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How To Wear Midi Skirts With Ankle Boots? 8 Iconic Ideas

How To Wear Midi Skirts With Ankle Boots? 8 Iconic Ideas

We could blame the whole thing on the return of some old-school classics such as Elvis and Blonde. We could blame the fashion shows that started conversations about comeback trends. Whatever the case may be, midi skirts are back and they’re here to stay. How, then, do you wear midi skirts with ankle boots?

Retro, comeback fashion seems to be the trend of 2022 and we’re here for that.

Bold colors, oversized silhouettes, snatched waists, polka dot patterns, and (of course) midi skirts seem to have left a mark on the fashion shows of some of the most popular designers such as Gucci, Mark Jacobs, Proenza Schouler, and Bottega Veneta.

Oh, the fall fashion predictions made things clear. According to them, the 50s, 60s, and 70s trends were back and ready to take over the world with longer hemlines, pussy bow blouses, and headscarves.

And, our favorite fashion babes didn’t take long before they started wearing these trends outside – the Hadid sisters, Hailey Bieber, and Zandaya are only some of them. We’re all thinking the same thing, aren’t we?

How do we channel our inner Zandaya and wear midi skirts with ankle boots without looking frumpy? How do we achieve the effortless flowingness of a long, luscious skirt without having to grow longer limbs?

Worry not, we’re bringing you everything you need to know about styling this fall’s favorite staple – the midi skirt.

What are midi skirts? 

How To Wear Midi Skirts With Ankle Boots? 8 Iconic Ideas

When Milan Fashion Week hinted at the rising popularity of silky, satin skirts, tartan pleated skirts, and patchwork denim skirts, we collectively gasped. We’ve definitely been waiting for longer hemlines to become a thing because we’ve grown bored of fabrics that don’t go past our thighs.

And, luckily for us, our favorite designers heard our pleas and decided to bring back the midi skirt as the staple piece of every woman’s wardrobe. What constitutes a midi skirt, though? What other styles of skirts are there?

First things first, when we’re talking about different types of skirts (based on length), we’re referring to mini skirts, midi skirts, and maxi skirts. Within these length categories, we also talk about a variety of styles such as the pencil skirt, pleated skirt, satin slip skirt, A-line skirt, and skater skirt.

Therefore, a midi skirt would be a skirt that falls somewhere between your knees and your ankles. The “perfect” midi length falls right above the swell of the calf or right below the calf.

That means that the right length of a midi skirt for you should show your ankles when styled with ankle boots. Now that we understand the length of the midi skirt, we can move on to the history behind it and see what made midi skirts as popular as they are (and once were).

Though that might sound strange, midi skirts were a response to the 60s obsession with mini skirts, long legs, and Twiggy. Midi skirts offered women a chance to look polished, elegant, and fashion-forward without revealing too much.

Of course, they featured the typical A-line style and were combined with platform shoes and statement accessories. And, once the midi skirt appeared on the big screen with Faye Dunaway’s role in Bonnie and Clyde, the rest was history.

What’s the best way to style a midi skirt?

Midi skirts are versatile, easy to style, and comfortable. Whether you’re trying to figure out what to wear for a weekend getaway with your girlfriends. Whether you’re screaming at the top of your lungs “I have nothing to wear to work!” while surrounded by piles and piles of clothes.

Choose the midi skirt. Always choose the midi skirt.

We can’t overlook the simplicity of styling a midi skirt, especially because Milan Fashion Week featured pretty much nothing other than our favorite style of skirt.

Sure, the Prada feather-embellished skirt that took the runway by storm might be out of our budget. But, there are a bunch of other alternatives that would create the same vibe.

Therefore, you’re trying to figure out how to style your midi skirts. When wearing midi skirts with ankle boots, think of the silhouette you’re trying to create.

For a carefree outfit with an edge combine a satin midi skirt with an oversized, chunky cardigan and combat boots. Add gold accents with statement earrings, sunglasses, and a leather handbag.

For a timeless, elegant ensemble choose a pleated midi skirt paired with a figure-hugging turtleneck, suede boots, and a long, earth-toned trenchcoat.

