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How to wear booties with skirts, dresses and pants!

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

As the temperature continues to drib, we accept these booties beyond jeans and leggings pairings (although you'll find those here besides) and venture into skirt and dress territory as well.

Yes, it is like shooting fish in a barrel to rely on onetime faithful styling and not run the risk of creating a disproportionate await with the wrong dress-booties combination.

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

Full general "rules" for wearing booties

At that place are never any hard and fast "rules" in fashion, but below are a few factors you might desire to think about when choosing your talocrural joint boots.

Call back about where your booties terminate

Booties can be super flattering. However, they tin also create the opposite event. If you have long, slender legs, you lot're lucky – you lot tin wear your booties any way you desire to.

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

However, if you lot aren't so confident near your legs and desire to create a slimming event, y'all will want to consider the shaft acme of your booties. Brand sure your booties end at the slimmest part of your legs or your ankles. Otherwise, you will stop up cartoon attending to the widest role 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, pocketbook, earrings and sunglasses.

For an elongating event: 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 every bit your jeans, leggings or tights can be a nifty fashion to do then.

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

Check out this printed dress that you tin habiliment with this similar pair of booties, moto jacket, tights and crossbody pocketbook.

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 tin can still habiliment your summertime skirts and dresses or your cropped jeans. Merely team with booties and a cardigan or calorie-free 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 like 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 practice get with everything. Read on for the most flattering way to wear them with your leggings, jeans, pants, dresses and skirts.

Yous can article of clothing for work, for evening events or dinner out, or more casually. Below you lot'll notice plenty of options to adjust your lifestyle.

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

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

Women's ankle boots: The all-time booties styles to choose this season

Before looking further at what to article of clothing with your ankle booties, and how to wear them, let'due south accept a wait at some of the different styles of talocrural joint boots you could cull.

While there may but be subtle differences between many, there are countless styles y'all could opt for. Beneath 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 mode, with its elasticated side console went on to exist popularized by everyone from The Beatles to The Rolling Stones, so at that place's no danger of the Chelsea boot existence off trend.

Wonders D-8707 Chelsea boot | 40plusstyle.com

Wonders 'D-8707' Chelsea boot

Rubberband insert booties

For another accept on the Chelsea kicking, you could opt for a pointed toe, cake heel version like these Linea Paolo boots (beneath) 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 blackness booties (below) adds a modern take on a archetype style.

Miz Mooz 'Ashton' bootie | 40plusstyle.com

Miz Mooz 'Ashton' bootie

Lace-upward booties

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

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

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 sparse, stiletto heels, and so a block heel could be the way to become. The booties past Lucky Make (below) come either in this dark grey shade, archetype blackness or a light tan.

Lucky Brand 'Walba' bootie | 40plusstyle.com

Lucky Make '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 archetype leather style. Suede, or a suede-look bootie, tin 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 apartment or accept a wider, block heel, if you want to add a more formal element to your outfit, you could cull a slim kitten heel.

Kitten heel booties would work well if you're heading out for dinner or you have an issue to attend. They also wait great when work with piece of work outfits.

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

CC Corso Como 'Darshina' bootie

On-trend booties

Texture was a fundamental element of the wintertime and fall 2022 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 atmospheric condition isn't also cold where you are, you lot could bear witness 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. Merely make certain 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 Greenish 'Cayanne' leather peep toe sandal

Black zip up booties

Rather than opt for a pull on way, you could choose a pair of zip upwardly booties. I can't remember of annihilation these Lucky Brand zip up boots (below) wouldn't get with.

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

Lucky Brand 'Basel' ankle bootie

Cowboy fashion booties

A pair of tan or biscuit booties tin be a good selection 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 (beneath) 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 summertime shoes, particularly espadrilles. Merely, yous can likewise add a wedge to your booties to add some extra summit.

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

Dr. Scholl's 'Noelle' bootie

What to wear with booties

Now, that you've called your favorite pair of booties, allow'south take a expect at what you might desire to vesture with them.

Booties with leggings

Wearing your booties with leggings is a classic pairing that is perfect equally 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 expect 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-upwards boots.

