50 Booties Outfits For This Fall: Autumn Looks With Ankle Boots

By Kaia Saunders / Updated on November 15, 2018
Give your summery boho dress a fall makeover by pairing it with comfy brown booties

Fall is here! Time to transform your summer wardrobe and bring out fall essentials like fluffy cardigans, wooly scarves, warm jumpers, and cute booties!

They are perfect shoes for the fall considering the “just-right” temperatures and their versatility. Plus, you can wear booties comfortably for hours and they always look adorable!

Wearing Booties With Rolled Up Jeans

Rolled up jeans are a great way to show off your pretty booties. You can either buy cuffed jeans or roll up your existing ones for a casual fall look that you can wear anywhere. Just remember to leave a little gap between the cuff and your boots. Letting your ankle peek out will visually elongate your legs. Longer legs FTW!

You can’t go wrong with a blue jumper on blue jeans and brown booties. Add a colorful scarf to break the monotony.Photo: asliceofstyle.com

You can’t go wrong with a blue jumper on blue jeans and brown booties. Add a colourful scarf to break the monotony.

A blanket scarf will never go out of style and it’s a great way to add some drama to your fall look.Photo: glitterchampagne.com

A blanket scarf will never go out of style and it’s a great way to add some drama to your fall look.

Plain black booties don’t have to be boring. Wear a jumper with chunky stripes and add a chunky necklace to look like a true fashionista.Photo: yuboots.com

Plain black booties don’t have to be boring. Wear a jumper with chunky stripes and add a chunky necklace to look like a true fashionista.

Boyfriend jeans look super chic with suede grey booties.Photo: pinterest.com

Boyfriend jeans look super chic with suede grey booties.

For a classic fall look, pair your rolled up jeans with booties and a slouchy, oversized cardigan.Photo: prettydesigns.com

For a classic fall look, pair your rolled up jeans with booties and a slouchy, oversized cardigan.



Dress It Up: Your Ankle Boots With A Dress

Just because summer has bid adieu doesn’t mean you have to do the same to your dresses. It’s all about styling them with a fall twist. Think jackets, layers, leggings, and of course booties! Here are some of our favorite ways to wear dresses during fall.

Give your summery boho dress a fall makeover by pairing it with a blazer and comfy brown bootiesPhoto: stylishwife.com

Give your summery boho dress a fall makeover by pairing it with a blazer and comfy brown booties.

Wearing a dress with leggings and booties is an oldie but goodie. Plush velvet ankle boots will add a sophisticated touch to this lookPhoto: fashiontasty.com

Wearing a dress with leggings and booties is an oldie but goodie. Plush velvet ankle boots will add a sophisticated touch to this look.

A monochromatic outfit is always a fashion win, especially when fierce booties are part of the lookPhoto: pinterest.com

A monochromatic outfit is always a fashion win, especially when fierce booties are part of the look.

Sweatshirt dresses with booties are absolutely perfect for fall! Add a 90s element to your look by tying a sweater around your waistPhoto: Instagram/@cmcoving

Sweatshirt dresses with booties are absolutely perfect for fall! Add a 90s element to your look by tying a sweater around your waist.

An all-black look is always sexy, especially if it’s date nightPhoto: wheretoget.it

An all-black look is always sexy, especially if it’s date night!

Looks With Flirty Skirts

Just like dresses, you don’t have to give up on skirts just yet. It’s all about longer lengths, layers, and booties to keep your feet warm. Check out some of our favorite outfit ideas with skirts for fall.

A midi skirt is apt for cooler fall temperatures. Throw on a long cardigan and your trusty brown suede booties for a well put together look that is ideal for work.Photo: pinterest.com

A midi skirt is apt for cooler fall temperatures. Throw on a long cardigan and your trusty brown suede booties for a well put together look that is ideal for work.



This look screams fashionista! Everything from that luscious violet skirt to the belted jacket to the chic black boots is just pure perfection.Photo: pinterest.com

This look screams fashionista! As if it is an elegant french fashion icon from the streets in Paris. Everything from that luscious violet skirt to the belted jacket to the chic black boots is just pure perfection.

