Booties are key for a well-edited closet. More versatile than their knee high sisters, booties will take you through all four seasons.  You’ll find plenty of ideas on how to wear booties below with chic ankle boots outfit inspiration and some of the best women’s ankle boots in stores now.

As the temperature continues to drop, we take these booties beyond jeans and leggings pairings (although you’ll find those here too) and venture into skirt and dress territory as well.

Yes, it is easy to rely on old faithful styling and not run the risk of creating a disproportionate look with the wrong dress-booties combination.

However, we’ve got you covered with 12 looks covering pants, skirts, and dresses as well as style inspiration from 40+ readers.  The key is to make sure your ankle boots style flatters your legs and lends a lean and chic look to your ensemble.

General “rules” for wearing booties

There are never any hard and fast “rules” in fashion, but below are a few factors you might want to think about when choosing your ankle boots.

Think about where your booties end

Booties can be super flattering. However, they can also create the opposite effect. If you have long, slender legs, you’re lucky – you can wear your booties any way you want to.

How to wear booties - Nadine wears leopard print booties with a long cardigan | 40plusstyle.com

However, if you aren’t so confident about your legs and want to create a slimming effect, you will want to consider the shaft height of your booties. Make sure your booties end at the slimmest part of your legs or your ankles. Otherwise, you will end up drawing attention to the widest part of your calves.

Nadine (above) wears a stylish pair of leopard print booties which end at her ankles.

Recreate her outfit with these similar leopard print booties, shirtdress, cardigan, bag, earrings and sunglasses.

For an elongating effect: Black booties outfit

How to wear booties - Melissa wears booties with tights and a dress | 40plusstyle.com

If you want to create the illusion of longer legs, then wearing a pair of booties in the same color as your jeans, leggings or tights can be a great way to do so.

Melissa (above) shows how you can still wear your summer dresses for winter and fall by adding tights, booties and a moto jacket.

Check out this printed dress that you can wear with this similar pair of booties, moto jacket, tights and crossbody bag.

They’re the perfect transitional footwear

How to wear booties - Abi wears booties with cropped jeans | 40plusstyle.com

When the weather starts to cool, you can still wear your summer skirts and dresses or your cropped jeans. Just team with booties and a cardigan or light jacket rather than the sandals you wore during the warmer months.

Abi (above) wears her cropped jeans with booties, and leaves a little ankle showing.

Steal her look with this similar pair of booties, top, coat, jeans, crossbody bag, necklace, earrings and sunglasses.

You can wear them anywhere and with anything

How to wear booties - Jona wears booties with white jeans | 40plusstyle.com

Booties really do go with everything. Read on for the most flattering way to wear them with your leggings, jeans, pants, dresses and skirts.

You can wear for work, for evening events or dinner out, or more casually. Below you’ll find plenty of options to suit your lifestyle.

Jona (above) opts to bring her white jeans from summer to fall by wearing with booties and a poncho.

Check out these similar leather booties, shirt, cardigan, jeans and necklace.

Women’s ankle boots: The best booties styles to choose this season

Before looking further at what to wear with your ankle booties, and how to wear them, let’s take a look at some of the different styles of ankle boots you could choose.

While there may only be subtle differences between many, there are countless styles you could opt for. Below are some of my favorites in stores now:

Chelsea boots

With their roots in Victorian times, Queen Victoria was said to wear a version of Chelsea boots everyday. The style, with its elasticated side panel went on to be popularized by everyone from The Beatles to The Rolling Stones, so there’s no danger of the Chelsea boot being off trend.

Wonders D-8707 Chelsea boot | 40plusstyle.com

Wonders ‘D-8707’ Chelsea boot

Elastic insert booties

For another take on the Chelsea boot, you could opt for a pointed toe, block heel version like these Linea Paolo boots (below) which have a wavy elastic insert.

Linea Paolo 'Vu' Chelsea bootie | 40plusstyle.com

Linea Paolo ‘Vu’ Chelsea bootie

Ruched booties

Ruching can be very flattering when it comes to your clothes, and ruched boots or shoes are particularly on trend this season.

The ruching at the front of these Miz Mooz black booties (below) adds a modern take on a classic style.

Miz Mooz 'Ashton' bootie | 40plusstyle.com

Miz Mooz ‘Ashton’ bootie

Lace-up booties

Lace-up booties have never been out-of-style as such, but they are definitely having a fashion moment for 2020, largely because styles from the 1990s are now back on trend.

You could opt for delicate, ladylike, Victorian style lace-ups, or chunkier boots such as the lace-up style below by Sole Society.

