Last Updated on November 15, 2023 by Eve Dawes
The ankle boots outfits we’re wearing from Fall through Spring
Ankle boots outfit ideas to get the most wear out of yours whether you’re looking for a casual ankle boots outfit, something more work appropriate or glam for a night out. Ankle boots are that boot that sometimes just gets stuck as a boots and jeans outfits. As a fashion stylist, I often get asked how to change things up. So yes, I’m sharing how to wear ankle boots with jeans but there’s also so many more ways to wear and style them I wanted to share with you. Whether your style’s more classic or you’re looking for a more fashion forward way to wear flat or heel iterations this year. I have tons of stylish ideas for black ankle boots outfits, white, metallic or whatever else you have in your closet that’s dying to see the light of day (or grey sky) more.
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25 ways to style ankle boots
These ankle boots outfit ideas will help you get the most wear from all of the ankle boots in your closet or on your wishlist. Whether you’re looking for more ways to style your ankle boots with jeans or something fresh, keep scrolling. If you’re looking for knee high boot outfit ideas, I have lots of those in another article too.
1. How to style ankle boots with a leather mini dress
A leather mini dress, styled with or without tights adds an edgy, cool girl aesthetic to your ankle boots outfit and works with pretty much any color combination. I’m styling mine with a cozy faux fur coat this season to soften up the look and add a luxe touch.
2. Fall ankle boots outfit idea | With a sweater dress and bare legs
This is probably the way I style them the most often in Autumn to be fair. As it works both for Fall and Spring. For Winter I just add tights or leggings.
3. With a sweater dress and tights
As above but with the addition of sheer, opaque or logo tights for an extra layer of warmth. Have fun playing with prints and colors to change up your look.
4. Cozy casual ankle boots outfit idea | Sweater dress + leggings
A casual, comfortable and warm way to wear your flat or heeled ankle boots. I tend to wear either chunky lug sole or heeled ankle boots with my leggings to work with my petite proportions and cheat some extra height.
5. How to wear ankle boots with jeans | Classic style
Ankle boots and jeans and a camisole, bodysuit, t-shirt or sweater are a classic ankle boots outfit idea that’s easy to style casually with flats or dress up with heeled ankle boots, gold jewelry and a red lip.
Ankle boots outfit ideas jeans styling tip: Skinny jeans can be styled over or tucked into ankle boots but straight or wider leg jeans looks best styled over them. Which is how I’ve been tending to wear them this year.
6. How to wear ankle boots with jeans | Elevated casual style
Dress up a simple white or black t-shirt and jeans with a chic blazer and heeled boots for a relaxed but elevated ankle boots outfit idea.
I’ve worn my black ankle boots both under and over my black skinny jeans. I tend to find the jeans sit better when pulled over the boots. As they get a bit crinkled when tucked in but it’s nice to have options. Whereas my wider leg jeans I always style over them.
7. What to wear with ankle boots to work
For an ankle boots outfit idea that’s suitable for the office, swap your jeans and t-shirt for pants and a button down down shirt or camisole, or even a 3 piece suit for an instantly work appropriate look.
8. How to wear ankle boots with jeans and more denim!
Styling ankle boots with denim and more denim can be tricky but also look amazing. So think about proportions when considering how to wear ankle boots with jeans and other denim items.
Double denim is still trending and this outfit works by mixing and matching any or all of the following in the same color wash: jeans, jean shorts, denim skirt, denim jacket and denim ankle boots.
Just watch proportions and how you accessorize so it looks more fashion and less like an extra from a Western movie.
9. How to wear ankle boots with denim jeans shorts
Denim jean shorts and a tank or tee is a classic casual ankle boots outfit for everyday that will never go out of style. It doesn’t matter whether it’s a plain, graphic or logo tee for this look. It also works equally well with chunky lug sole ankle boots as it does with heeled ankle boots.
The style of boots or booties you go and what you layer over your top for will dramatically change the overall aesthetic. Don’t be afraid of the juxtaposition of stiletto heels and denim shorts. It’s an easy way to elongate your legs. Just be careful with the fit and styling to keep it in classy territory. As it can quickly go wrong!
10. Cute ankle boots outfit idea for Summer | Summer mini dress and ankle boots
A floaty, white, black or even colorful summer mini dress works with pretty much all style of ankle boots from western cowboy boots to platform or flat boots. For a more feminine look stick to streamlined heels, for an edgier look go for chunky lug sole boots.
I tend to stick to the same color palette e.g. a white dress with white ankle boots but have fun playing with monochromatic looks and mixing colors.
11. Take it to the max with a maxi dress
A summer maxi dress or maxi sweater dress both work well with ankle boots. For extra warmth layer tights underneath too. To draw more attention to your boots, go for a hemline that hits just above the top of your boots or a split hem like the one I’m wearing below.