And, for something out of the ordinary, experiment with a graphic tee, a leopard print (or even tie-die) midi skirt, and leather loafers or leather ankle boots. When you’re styling a midi skirt, the only thing you need to think about seems to be the silhouette.

When you don’t choose the right length, fabric, or pattern, you risk having your midi skirt appear unflattering, frumpy, and fraught. Opt for a style that works for you and you shouldn’t have that much trouble picking out the rest of the outfit.

How to wear midi skirts with ankle boots?

1. Stiletto ankle boots

How To Wear Midi Skirts With Ankle Boots? 8 Iconic Ideas

It is no secret that midi skirts, whatever fabric or pattern you decide on, go with ankle boots more than any other footwear.

There’s something about the contrast between the length of the skirt and the height of the boot that makes everyone appear more fashionable, put-together, and modern.

Remember when Victoria Beckham had her Cinderella moment a couple of months ago when she combined a body-skimming, blue midi dress with embellished, mesh stiletto boots?

Turns out you don’t have to be Victoria Beckham to wear something similar to work, to dinner with friends, or a date night. Nordstrom carries a pair of Michael Kors pointed-toe stiletto booties that look exactly like the ones she wore for a fraction of the price.

Given that you’re looking for something more budget-friendly, we suggest you take a peep at the Zara high-heeled, studded ankle boots or the Mango pointed-toe ankle boots (without the studs, though).

2. Pointed-toe ankle boots

While we’re on the topic of pointed-toe boots, we might as well touch upon the fact that they’re able to make your legs look longer, your outfits more fashion-forward, and your entire posture better. Trust me, midi skirts with ankle boots never looked better!

Pointed-toe ankle boots are the perfect shoe to wear with a midi skirt. Especially when you’re trying to look taller without wearing 6-inch high heels. And, when you’re wearing these ankle boots, you don’t have to worry about the style of the shoe that much.

Whether they’re high-heeled, block-heeled, or completely flat, they’re bound to have the same effect on the rest of your outfit. Make sure you stay within the color palette to further elongate your figure, and you’re good to go.

To offer you a couple of styling suggestions, decide on the vibe you’re going for. For a muted, nonchalant combination, wear a knitted skirt/sweater set and a pair of block-heeled booties that aren’t too high for comfort. Steve Madden makes a great option called the Abriel pointed-toe bootie.

For something a bit more “out there,” don’t shy away from combining a leather skirt, a cashmere sweater, and a pair of mesh pointed-toe boots like the ones Karl Lagerfeld carries. Whatever you decide to go for, pointed-toe ankle boots are bound to make you stand out.

3. Sock ankle boots

How To Wear Midi Skirts With Ankle Boots? 8 Iconic Ideas

Sock boots have never stopped trending because they’re that flattering. Everybody wants to wear a boot that gives off the effect of bare, sculpted legs with the addition of high heels.

Of course, everybody loves combining them with skirts, dresses, and other outfits that show them off.

Perhaps you’re wondering how to wear midi skirts with ankle boots? Maybe it’s because you’re not sure whether the ensemble would be flattering on you. Well, wonder no more.

Sock ankle boots are bound to make your legs look longer and slimmer, which means they’re bound to make you look like you came straight off the runway.

Go for sock boots that are the same (or similar) color as your skirt for that elongated moment. Stuart Weitzman Sock Booties are on sale at Nordstrom – and, they happen to carry a bunch of shades you can choose from.

Our favorites have to be the burgundy stiletto ones because they would work great with the current fall fashion trends.

4. Lace-up ankle boots

Here’s the tea you might not be ready for, midi skirts are some of the most versatile pieces of clothing. And, we’re not talking about the fact you can wear them for every season, every occasion, and every event when you don’t know what to wear.

Actually, we’re talking about the fact that you can dress them down, dress them up, or give them an edge with the right shoes and accessories.

Whether you’re getting ready for Coachella. Whether you’re experimenting with the bohemian, free-spirited trends that have been circling for the past couple of months. Wear a pair of lace-up ankle boots (like the Chloé May leather ankle boots) with a flowy, frilly boho skirt and you’re good to go.

However, even when you’re not thinking of music festivals when you’re creating your outfits, you can’t go wrong with lace-up ankle boots.

