The 8 Best Shoes to Wear With Skater Dresses: 7+ Outfit Ideas
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  • Writer's pictureBrenda

The 8 Best Shoes to Wear With Skater Dresses: 7+ Outfit Ideas

Updated: Feb 9

I'm definitely one of the people who was excited when the skater dress trend really took off some 7-8 years ago. As a woman who is more bottom heavy, wearing dresses and skirts that were less "distracting" in the office was a constant challenge I faced. It was not my fault my curves were found to be distracting and I was made to feel bad for it but that's a story for another day.

Skater skirts and dresses were among my go-to outfit ideas during this period because they would flare out from the waist and not hug my curves like pencil skirts and dresses do. Before jumping into the different ways you can style your skater dress, I would like to answer some common questions regarding this style.


Amazon has probably my favorite style of skater dresses in the perfect length which is this one HERE

Why are they called "skater" skirts or dresses?

If you're wondering how this style of skirt (and dress) got its name, I have an interesting fact for you: skater skirts and dresses are fitted at the natural waist and flare out into an A-line silhouette. These skirts resemble the costumes of figure skaters, hence the name. Skater skirts and dresses also typically stop above the knee, creating a more youthful and feminine look.

Do skater skirts and dresses have to be short?

While browsing other blogs and websites, I did note that most of the images of skater outfits involved short skirts and dresses but I am here to tell you that although most of them do hit above the knee, you can still rock a longer skater skirt outfit. There are longer versions of this clothing available and I would be providing links to these.

Can I wear a skater dress in the winter?

The short answer to that would be yes. However, you would have to style your outfit the proper way for the cold weather. The right pair of boots as well as a sweater or cardigan with long sleeves are items that would be necessary to carry your skater dress or skirt into the winter months.

Are skater dresses still "in"?

In my opinion, any style can be in fashion. It all depends on the person wearing it. Look at how mom jeans and fanny packs have made a comeback. As long as you have the confidence to pull it off, any trend could be made modern and wearable. Skater dresses and skater skirts in particular are loved so much because they look great on any body type- it just depends on how you style them.

Now that we've gotten those questions out of the way, let's take a look into the different footwear to go with those pretty skater dresses and skirts in your closet!

You may find that a lot of the footwear is similar to those from my post on the best shoes to wear with a maxi skirt and that's because I'm here to make your items work for you. You should be able to get multiple wears from the same key pieces in your closet to create different styles so I'm here to show you how.

*Disclosure: This post may contain affiliate links, which means that I get a small commission if you decide to make a purchase through the links, at no cost to you.

1) Skater dresses with loafers

Loafers are a step up from flats in terms of formality. I really enjoy pairing my skater skirts and dresses with a pair of black tights and loafers for a day at the office. If it's a little chilly in the building, I wrap a cardigan over my shoulders. This is such a preppy look that is also chic and work-appropriate. Consider going with a floral skater dress during the warmer months to brighten up your outfit.

Image source here

Your loafers could be in a neutral color or match it to one of the colors of the flowers on your dress. If your dress is shorter in length, don't forget your biker shorts underneath! This outfit could also be worn to church or any other settings requiring a business casual dress code be followed.

2) Skater dresses with white sneakers

If you're aiming for a more casual look with your skater dress or skirt, then adding a pair of sneakers is an easy way to do so. You already know how much of a fan of white sneakers I am (seeing as I've included them on every outfit idea list) and so in my opinion, they're a great way to make your skater outfit everyday wear.

These are my favorite Vans HERE

Image source here

For some additional warmth with this chic casual outfit, throw on a denim jacket and you're good to go. It's just fascinating to me how a pair of white sneakers makes any dress or skirt outfit look cool and casual.

3) Skater dresses with chunky heels

I had to specifically mention chunky heels and not just high heels because platform heels are a great option to go with if you're going for a more fun and flirty look. During the Summer days, if you're thinking of trying out different looks for casual occasions, you may want to give this one a shot. The chunky heels and skater look works especially well with mini skirts or mini skater dresses to create a sexualized school girl look.