For more of a statement style, accessorize with your favorite hat or belt to add more shape and draw attention to your waistline.
12. How to wear ankle boots with black jeans
An easy and flattering black ankle boots outfit idea is to style black slim-leg jeans or even plain black leggings with heeled black ankle boots and a black roll neck sweater to create a sleek monochromatic black ankle boots outfit. If you’re opting for leggings, go for a longer line top to keep the look less athletic and more stylish.
A monochromatic look is one of the best ways to create an elongated look that’s also slimming for a warm Winter black ankle boots outfit. Monochromatic looks also work with any color but black tends to be the most flattering.
13. Transitional season ankle boots outfit idea
Swap your roll neck sweater to a black bodysuit or cami with a blazer to go with your black jeans for Fall or Spring.
It also looks more elevated than a lot of other ankle boots outfits. Especially when styled with a gold button double breasted blazer, gold hoop earrings and winged eyeliner.
14. Sexy ankle boots outfit
A leather skirt or leather shorts and sheer or logo tights is a way sexier way to wear your ankle boots than with leggings. Style it with a corset or silk cami for a night out or more glam day time look or with a bodysuit or t-shirt for a more relaxed but sexy look.
15. Trending ankle boots outfit
Slouch socks aren’t going anywhere and add a retro look to flat ankle boots. Channel your inner Lady Diana and style them with leggings and a graphic sweater for a comfortable, casual ankle boots outfit.
16. Elevated ankle boots and leggings outfit for all seasons
Heeled ankle boots, with leggings, a t-shirt and blazer make for an elevated casual ankle boots outfit. For a warmer Fall Winter ankle boots outfit, swap your blazer for a cozy jacket.
This white and tan leather one comes in lots more colors and is super warm and cozy.
17. Edgy but feminine Summer style
Chunky sole ankle boots and a summery dress make for a feminine but edgy outfit. It doesn’t matter whether it’s a solid color or print, wear whatever you feel best in.
18. Midi skirt and ankle boots outfit idea
A midi skirt and roll neck sweater is ideal for Fall/Winter. Go for a printed skirt like tartan which is a huge trend this Winter for a high impact look. For an equally on trend but sexier look, try a leather midi skirt instead.
19. Combat style
Combat booties with a floaty dress or maxi skirt give an edgy look to an otherwise feminine, romantic style.
20. How to wear ankle boots with jean shorts | Western style
Western style cowboy ankle boots and jeans, jean shorts or a denim skirt will always be a classic outfit combo.
21. Glam outfit idea
Stiletto heel ankle boots, tights, shorts and a roll neck sweater mean you can keep your legs out longer during the cooler temperatures. If your style’s a little edgier, swap the stilettos for flat combat boots or a chunkier sole.
22. Coordinated chic
Match textures for a cohesive look whether that’s a tulle mini dress with tulle ankle boots, denim on denim or leather on leather.
23. Casual ankle boots outfit that’s not jeans
Loungewear isn’t just for sneakers, try styling your loungewear with your ankle boots instead for a less athletic and more stylish look.
24. Casual street style | Bike shorts and ankle boots
Ankle boots worn with bike shorts and a bomber or oversized jacket is a great way to show some leg in a casual way for Spring or Fall.
25. Chic black ankle boots outfit
Style your blazer dress with ankle boots for a look that works for both the day and night. A tailored blazer dress looks great for work or a satin or velvet style gives a luxe touch for the evening.
Your ankle boots outfits don’t just to have be monochromatic, white or black ankle boot outfits. Jewel tones and animal print boots make for an unexpected, statement making combo.
Do you wear skinny jeans in or out of ankle boots?
Skinny jeans should normally be worn inside your ankle boots otherwise the ankle boots can bulge out from underneath but play around and see what works best for you. The same goes for knee or thigh high boots. Besides leggings and tights, they’re really the only denim style that goes inside of your boots.
Pretty much all other styles of denim from boot cut to boot slit to straight or wide leg jeans should be worn outside of your boots or booties.
If you have a statement pair or ankle boots, skinny leg, boot slit, cuffed or cropped jeans that hit above the boots is a great way to show them off.
Is it OK to wear ankle boots with a dress?
Everyone agrees from RealSimple to the stylists at StitchFix that yes it’s absolutely ok to wear ankle boots with a dress. It’s one the most classic ways to style ankle boots. Whether that’s with a summer mini dress, maxi dress or sweater dress. It’s an outfit combo that works for all seasons. So throw on your favorite dress and booties and go.
More boots to complete your outfit with and more outfit ideas we’re loving right now
From the best ankle boots to style these outfits with to other boots on my wishlist. Here’s what’s hot and what’s not:
For more style, fashion and outfit ideas. As well as sale alerts and discount codes.