Maybe go for the Schutz Tennie pointed-toe, lace-up boots, and a satin, slip skirt for a night out. Or, go for the Tory Burch Miller mixed materials boots for work.

5. Cowboy boots

How To Wear Midi Skirts With Ankle Boots? 8 Iconic Ideas

On the off chance that we forgot to discuss the fact that bohemian fashion appears to be making a comeback, we’re sorry.

But, we’re not sorry that we get rock those cowboy boots that have been collecting dust because we’ve never dared to wear them outside of Halloween.

Boho midi skirts and cowboy boots are a classic. The two can never go out of style, and we have fall fashion runways galore to attest to that fact.

Therefore, don’t shy away from trying out at least a couple of Zara’s and Mango’s flowy, floral skirts combined with chunky, knitted cardigans and cowboy boots.

And, even when you don’t have cowboy boots lying around, you won’t have a hard time getting your hands on a pair.

Ganni embroidered leather boots, Franco Sarto Liandra cowboy boots, and Isabel Marant Duerto leather boots are some of our favorites. However, you can go with whatever style speaks to your inner bohemian spirit.

6. Platform (or block-heeled) ankle boots

We adore the platform shoe trend and we couldn’t be more excited to suggest you wear platform boots with everything!

Whether you’re wondering what shoes to wear with midi skirts or how to wear midi skirts with ankle boots, the answer’s always the same – go for platform ankle boots.

And, we haven’t even brushed over the metallic, sparkly, embellished midi skirts that have been featured in every fashion magazine’s holiday edition.

Other than the very, very obvious stilettos, you can always style such a statement piece with platform boots to make even more of a statement.

Because of the popularity of Versace Medusa Aevitas platform pumps, platform shoes can be found anywhere you look.

Zara carries an affordable alternative to the Versace ones (yes, Versace also made the platform booties), but you can find them for a fraction of the price at Mango, Fashion Nova, and even Amazon.

Granted that you want to splurge a little and go for the designer ones, Botega Venetta, Stuart Weitzman, and Stella McCartney offer interesting ideas.

7. Chelsea boots

How To Wear Midi Skirts With Ankle Boots? 8 Iconic Ideas

Platform boots are fun, but how do you wear a midi skirt with ankle boots when you’re not looking to break an ankle?

Chelsea boots are famous (and on the throne for decades and decades) for a reason. Whenever you’re looking for a comfortable boot to wear with pretty much everything, Chelsea boots have your back.

Now, you probably know what Chelsea boots look like. They’re fitted, ankle boots with stretchy panels of fabric on the sides which makes them even more comfortable (and easy to slip on and off when needed).

Chelsea boots became known by that name because they were worn around the Chelsea area, a trendy part of London, during the 50s and 60s. And, these boots are easy to work with.

As long as you choose the right style for whatever vibe you’re going with, you shouldn’t face problems trying to wear them with skirts of any length. Nowadays, you can choose between flat or high-heeled Chelsea boots which should make your task even easier.

For a midi skirt, we suggest you go with Chelsea boots that are the same color as the skirt (for that elongated look). Steve Madden platform Chelsea boots, Mark Fisher Yale Chelsea boots, and Aquatalia Rosina Chelsea boots are the ones we would choose.

8. Chunky combat boots

Last but not least, we can’t forget about the chunky combat boots for girlies who are looking to take their fashion game a step further. Luckily, there are numerous styles you can choose from and decide which of them fits the mood you’re going for to a tee.

Whether you’re styling a polka dot patterned midi skirt, a metallic midi skirt, or even a leather midi skirt, chunky combat boots are there to add that je ne sais quoi element.

Kendall Jenner, Gigi Hadid, Hailey Bieber, and Emily Ratajkowski love their Dr. Martens and designer brands of chunky, lug-sole boots and wear them everywhere they go.

Now, you don’t have to go for the designer price (unless you want to) because Dr. Martens are on sale at Nordstrom as we speak. And, you can style them with your favorite midi skirt, a chunky sweater, and a leather jacket for that cool, moody look.

You can even wear them with a tulle skirt, a fitted blazer, and a chunky belt with gold accents for an editorial, front-of-the-runway-show look. Whichever style you’re gravitating towards, you can’t go wrong with chunky combat boots.