Print on print can be intimidating but what is fashion without a little adventure? Pair your tribal print skirt with a polka dotted jumper. Complete the look with neutral booties.Photo: petitejoysinlife.wordpress.com

Print on print can be intimidating but what is fashion without a little adventure? Pair your tribal print skirt with a polka dotted jumper. Complete the look with neutral booties.

Layers are to fall what pen is to paper. Wear a denim shirt with a striped skirt and throw on a grey sweater and brown booties for a flawless fall look.Photo: pinterest.com

Layers are to fall what pen is to paper. Wear a denim shirt with a striped skirt and throw on a grey sweater and brown booties for a flawless fall look.

A short skirt is just as adorable during fall as it is during summer. Pair your grey mini with a striped top, black cropped sweater, and black booties. Add a little colour with a checkered scarf.Photo: pinterest.com

A short skirt is just as adorable during fall as it is during summer. Pair your grey mini with a striped top, black cropped sweater, and black booties. Add a little colour with a checkered scarf.

Tucked In Your Boots

Tuck your pants into your booties for a classic look that has been around for as long as we can remember! This look is best attempted with skinny jeans and pants but you can also achieve the same by cuffing and putting socks over slightly broader pants before tucking them in.

For a statement office look, try tucking your skinny black pants into grey studded boots. Wear this with an emerald green top and a tan blazer and you’re ready to win the “Best Dressed Employee” of the month award.Photo: pinterest.com

For a statement office look, try tucking your skinny black pants into grey studded boots. Wear this with an emerald green top and a tan blazer and you’re ready to win the “Best Dressed Employee” of the month award.

Lazy but want to look like you’ve made an effort? Try this simple but chic look with a white top, black distressed jeans, tan booties, and a trusty denim jacket.Photo: pinterest.com

Lazy but want to look like you’ve made an effort? Try this simple but chic look with a white top, black distressed jeans, tan booties, and a trusty denim jacket.

Turn on the sexy in a deep V neck top with skinny pants tucked into brown booties. This is a fashiontastic look for brunch with the girls!Photo: Instagram/@emilyanngemma

Turn on the sexy in a deep V neck top with skinny pants tucked into brown booties. This is a fashiontastic look for brunch with the girls!



Leather moto jackets are eternally sexy. Wear yours with a simple tee and skinny jeans tucked into a pair of badass booties.Photo: quemsabegosto.wordpress.com

Leather moto jackets are eternally sexy. Wear yours with a simple tee and skinny jeans tucked into a pair of badass booties.

For a sweet, girly look pair a cowl neck top in this season’s hottest colour- millennium pink with your trusty blue jeans and some sassy booties.Photo: pinterest.com

For a sweet, girly look pair a cowl neck top in this season’s hottest colour- millennium pink with your trusty blue jeans and some sassy booties.

Make a Statement

Why fit in when you can stand out in statement booties?

While regular booties in black, brown, and grey are absolute fall essentials, we also highly recommend splurging in a pair of statement ankle boots that will make heads turn!

These stunning golden booties are really something else! Metallics are huge this season but if you aren’t sure about going all out, this is a great way to subtly incorporate the trend into your look. Keep the rest of your outfit simple so that your boots can shine bright!Photo: pinterest.com

These stunning golden booties are really something else! Metallics are huge this season but if you aren’t sure about going all out, this is a great way to subtly incorporate the trend into your look. Keep the rest of your outfit simple so that your boots can shine bright!

If golden boots aren’t really your thing, try something more understated but sexy like these oxblood beauties.Photo: wheretoget.it

If golden boots aren’t really your thing, try something more understated but sexy like these oxblood beauties.

If you’re a girl who loves her blacks and browns, try out a pair of booties with an interesting pattern.Photo: wheretoget.it

If you’re a girl who loves her blacks and browns, try out a pair of booties with an interesting pattern.

