How to wear booties with skirts, dresses and pants – we show you 12 chic ways

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.

While it’s easy to pair booties with your pants or jeans, it can be harder to wear them with your skirts or dresses. That’s why this article concentrates on booties with dress outfit ideas.

As the temperature continues to drop, we take these booties beyond jeans and leggings pairings and venture into skirt and dress territory.

Yes, it is easy to rely on old faithful styling because you don’t want to run the risk of creating a disproportionate look with the wrong dress-booties combination.

However, we’ve got you covered with looks covering 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 or edgy look to your ensemble.

General guidelines on how to wear 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.

They’re the perfect transitional footwear

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.

Kylie @kylish_aus above wears a dress that would easily work for spring and summer. She makes it cold weather appropriate by teaming with booties and a fur jacket. Note she coordinates the color of her shoes and coat.

Recreate her outfit with this similar dress (another option here), jacket (another option here) and booties.

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.

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.

You can wear them anywhere and with anything

Booties really do go with everything. Read on for the most flattering way to wear them with your 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.

Nancy @nancysstyle above (read her style interview here) wears her booties with a maxi dress.

Check out these printed dresses from Maggy London, ba&sh and Karen Millen that you can wear with this similar pair of booties, necklace and sunglasses.

short boots with dresses For an elongating effect

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

Match the style of your boots to the style of your dress

If you are wearing a formal dress, you could wear with elegant kitten heel booties, or you could wear lug sole boots with a more casual dress.

Wear with tights

If you aren’t sure how to wear your booties with dresses, wearing with opaque tights is easy and stylish.

Women’s ankle boots: how to wear booties with dresses 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 if you’re looking at boots to wear with dresses ideas:

leather boots

A pair of black leather boots is an absolute classic. You could wear with casual maxi dresses, and add a moto jacket for warmth.

COS Leather Chelsea Boots

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. A paler shade can give your outfit a softer look.

Geox Bigliana Pointed Toe Bootie

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. The Steve Madden boots (below) are particularly on trend because of their chunky, lug soles.

Steve Madden Hayle Platform Chelsea 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 Franco Sarto booties (below) come in a good choice of neutrals, and are well reviewed. Wearers say they are flattering for wide calves, and go well with skirts.

Franco Sarto Stevie 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 with work outfits.

Sam Edelman Ulissa Booties

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.

Cordani Genesis Peep Toe Bootie

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. They’d be good to wear with your summer dresses so you can wear them into the cooler months.

LifeStride Dynasty Booties

Suzie @suzie.richetti above shows how you can wear booties with your dress for evening out.

Get her look with this similar dress (another option here), moto jacket, booties and necklace.

On-trend booties

Color and sculptural shapes were key elements of the winter and fall 2022 shoe trends. Adding an on-trend pair of booties can update your dresses outfits. You could try the t-shaped heel of the Tory Burch booties (below).

Tory Burch T Block Heel Ankle Bootie

Or, you could try the glamorous option of the gold heel booties (below).

Franco Sarto Tiera Bootie

waterproof boot

If it’s rainy or snowy where you are, you’ll need a pair of waterproof booties to keep you dry. The waterproof Chelsea boots (below) will give a contemporary look to your dresses.

Dolce Vita Hawk H20 Waterproof Chelsea Boot

lug sole bootIE

If you want to add a little edge to your outfits, you could try adding stud detailing to your boots.

Nine West Junga 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 skirt and sweater outfit

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.

& Other Stories Mock Neck Sweater – Keasmto Silk Satin Skirt – Sam Edelman Ulissa Booties – Tory Burch Kira Chevron Convertible Shoulder Bag – LA MENO Perfect Set Hoop Earrings

Karen @styledbykaren above shows how you can mix styles from different seasons to create a stylish outfit.

Steal her look with this similar cardigan, (another option here), maxi skirt, booties and sunglases.

Booties with dresses for winter and fall: sweater dress with boots

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 it with longer dresses and leave a little leg on display, or wear it with tights for colder weather. Below is a style you could try that mixes neutrals.

Karen Millen Italian Virgin Wool Maxi Oversized Coat – Chelsea28 Wrap Sweater Dress – Nine West Junga Bootie –Tory Burch Kira Chevron Convertible Shoulder Bag – Karine Sultan Cultured Peacock Pearl Drop Earrings

evening dress with boots

You can create a glamorous, slightly unexpected look by pairing your evening dress with booties. Look out for kitten heels styles or peep toe boots.

Karen Millen Crop Knit Cardigan – Karen Millen Crepe Waterfall High Neck Midi Dress – Cordani Genesis Peep Toe Bootie – HOBO Mila Leather Clutch – Karine Sultan Cultured Peacock Pearl Drop Earrings

Booties with casual dresses and skirt

Booties look fabulous with casual or shorter dresses teamed with leggings.

ATM Anthony Thomas Melillo Print Ripstop Shirtdress – Dolce Vita Hawk H20 Waterproof Chelsea Boot – Zella Live In High Waist Leggings – Ted Baker London Equesa Equestrian Bucklet Leather Bucket Bag – LA MENO Perfect Set Hoop Earrings

Kimba @kimbalikes gets her winter dress ready by wearing booties, layering a sweater underneath, and a cardigan over the top.

Check out this printed dress (another option here) that you can wear with this similar cardigan (another option here), pants and booties.

shorter dress and boots outfit

You could choose short dresses with boots and team them with tights or leggings. For an evening-ready option, you could wear heeled booties and leather-look leggings.

Ted Baker London Piara Ruffle Asymmetric Minidress – FRAME Leather Leggings – Tory Burch T Block Heel Ankle Bootie – Ted Baker London Equesa Equestrian Bucklet Leather Bucket Bag – LA MENO Perfect Set Hoop Earrings

ankle boots with dress: Midi dress option

You can wear your booties with any hem length. Wear with midi dresses and leave a little skin showing, or opt for tights if it’s chilly.

COS Printed Midi Shirtdress – Steve Madden Hayle Platform Chelsea Boot – HOBO Mila Leather Clutch – LA MENO Perfect Set Hoop Earrings

Booties with dress: Maxi dress

Booties also look great worn with your maxi dresses. Mix up your styles by wearing a formal dress and casual boots.

Karen Millen Marble Slinky Jacquard Knit Maxi Dress – COS Leather Chelsea Boots – Tory Burch Kira Chevron Convertible Shoulder Bag – Karine Sultan Cultured Peacock Pearl Drop Earrings

Mel @curvycartel above matches her booties to her sunglasses.

Check out this maxi dress (other options here and here) that you can wear with this similar vest, booties (another option here) and sunglasses.

Matchy matchy booties

Matching your booties to your accessories is a great way to achieve a stylish, coherent look. You ould match your scarf to your boots.

Karen Millen Merino Wool Silk Cuff Maxi Knit Dress – Franco Sarto Stevie Bootie – HOBO Mila Leather Clutch – Karine Sultan Cultured Peacock Pearl Drop Earrings – AllSaints Tie Dye Oblong Modal Scarf

Booties with dresses for summer

If you don’t want to put away your summer dresses, you can just swap your sandals for booties, and add a cardigan or jacket.

BLANKNYC Faux Suede Moto Jacket – Karen Millen Floral Shirred Detail Woven Maxi Dress – LifeStride Dynasty Booties – Ted Baker London Equesa Equestrian Bucklet Leather Bucket Bag – LA MENO Perfect Set Hoop Earrings

How to wear booties: A capsule wardrobe

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.

shop the Outfits with booties above here:

Below you can see more ideas on how to wear your booties, also featuring pants and jeans.

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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Feature image by Nancy @nancysstyle

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