wearing jeans. A simple classic pair of ankle boots with go with just about any pair of  jeans. For me a pointy toe, high heel ankle boot in either black or brown is a staple for me and something I wear year after year. It never goes out of style. In today’s post, I’m sharing how to style ankle boots with various different denim and hopefully give you some outfit ideas to recreate.

How to Wear Ankle Boots with Jeans

How to Wear Ankle Boots with Wide Leg Jeans

How to Wear Ankle Boots with Wide Leg JeansWide Leg Jeans with a Striped Turtleneck

Sweater (code: MAREE10) | Jeans | Boots | Bag | Sunglasses | Necklace (code: MAREE20)

Wide Leg Jeans with a Printed TopWide Leg Jeans with a Printed Top

Cardigan | Shirt | Jeans | Boots | Bag

Wide Leg Jeans with a CardiganWide Leg Jeans with a Cardigan

Cardigan (similar) | Jeans | Boots | Bag | Sunglasses

Wide Leg Jeans with a Tweed JacketWide Leg Jeans with a Tweed Jacket

Jacket (similar) | Turtleneck | Jeans | Boots (similar) | Bag | Sunglasses

When wearing wide leg jeans with ankle boots, it’s best to choose an ankle bootie with some height. This allows the wide leg jean to drape and skim the floor without bunching up or dragging on the ground. Either a pointy heel or a block heel would work – it just depends on your preference. This is one of the only style of jeans that may work with knee high boots if you want because there is more room for them to fit under the jeans. For more ideas of how to style wide leg jeans, here is a post with a ton of different suggestions.

How to Wear Ankle Boots with Slit Hem Jeans

How to Wear Ankle Boots with Slit Hem JeansSlit hem jeans with a rollneck sweater

Sweater | Jeans | Boots | Bag | Sunglasses

Much like styling wide leg jeans, wearing a slit hem jeans works best when you choose a high heel. My preference is always a pointy toe because it helps to elongate the legs.

How to Wear Ankle Boots with Straight Leg Jeans

How to Wear Ankle Boots with Straight Leg JeansStraight Leg Jeans and a Chunky Turtleneck

Sweater | Jeans | Boots | Bag | Sunglasses

Straight leg jeans and a bodysuitStraight leg jeans and a bodysuit

Shirt (similar) | Jeans | Boots (similar)

Straight leg jeans and a button down shirtStraight leg jeans and a button down shirt

Coat (similar) | Shirt (similar) | Jeans | Boots (similar) | Bag

Straight leg jeans with a shacketStraight leg jeans with a shacket

Shirt jacket (similar) | Jeans | Boots | Bag (similar) | Sunglasses

Straight leg jeans are a great alternative to a skinny jean style because they are a slight step up in terms of looseness. Be sure when wearing ankle boots with straight leg jeans that they go under the jean and there is no bit of leg or gap showing. This will create a longer line and balance out the look. If you are wearing black jeans, try a black pair of ankle boots which will really help to elongate the look and create a seamless line from the waist to the floor.

How to Wear Ankle Boots with Cropped Jeans

How to Wear Ankle Boots with Cropped JeansCropped Jeans and a V-Neck Pullover

Sweater | Jeans | Boots (similar) | Bag (similar) | Sunglasses

Cropped Jeans and a Long Sleeve TeeCropped Jeans and a Long Sleeve Tee

Shirt | Jeans (similar) | Boots (similar)

Cropped Jeans and a cropped cardiganCropped Jeans and a cropped cardigan

Cardigan (similar) | Jeans (similar) | Boots | Bag | Sunglasses

Similar idea with cropped jeans (or jeans that are ankle length) as straight leg jeans, be sure the top of the jeans still cover or meet the top of the boot. Also choose a slim style ankle boot or even a sock bootie so it balances out the proportion of the cropped jean. If you want a boot without any height, you can always opt for flat chelsea boots which would work too.

How to Wear Ankle Boots with Faux Leather Jeans

How to Wear Ankle Boots with Faux Leather JeansFaux leather jeans and a tweed jacket

Jacket (similar) | Turtleneck | Jeans (similar) | Boots (similar) | Bag (similar)

Faux leather jeans and a bodysuitFaux leather jeans and a bodysuit

Turtleneck | Jeans (similar) | Boots (similar) | Bag (similar) | Sunglasses

Monochromatic look with faux leather jeansMonochromatic look with faux leather jeans

Sweater (similar) | Jeans (similar) | Boots (similar) | Scarf (similar) | Bag (similar) | Sunglasses

I love wearing faux leather jeans in the fall and winter and my favorite way to style them is with simple black ankle boots. Either suede or leather is fine because both will look great with faux leather. I have them styled with a high heels ankle boot, but a simple flat classic ankle boot would work well.

How to Wear Ankle Boots with Skinny Jeans

How to Wear Ankle Boots with Skinny JeansSkinny jeans and a plaid shacket

Shacket (similar) | Turtleneck | Jeans | Boots | Bag (similar) | Sunglasses

Skinny jeans and a fair isle sweaterSkinny jeans and a fair isle sweater

Sweater (similar) | Jeans | Boots (similar) | Bag (similar) | Sunglasses

I still have a few pairs of skinny jeans in my closet but I definitely style them differently now with ankle boots than I used to. I prefer the ankle boot to go under the jeans instead of over them. It looks more modern and doesn’t cut off my leg in a weird way. If you want to wear skinny jeans, choose a sock bootie or something very slim around the ankle to easily fit under and not look too bulky. Also make sure the hem of your jeans cover the top of your boot and doesn’t leave a gap.

How to Wear Ankle Boots with Distressed Jeans

How to Wear Ankle Boots with Distressed JeansDistressed jeans with a quilted jacket and lug sole boots

Jacket (similar) | Turtleneck | Jeans | Boots | Sunglasses

Distressed jeans and a wool car coatDistressed jeans and a wool car coat

Coat (similar) | Turtleneck (similar) | Jeans | Boots | Bag | Sunglasses

I showed two different ways to style distressed jeans with ankle boots. You can definitely dress them up a bit with a sleek pointy toe ankle bootie or choose something more casual like a lug sole boot. As with most of the other denim styles, I recommend having the jeans fall over the top of the boot instead of tucking them in. It looks more modern and elongating.

Though most of the denim I shared in this post are blue, black or dark denim, I still love wearing white jeans in the fall and winter. All my styling tips would apply to those too. If you need ideas of what to wear with white jeans, I have an entire blog post dedicated to it!