Animal prints can quickly go from sexy to tacky if not worn right. Thankfully, that’s something you don’t have to worry about with animal print booties.Photo: pinterest.com

Animal prints can quickly go from sexy to tacky if not worn right. Thankfully, that’s something you don’t have to worry about with animal print booties. Keep the rest of your look simple and add a statement bag to complement your booties.

Florals for fall? Yes, please!Photo: adaisychaindream.com

Florals for fall? Yes, please!



Impressive black skirt matched with black bootsPhoto: lookbook.nu

Impressive black skirt matched with black boots. Isn’t this a cute look for a day date?

De-stress with Distressed

Love ‘em or hate ‘em, but you just can’t ignore ‘em. Distressed and ripped jeans continue to rule the roost when it comes to the fashion world.

They are fabulous for fall and add a real rockstar quality to your look. So, how should you wear them this year? Check out these stylish examples.

Save yourself the trouble of folding and cuffing by investing in a pair of ankle length distressed jeans. A leather jacket really changes an otherwise simple look for the better.Photo: prettydesigns.com

Save yourself the trouble of folding and cuffing by investing in a pair of ankle length distressed jeans. A leather jacket really changes an otherwise simple look for the better. Tie a checkered shirt around your waist to add a 90s inspired touch to this trendy look.

A white top with blue jeans is a classic combination that you can’t go wrong with. Add a twist by wearing a sweater top with exaggerated sleeves and let your jeans sit casually on top of your booties.Photo: Instagram/@miamiamine

A white top with blue jeans is a classic combination that you can’t go wrong with. Add a twist by wearing a sweater top with exaggerated sleeves and let your jeans sit casually on top of your booties.

Balance out excessively ripped jeans by pairing them with a long jacket and a high-necked top. Add a beanie for good measure and you’re ready to rock this beautiful season!Photo: closetfulofclothes.com

Balance out excessively ripped jeans by pairing them with a long jacket and a high-necked top. Add a beanie for good measure and you’re ready to rock this beautiful season!

A knotted shirt with ripped jeans is always a good look, no matter what the seasonPhoto: Instagram/@cmcoving

A knotted shirt with ripped jeans is always a good look, no matter what the season. Take a break from blue jeans and try something in military green instead. Top it off with velvet open toe booties for a fashion forward look.

Voluminous sleeves add a feminine touch to any outfit, especially when it’s in pink. Pair it with ripped jeans and statement perforated booties.Photo: Instagram/@hoboken_in_heels

Voluminous sleeves add a feminine touch to any outfit, especially when it’s in pink. Pair it with ripped jeans and statement perforated booties. Excellent!



Say Yes to Leggings

Leggings and booties are a winning fall combination.

Not only are they insanely comfortable, but they also just work together flawlessly. Check out these outfits that will make you say “Yes, please”.

Keep it simple and sophisticated in plain black leggings, an oversized blanket scarf, and chunky booties. Add a hat for that extra chic factor.Photo: styleoholic.com

Keep it simple and sophisticated in plain black leggings, an oversized blanket scarf, and chunky booties. Add a hat for that extra chic factor.

Just because this combination has been around forever, doesn’t mean it has to be boring. Wear a pair of cool leggings with studded booties and a wide brimmed hat.Photo: pinterest.com

Just because this combination has been around forever, doesn’t mean it has to be boring. Wear a pair of cool leggings with studded booties and a wide brimmed hat.

Stay stylish all day long in this all-black look. Play with texture by adding a leather jacket over your jumper and get ready to slay!Photo: outfitideashq.com

Stay stylish all day long in this all-black look. Play with texture by adding a leather jacket over your jumper and get ready to slay!

An oversized sweater with your leggings is without a doubt one of the best fall combinations. Add a twist (no pun intended) by rolling up your leggings and showing off your ankles and booties.Photo: becomechic.com

An oversized sweater with your leggings is without a doubt one of the best fall combinations. Add a twist (no pun intended) by rolling up your leggings and showing off your ankles and booties.