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

How to wear booties with leggings | 40plusstyle.com

Outfit 1: Eileen Fisher silk crepe bateau neck shell – Everyday Ritual long cardigan – Zella high waist leggings – CC Corso Como 'Darshina' bootie – rag & bone shopper tote – Etsy beaded necklace

Outfit 2: Eileen Fisher ballet neck tunic – Ellen Tracy plaid belted glaze – Lyssé denim leggings – BC 'Anything Is Possible' vegan leather bootie – Madewell leather tote – Karine Sultan pendant necklace

Outfit iii: COS leather top – Lauren Ralph Lauren blazer glaze – SPANX faux leather leggings – Wonders 'D-8707' Chelsea boot – Kurt Geiger leather tote – Karine 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 mayhap the easiest style choice. Still, there are some guidelines to follow so y'all don't create a disproportionate and unflattering silhouette.

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

Monochromatic looks (blueish 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 elevation of the boot. Jeans (or fifty-fifty trousers depending on the occasion) tin be styled with a cuff to add a more coincidental chic look.

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

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

Booties and pants outfit ideas | 40plusstyle.com

Outfit 1: Vince cashmere sweater – French Connexion moto jacket – Madewell crop pull-on pants – Miz Mooz 'Ashton' bootie – Nordstrom wrap scarf

Outfit 2: Samsøe Samsøe wrap blouse – Via Spiga hooded trench coat – FRAME crop mini boot jeans – Paul Green 'Cayanne' leather peep toe sandal – Madewell leopard tote – Karine Sultan pendant necklace

Outfit three: Eileen Fisher tee – Leith long cardigan – AG ingather jeans – Sole Guild 'Lolanna' pointed toe bootie – Tory Burch leather crossbody handbag – Jenny Bird layered necklace

How to clothing talocrural joint 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 brim the taller the boot".  Of course, this rule can be broken depending on styling and torso shape. Longer skirts can get away with shorter booties.

 You can besides promote a more lean await by keeping the lesser monochromatic. Showing more than of the ankle besides 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 aforementioned color for an elongating expect.

Bank 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 pullover – Love, Burn print midi brim – Sole Lodge 'Faunya' block heel boot – Tory Burch leather crossbody bag – Dean Davidson earrings

Outfit two: Topshop crop funnel neck sweater – Loveappella scroll peak maxi skirt – Linea Paolo 'Vu' Chelsea bootie – Tory Burch leather crossbody pocketbook – Karine Sultan pendant necklace

Outfit 3: maje sweater – Ming Wang bank check knit brim – Lucky Make 'Basel' ankle bootie – Madewell 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 tin can sometimes be a catchy endeavor. The key here is to once again pay attention to getting your proportions right and promoting a long wait that does not visually chop your body in half. An easy style tip is to go for a monochromatic await that creates a lean look.

Booties are curt enough to not shorten your leg (especially when paired with a shorter dress and leggings). Yous could also wear with longer dresses and leave a little leg on brandish, or wear with tights for colder atmospheric condition.

You could choose brusque dresses with boots and squad with tights or leggings or article of clothing a longer dress with your ankle boots.

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

Complete her await with this similar bucket purse, earrings and sunglasses.

Booties and dresses outfit ideas | 40plusstyle.com

Outfit one: AWARE by VERO MODA dress mock neck midi clothes – BLANKNYC suede moto jacket – DailyShoes western cowboy bootie – rag & bone shopper tote – Kate Spade New York stud earrings – Halogen rib cashmere scarf

Outfit two: COS belted leather wearing apparel – Nordstrom Signature turtleneck pullover – Lucky Brand 'Walba' bootie – Tory Burch leather crossbody bag – Dean Davidson earrings

Outfit three: Chelsea28 shirred minidress – Zella loftier waist leggings – Wonders 'D-8707' Chelsea boot – rag & bone shopper tote – Etsy beaded necklace

Beneath y'all volition observe some of the looks shown above together in one booties sheathing for winter and fall to give you more inspiration on what to wear ankle boots with.

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

How to wear talocrural joint boots: A capsule wardrobe

Booties capsule wardrobe | 40plusstyle.com

How accept you been wearing your booties this season? I'd love to hear your ain tips on how to clothing booties.

Continue reading:

  1. The Best Wintertime Boots For Women: Stylish Winter Boots That You lot Tin't Wait To Wear
  2. Best Shoes With Curvation Support – Comfy Walking Shoes To Walk In All Twenty-four hours!
  3. The Best Wide Calf Boots For Winter And Fall

Like this post on how to vesture booties? Share it on Pinterest!

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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