Sole Society 'Faunya' block heel boot | 40plusstyle.com

Sole Society ‘Faunya’ block heel boot

Block heel booties

If you like to add a bit of height, but you prefer not to walk on thin, stiletto heels, then a block heel could be the way to go. The booties by Lucky Brand (below) come either in this dark gray shade, classic black or a light tan.

Lucky Brand 'Walba' bootie | 40plusstyle.com

Lucky Brand ‘Walba’ bootie

Pointed toe boots

These booties below from Sole Society have an on-trend slouch at the back.

Sole Society 'Maeryn' pointed toe bootie | 40plusstyle.com

Sole Society ‘Maeryn’ pointed toe bootie

Suede booties

You don’t have to opt for a classic leather style. Suede, or a suede-look bootie, can be the perfect option as the weather starts to cool down before winter really arrives.

The burgundy booties (below) would add a pop of autumnal color to your fall outfits.

BC 'Anything Is Possible' vegan leather bootie | 40plusstyle.com

BC ‘Anything Is Possible’ vegan leather bootie

Kitten heel booties

While many ankle booties are flat or have a wider, block heel, if you want to add a more formal element to your outfit, you could choose a slim kitten heel.

Kitten heel booties would work well if you’re heading out for dinner or you have an event to attend. They also look great when work with work outfits.

CC Corso Como 'Darshina' bootie | 40plusstyle.com

CC Corso Como ‘Darshina’ bootie

On-trend booties

Texture was a key element of the winter and fall 2020 shoe trends. In particular, reptilian textures featured heavily on the catwalks.

Sole Society 'Lolanna' pointed toe bootie | 40plusstyle.com

Sole Society ‘Lolanna’ pointed toe bootie

Peep-toe booties

If the weather isn’t too cold where you are, you could show off your manicure and add a touch of modernity to your outfit with a pair of peep-toe booties.

Don’t worry, when it gets really chilly, you can wear them with tights. Just make sure that your tights look relatively new, with no pilling on the toes, and that the toe seams aren’t too obvious.

Paul Green 'Cayanne' leather peep toe sandal | 40plusstyle.com

Paul Green ‘Cayanne’ leather peep toe sandal

Black zip up booties

Rather than opt for a pull on style, you could choose a pair of zip up booties. I can’t think of anything these Lucky Brand zip up boots (below) wouldn’t go with.

Lucky Brand 'Basel' ankle bootie | 40plusstyle.com

Lucky Brand ‘Basel’ ankle bootie

Cowboy style booties

A pair of tan or beige booties can be a good option for transitional weather if you prefer a softer color rather than a dark shade such as black for your booties.

These cutout booties from Amazon (below) have a slight cowboy (or girl) feel to them and come in a choice of colors.

DailyShoes western cowboy bootie | 40plusstyle.com

DailyShoes western cowboy bootie

Wedge booties

Wedges are a popular style for summer shoes, particularly espadrilles. But, you can also add a wedge to your booties to add some extra height.

Dr. Scholl's 'Noelle' bootie | 40plusstyle.com

Dr. Scholl’s ‘Noelle’ bootie

What to wear with booties

Now, that you’ve chosen your favorite pair of booties, let’s take a look at what you might want to wear with them.

Booties with leggings

Wearing your booties with leggings is a classic pairing that is perfect as the weather cools down.

You could either choose to wear your leggings and booties with a long tunic top or with a dress. Take a look how to wear leggings for more inspiration.

How to wear booties - Lou wears lace-up booties with leggings | 40plusstyle.com

Lou (above) wears her coated leggings with an oversized shirt and lace-up boots.

Recreate her outfit with this similar pair of boots, shirt, jacket, leggings and earrings.

How to wear booties with leggings | 40plusstyle.com

Outfit 1: Eileen Fisher silk crepe bateau neck shellEveryday Ritual long cardiganZella high waist leggingsCC Corso Como ‘Darshina’ bootierag & bone shopper toteEtsy beaded necklace

Outfit 2: Eileen Fisher ballet neck tunicEllen Tracy plaid belted coatLyssé denim leggingsBC ‘Anything Is Possible’ vegan leather bootieMadewell leather toteKarine Sultan pendant necklace

Outfit 3: COS leather topLauren Ralph Lauren blazer coatSPANX faux leather leggingsWonders ‘D-8707’ Chelsea bootKurt Geiger leather toteKarine Sultan pendant necklace

Ankle boots with jeans and pants

How to wear booties - Armida wears booties with turned up pants | 40plusstyle.com

Booties with jeans or trousers are quite possibly the easiest style choice. However, there are some guidelines to follow so you don’t create a disproportionate and unflattering silhouette.

The key is to select booties that can carry a tune on their own and don’t mind being the star of the show (because they will definitely be on display).

