It’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
Wide Leg Jeans with a Striped Turtleneck
Sweater (code: MAREE10) | Jeans | Boots | Bag (similar) | Sunglasses | Necklace (code: MAREE20)
Wide 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 Straight Leg Jeans
Straight Leg Jeans and a Chunky Turtleneck
Sweater | Jeans | Boots | Bag | Sunglasses
Straight leg jeans with a barn jacket
Jacket | Sweater (code: MAREE10) | Jeans (similar) | Boots | Bag (code: MAREESYE) | Belt (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
Cropped Jeans and a V-Neck Pullover
Sweater | Jeans | Boots (similar) | Bag (similar) | 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
Faux leather jeans and a bodysuit
Turtleneck | Jeans (similar) | Boots (similar) | Bag (similar) | Sunglasses
Monochromatic 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
Skinny 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
Distressed jeans with a quilted jacket and lug sole boots
Jacket (similar) | Turtleneck | Jeans | Boots | Sunglasses
Distressed jeans and a wool car coat
Coat (similar) | Turtleneck (similar) | Jeans | Boots | Bag (similar) | 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!
What Are Ankle Boots?
Ankle boots are typically defined as any boots that end near the ankle bone. That could be an inch or two above or even slightly below the actual ankle.
Types of Ankle Boots
Chelsea Boots
Chelsea boots are usually a flat boot that you can pull on easily. Typically they have elastic or a pull tab at the back to make them easier to get on without the need for zippers.
Pointy Toe Boots
As the name suggests, pointy toe ankle boots refer to the pointy shape of the toe. I find these to be the most elevated and timeless style of boots to own.
Lug Sole Boots
A lug sole boot is one with a thicker sole that is better equipped to walk in foul weather conditions.
Sock Boots
Sock boots are a fitted style of ankle boots that hug the foot and ankle tightly.
Kitten Heel Boots
Kitten heel ankle boots usually have a heel lower than 2 inches so it makes them much easier to stand in or walk for long period of time.
What Are the Most Comfortable Boots for Women?
The most comfortable boots are the ones that feel the best to you. Every person is different so it is a bit of trial and error determining what boots are the easiest to wear for long periods of time. If you do like a heeled boot, opt for a kitten heel style which still gives a bit of lift without being too high. I love chelsea boots for day to day life especially since there are dressier options available.
How Should Ankle Boots Fit?
It’s best to always get your ankle boots a tad big so you can wear socks or tights with them in the fall/winter.
Don’t forget to check out these sweaters you can add to your closet this winter to complete your look!
While I have always appreciated a comfy outfit from time to time, the older I get the more I am leaning into an entire comfy wardrobe. LOL I used to have a sweatshirt and maybe a pair of leggings to throw on when I didn’t feel like putting myself together, but that outfit has slowly morphed into an entire collection of clothing that is designed to be comfortable yet still looks super chic. I refuse to sacrifice style for comfort and definitely feel like you can successfully accomplish both in one look.
Outfit details: 
Outfit details: 
Outfit details: 
Outfit details: 
Outfit details: Sweater Coat (
Outfit details: 
Outfit details: Coat (
Outfit details: 
Comments