10 Best Shoes To Wear With Skater Skirts & Dresses

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Skater skirts are an iconic wardrobe piece that’s well-loved by most women. If you’re having a hard time styling this piece, have a look at our guide on the best shoes to wear with skater skirts and dresses.

If you were around social media during 2013 through 2015, then you are most likely very familiar with the skater skirt and dress craze – it had the entire world on a chokehold, and #OOTDs (outfit of the days) with skater skirts were popping up left and right.

Skater skirts back then became popular thanks to Lookbook and Tumblr influencers who were seen rocking that preppy, cool-girl vibe. Add in a pair of sneakers and there’s the perfect outfit!

Pink tennis skater skirt with white tank and white sneakers
Get this skirt on Princess Polly

Skater skirts are a subset of A-line skirts (or circle skirts) that hug the waist and flare out. They have been around for decades, and remain one of the most popular styles of skirts right now.

Although you’d be excused to think that the name of this skirt has something to do with skateboarding, that’s not where the name derives from. It’s actually a type of skirt is worn by figure skaters.

If you want to wear your skater skirt with confidence, it is important to know what shoes flatter it the most. In this article, we will discuss the 10 best shoes to wear with skater skirts and dresses, as well as share some of our favorite outfits!

What Shoes To Wear With Skater Skirts & Dresses

1. Sneakers

What Shoes To Wear With Skater Skirts: White FILA sneakers
Get these sneakers on Lulus

Sneakers are a great option for a casual look and they are a good match with skater skirts too! You can wear any type of sneakers from Converse All-Stars to Nike Air Maxes.

While sneakers in any color work great, we are partial to the classic white low-top sneakers.

To create the perfect look, simply wear a white top, a black skater skirt (or a neutral skater skirt) along with a pair of sneakers. Optionally, add in a denim jacket to keep you warm!

White sneakers paired with basic tees and a mini skater skirt will give off that effortless cool-girl vibe that we all love! Pairing cute high tops adds extra height while still remaining comfortable enough for everyday activities like walking around town shopping or grabbing coffee at Starbucks.

2. Combat Boots

What Shoes To Wear With Skater Skirts: Black lace up combat boots
Get these boots on ASOS

Combat boots are a great way to add edge to any outfit, and they look especially good when paired with a skater skirt. You can wear them with skirts of all lengths, but we recommend pairing them with short skater skirts that show off the boot’s cool detailing.

For a trendy look, wear a white crop top, a maroon skater skirt, a pair of your favorite lace-up combat boots, and a black leather jacket. If the weather is chilly, you can also wear black tights underneath your skirt.

Combat boots are perfect for those days when you want to feel edgy and stylish without trying too hard. They go well with almost any color palette, so it is easy to mix and match different tops and bottoms with this shoe style.

If black combat boots aren’t for you, more feminine beige lace-up boots will do the job too.

3. Ballet Flats

What Shoes To Wear With Skater Skirts: Nude flats with gold hardware
Get these flats on Lulus

Ballet flats are comfortable enough for everyday wear and look good with most clothing items, skater skirts being no different. Pair this shoe style when need shoes that are comfortable to wear for the whole day, and look cute on your feet.

You can find ballet flats in all colors, so it’s easy to pair them with any outfit for a sweet look. We recommend pairing these shoes with shoulder tops in floral prints for a feminine vibe in the summer.

Ballet shoes can be worn during both day or night time occasions. You can wear them with mini skirts, or even a knee-length skirt: your options are limitless!

4. Ankle Boots

What Shoes To Wear With Skater Skirts: Black ankle boots
Get these boots on ASOS

Try to prove us wrong: ankle boots are a fashion staple! These booties are stylish, practical, comfortable…. and a great way to add some edge to any outfit, especially when paired with skater skirts.

You can wear them in all kinds of styles and colors, so it’s easy to mix and match different tops to bottoms with this shoe style!

Ankle boots are perfect for those days when you want to add a bit of height to your outfit and look good without trying too hard; they go well with almost any color palette so mixing and matching is easy! If you want, you can also wear these booties with skater dresses instead.