Monochromatic looks (blue booties with blue jeans or black booties with black trousers) also create a longer and more flattering look. Select a slim or straight leg that hovers right above the top of the boot. Jeans (or even trousers depending on the occasion) can be styled with a cuff to add a more casual chic look.

Armida (above) cuffs her pants to show off a little bit of ankle above her red booties.

Get her look with these similar red booties, sweater, jeans, crossbody bag, necklace and earrings.

Booties and pants outfit ideas | 40plusstyle.com

Outfit 1: Vince cashmere sweaterFrench Connection moto jacketMadewell crop pull-on pantsMiz Mooz ‘Ashton’ bootieNordstrom wrap scarf

Outfit 2: Samsøe Samsøe wrap blouseVia Spiga hooded trench coatFRAME crop mini boot jeansPaul Green ‘Cayanne’ leather peep toe sandalMadewell leopard toteKarine Sultan pendant necklace

Outfit 3: Eileen Fisher teeLeith long cardiganAG crop jeansSole Society ‘Lolanna’ pointed toe bootieTory Burch leather crossbody bagJenny Bird layered necklace

How to wear ankle boots with skirts

How to wear booties - Karen wears booties with a maxi skirt | 40plusstyle.com

The general rule regarding skirts with booties is “the shorter the skirt the taller the boot”.  Of course, this rule can be broken depending on styling and body shape. Longer skirts can get away with shorter booties.

 You can also promote a more lean look by keeping the bottom monochromatic. Showing more of the ankle also allows you to get away with a shorter boot, as does a heel to elongate the legs.

Karen (above) keeps her booties and tights the same color for an elongating look.

Check out these similar suede booties, sweater, cardigan, midi skirt and sunglasses.

How to wear booties with skirts | 40plusstyle.com

Outfit 1: Nordstrom Signature turtleneck pulloverLove, Fire print midi skirtSole Society ‘Faunya’ block heel bootTory Burch leather crossbody bagDean Davidson earrings

Outfit 2: Topshop crop funnel neck sweaterLoveappella roll top maxi skirtLinea Paolo ‘Vu’ Chelsea bootieTory Burch leather crossbody bagKarine Sultan pendant necklace

Outfit 3: maje sweaterMing Wang check knit skirtLucky Brand ‘Basel’ ankle bootieMadewell leather tote

Dresses with ankle boots

How to wear booties with skirts, dresses and pants - we show you 12 chic ankle boots outfit ideas | 40plusstyle.com

Like skirts, pairing booties with dresses can sometimes be a tricky endeavor. The key here is to once again pay attention to getting your proportions right and promoting a long look that does not visually chop your body in half. An easy style tip is to go for a monochromatic look that creates a lean look.

Booties are short enough to not shorten your leg (especially when paired with a shorter dress and leggings). You could also wear with longer dresses and leave a little leg on display, or wear with tights for colder weather.

You could choose short dresses with boots and team with tights or leggings or wear a longer dress with your ankle boots.

Jill (above) is wearing a long dress with boots. Her dress is from Target and styles it with a Gucci belt and a pair of booties from Cole Haan.

Complete her look with this similar bucket bag, earrings and sunglasses.

Booties and dresses outfit ideas | 40plusstyle.com

Outfit 1: AWARE by VERO MODA dress mock neck midi dressBLANKNYC suede moto jacketDailyShoes western cowboy bootierag & bone shopper toteKate Spade New York stud earringsHalogen rib cashmere scarf

Outfit 2: COS belted leather dressNordstrom Signature turtleneck pulloverLucky Brand ‘Walba’ bootieTory Burch leather crossbody bagDean Davidson earrings

Outfit 3: Chelsea28 shirred minidressZella high waist leggingsWonders ‘D-8707’ Chelsea bootrag & bone shopper toteEtsy beaded necklace

Below you will find some of the looks shown above together in one booties capsule for winter and fall to give you more inspiration on what to wear ankle boots with.

You could swap many of these clothes and accessories around to create different looks as well as adding tights or leggings to any of the looks with dresses and skirts to add extra warmth for winter.

How to wear ankle boots: A capsule wardrobe

Booties capsule wardrobe | 40plusstyle.com

How have you been wearing your booties this season? I’d love to hear your own tips on how to wear booties.

Continue reading:

  1. The Best Winter Boots For Women: Stylish Winter Boots That You Can’t Wait To Wear
  2. Best Shoes With Arch Support – Comfortable Walking Shoes To Walk In All Day!
  3. The Best Wide Calf Boots For Winter And Fall

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How to wear booties with skirts, dresses and pants - we show you 12 chic ankle boots outfit ideas | 40plusstyle.com

Feature image by Jill

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