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.
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.
For an elongating effect: Black booties outfit
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.
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.
Abi (above) wears her cropped jeans with booties, and leaves a little ankle showing.
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 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.
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:
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.
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.
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.
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.
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.
Pointed toe boots
These booties below from Sole Society have an on-trend slouch at the back.
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.
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.
Texture was a key element of the winter and fall 2020 shoe trends. In particular, reptilian textures featured heavily on the catwalks.
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.
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.
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.
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.
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.
Lou (above) wears her coated leggings with an oversized shirt and lace-up boots.
Outfit 2: Eileen Fisher ballet neck tunic – Ellen Tracy plaid belted coat – Lyssé denim leggings – BC ‘Anything Is Possible’ vegan leather bootie – Madewell leather tote – Karine Sultan pendant necklace
Ankle boots with jeans and pants
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.
How to wear ankle boots with skirts
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.
Dresses with ankle 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 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.
Outfit 1: AWARE by VERO MODA dress mock neck midi dress – BLANKNYC suede moto jacket – DailyShoes western cowboy bootie – rag & bone shopper tote – Kate Spade New York stud earrings – Halogen rib cashmere scarf
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
How have you been wearing your booties this season? I’d love to hear your own tips on how to wear booties.
- The Best Winter Boots For Women: Stylish Winter Boots That You Can’t Wait To Wear
- Best Shoes With Arch Support – Comfortable Walking Shoes To Walk In All Day!
- The Best Wide Calf Boots For Winter And Fall
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Feature image by Jill
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