Image source here

Think of Mary Janes and other platform heels. To really take the school girl theme even further, consider adding a pair of knee-high socks to your overall look. This would give you a cool-girl vibe, reminiscent of shows like Clueless (90's baby over here).

4) Skater dresses with ankle boots

When the colder months come rolling along, a great way to bring your skater dresses into the new, colder season is by switching up your footwear and adding outerwear. In the Fall, I love to add a pair of tights or leggings to my skater dress and wear my favorite black ankle boots with my skater dress. A black skater skirt paired with some combat boots like the Dr. Martens would make for some great Fall casual wear.

You can play around with boots in different colors depending on the color of your skater skirt or dress. A green skater skirt for example would look great with a pair of white ankle boots. I have an entire post dedicated to styling white boots and so you may want to check that out next. If your skater dress has floral prints, then many colors of boots would pair nicely with it. All you would need to do is pick a color on the dress and choose a pair of ankle boots in the same or similar color to match. You could choose a different color each time you wear the same dress and it would be like a new look every time.

Image source here

5) Skater dresses with higher boots

Adding a pair of knee-high boots to your skater dress look is a great way to create a stylish look with short skater skirts or dresses. The shorter length of the dress or skirt allows for the boots to be on full display and also make the legs appear longer. If you're one of the fortunate ones to have claves and thighs can fit into thigh-high boots, then by all means, try try out this perfect combination in the Fall.

Images source here

You could wear a nice oversized sweater with your skirt for a chic Fall look you can wear to attend special occasions. A black leather jacket would make a great outerwear of choice to bring this look together. For really formal occasions during the winter season, try wearing a black skater dress with knee or thigh-high boots and a statement necklace.

The black dress already screams formality and the boots assist in keeping you warm but stylish. The right accessories then elevate the look, making it perfect for a formal event.

6) Skater dresses with flats

A pair of flats is a global fashion staple and so there was no way this list would complete without them. Regardless of the type of dress or skirt you're pulling off, if you don't feel like teetering around in some heels, a pair of flats is a great alternative. You could most definitely rock this look to work, for a meet up with the girls during the day time or even on a date.

Image source here

During the colder months, your flats could be swapped for either a flat ankle boot or flat knee boots for a warmer look. A longer skater dress with a pair of flats makes for comfortable formal wear when you're not in the mood for heels. Just be sure to invest in a great pair of flats in a neutral color.

7) Skater dresses with stiletto heels

The best way to take your skater dress look up a notch is with a pair of high heels. Stiletto heels in particular are the ultimate sexy shoe and and regardless of your body shape, they're guaranteed to make you appear taller, leaner and more confident. The right shoes make or break the outfit each and every time.

Get the look HERE

The next time you're trying to make your dress even more formal, add a white blazer on top and watch the heads turn. Another good idea is to add a cardigan on top of your skater outfit and a skinny belt. This is a great last minute solution to instantly make your outfit more formal.

8) Skater dress with open-toe sandals

Headed to the beach or a a pool party? Then this option is definitely for you. A pair of open toe sandals, whether heeled or un-heeled looks great with a skater dress in a similar way a pair of heels do. The open toe makes the look a little casual but if you go for a heeled sandal, then you make it look more dressy. Feel free to drape your favorite leather jacket across your shoulders for a more sassy look.

So which of these pairings was your favorite? Don't let the fashion industry dictate when you have to stop wearing certain items. From this list, I hope you have come to see that some great skater dress looks can be pulled off during the colder months.

Skater skirts and dresses can come in all types of fabrics and colors as well as lengths but how you style them would determine what kind of event they can be worn to.

Let me know if you have any questions.

Do check out my post: 6 chic ways to wear a wrap dress for some more outfit inspiration.

I also have a post, 5 ways to wear a dress in the winter if you're bent on wearing dresses during the winter months.

For some shoe inspiration the next time you're wearing a black cocktail dress, check out: 10 shoes to wear with a black cocktail dress.

Until the next post,



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