5. Pumps

What Shoes To Wear With Skater Skirts: Brown pumps
Get this pair on Lulus

Pumps are a classic shoe style that always looks good with any type of skirt, and this includes skater skirts of all lengths. You can wear them in all colors and styles, as long as they match the rest of your outfit.

For a business casual outfit fit for the office, why not go for a houndstooth skater skirt paired with classic pumps and a blazer of your choice? Pumps are the perfect shoes for you if you want to feel extra glamorous and don’t need to do much walking during the day.

If pumps aren’t your thing, you can also opt for different styles of high heels as well – stiletto heels, strappy heels, and even block heels.

6. Knee-High Boots

What Shoes To Wear With Skater Skirts: Beige knee high boots
Get these boots on ASOS

Knee-high boots are a great way to add some edge and glamour to any outfit, especially during the fall and winter seasons!

For a gorgeous look, we recommend wearing a pair of knee-high boots with a black leather skater skirt and a turtleneck with long sleeves.

7. Mary Janes

What Shoes To Wear With Skater Skirts: Burgundy mary jane platforms
Get these shoes on ASOS

We are totally in love with Mary Janes! Mary Janes are a classic shoe style that made a comeback in 2021, and are projected to stay at the forefront of fashion well into 2022.

These school-girl-type shoes always look good with skater skirts, especially if you’re going for a preppy look. You can opt to wear this with knee-high socks to complete the aesthetic.

Owing to the school-uniform-inspired nature of the shoes, the shoe style usually has a low platform or block heel which makes them quite comfortable to wear.

If you love wearing heels but hate how painful they get after extended periods of walking around town then opt for MJs instead – their low profile design means that there is no pressure on any part of your foot while still giving off a stylish look!

8. Platforms

What Shoes To Wear With Skater Skirts: Blue chunky heels platforms
Get these shoes on ASOS

Platforms heels are another shoe type that has come back in a big way in the last year or so – just open up Instagram and you’ll see fashion influencers like Lailli Mirza rocking cute platforms from Valentino and other major fashion houses.

Platform heels come in different styles and heel lengths, so you can totally go crazy with this trend. If you’re going for a retro, Japanese cyberpunk or Lolita aesthetic, then high-heel platforms are the way to go! Wear this with black stockings for added glam.

9. Thigh-High Boots

What Shoes To Wear With Skater Skirts: Black leather thigh high boots
Get these shoes on Nasty Gal

Thigh-high boots are perfect if you have a mini skater skirt in your wardrobe. You can pair the two to create an endless array of cute, preppy fall and winter looks with your favorite sweaters.

10. Wedges

What Shoes To Wear With Skater Skirts: White espadrille wedges
Get these shoes on ASOS

Lastly, wedges are a cute addition to your skater skirt outfit. There are sneaker wedges, boot wedges, and espadrille wedges, so you have lots of options to wear with your skater skirt!

If you’re going for a feminine look, we suggest wearing espadrille wedges. These would look super cute, especially with a midi or a maxi skater skirt.

Commonly Asked Questions

Are skater skirts still in style?

Yes! Skater skirts are still popular and will continue to be for years to come. The best way to wear this trend is with sneakers, sandals, flats, or heels – whatever shoes you choose make sure they complement your outfit well!

Are skater skirts work appropriate?

This depends on the company and what they allow employees to wear. Also, the length of your skater skirt plays a vital role.

If your office allows casual attire then a short skater skirt would be fine. However, to be on the safe side, we recommend opting for a skater skirt that is more formal, like a midi-length or knee-length skater skirt with a houndstooth or gingham pattern. Alternatively, you can also opt for a skater dress.


So there you have it: the ten best shoes to wear with skater skirts and dresses! Whether you’re looking for edgy boots, glamorous pumps, or something more comfortable like sneakers or Mary Janes, we hope that you found the perfect way to style your skirt.

Also, remember that while these are our best tips, fashion is meant to be fun, and “rules”, especially “fashion rules” can definitely be broken. So, make sure you have fun when experimenting with your looks!

We hope you found this style guide helpful! If you’re still looking for more fashion inspo, check the posts down below.

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