If you really want to push yourself, why not try some fierce leather leggings and chained booties? What a showstopper!Photo: kenzas.se

If you really want to push yourself, why not try some fierce leather leggings and chained booties? What a showstopper!

Maxi-mum Comfort

Is there anything more comfortable than maxi dresses and skirts? We think not! The maxi trend is here to stay, so why not make the best of it during fall?

A bright mustard yellow maxi skirt with booties is the perfect way to add some color to a dull day. Don’t forget a chic leather jacket to make the look fall worthy.Photo: aelida.com

A bright mustard yellow maxi skirt with booties is the perfect way to add some color to a dull day. Don’t forget a chic leather jacket to make the look fall worthy.

Photo: wheretoget.it

Transform a flowy white dress from a summer look to a fall one by throwing on a black fringe jacket and black booties.



Be it summer, winter, or fall, slits are always sexy!Photo: wheretoget.it

Be it summer, winter, or fall, slits are always sexy!

Try a printed skirt with a basic white tee, beige cardigan, and fringed booties for a fun fall look.Photo: styleoholic.com

Try a printed skirt with a basic white tee, beige cardigan, and fringed booties for a fun fall look.

A knit maxi skirt with golden booties is a bold but fabulous choice!Photo: wheretoget.it

A knit maxi skirt with golden booties is a bold but fabulous choice!

Shorty Shorts (And Booties, Of Course)

Shorts may be the last thing you think of wearing during fall but trust us when we say you don’t have to throw them at the back of your closet just yet. Don’t believe us? Check out these cute ways to flaunt your shorts during fall.

Pair your simple black shorts with black stockings, a grey tee, booties, and a colored jacket.Photo: lookbook.nu

Pair your simple black shorts with black stockings, a grey tee, booties, and a colored jacket.

Try a heavy knit sweater with distressed shorts and studded booties for an effortlessly chic fall look.Photo: pinterest.com

Try a heavy knit sweater with distressed shorts and studded booties for an effortlessly chic fall look.

For warmer fall days, keep it simple but sexy in classic daisy dukes and a white tee. Add a bomber jacket and black booties et voila!Photo: wheretoget.it

For warmer fall days, keep it simple but sexy in classic daisy dukes and a white tee. Add a bomber jacket and black booties et voila!



Take your “crop top and shorts” look from summer to fall by throwing on a suede fringed jacket and blue velvet booties.Photo: whowhatwear.com

Take your “crop top and shorts” look from summer to fall by throwing on a suede fringed jacket and blue velvet booties.

Stay Warm in Outerwear

As the temperatures continue to drop, you will of course need to bring out your jackets and coats. But just because you’re all “covered up” doesn’t mean that you can’t look runway ready. Check out these chic outfit ideas.

This monochromatic black and grey look with a long coat and a knit scarf is super chic!Photo: justthedesign.com

This monochromatic black and grey look with a long coat and a knit scarf is super chic!

Fall and layers go hand in hand. Pair your ripped jeans with a checkered top, a sweater, a long coat and your trusty black booties.Photo: justthedesign.com

Fall and layers go hand in hand. Pair your ripped jeans with a checkered top, a sweater, a long coat and your trusty black booties.

If an all-black look is too boring for you, bring it to life with a beautiful statement yellow jacket. Add white booties for an interesting touch.Photo: justthedesign.com

If an all-black look is too boring for you, bring it to life with a beautiful statement yellow jacket. Add white booties for an interesting touch.

Channel your inner biker girl by trying a black on black look with a military green sweatshirt and an oxblood biker jacket. So fierce!Photo: justthedesign.com

Channel your inner biker girl by trying a black on black look with a military green sweatshirt and an oxblood biker jacket. So fierce!

Want to add a luxe touch to your fall outfit? Why not try a velvet coat and beautiful animal print booties?Photo: justthedesign.com

Want to add a luxe touch to your fall outfit? Why not try a velvet coat and beautiful animal print booties?

Excited to rock your booties this fall? We sure are!


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