The Effortless Way to Style Sneakers with Skirts

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Hi, I'm Chelsey

Welcome back! Before diving in with today’s style advice, are you reading this post on a desktop? If not, you’re missing out! I’ve gone back and forth about changing my site design over the past month, but I ultimately really love what I’m using so I don’t want to switch it up just yet. That being said, I have made a few tweaks to keep it fresh, totally revamped the capsule wardrobe freebie, and have updated the look and feel of my newsletter! I’m also bringing back the beloved style hub soon, so make sure you opt-in here so you can have access and be notified when it’s available! Okay, enough with the announcements!

texas influencers fashion bloggers style sneakers with skirts

Let’s talk about skirts and sneakers. Admittedly, this pairing is something I wasn’t really a fan of until a few years ago. Longtime readers may recall that I actually wrote a blog post sharing 5 tips that will help you try new trends, and one of those tips I still use to this day: TRY. IT. ON. Lo and behold, that’s how I grew to appreciate the sneaker and skirt combination.

In general, I’m not a big wearer of sneakers but sometimes the weather calls for something in between a sandal and a boot. After pairing sneakers with a dress last year in an effort to get inspired for my California trip, I started to understand the appeal. Needless to say, I’m still quite particular and have learned what does and doesn’t go together. If you want to style sneakers with skirts or dresses, try one of the 3 style tips below.

how to style sneakers with dresses


Nordstrom BP tee | Zara denim jacket | Nasty Gal snake print skirt | Converse sneakers | Quay Australia high key sunglasses | Topshop bag | Jenny Bird earrings

The Fashionable Way to Style Sneakers with Skirts

1. Keep it clean with white.

White sneakers, if you recall, are a style staple to keep in your closet at all times. Not surprisingly, my biggest tip for wearing skirts and sneakers together is to err on the lighter side. When in doubt, wear white sneakers with your skirt. Not only does it give you the freedom to wear any colorful or printed skirt without worrying about them clashing, but there’s a very high chance you already own a pair of white sneakers. Increase their ROI and use your white sneakers for things outside of just gym or loungewear. A white sneaker takes the guesswork out of putting the outfit together, and 9 times out of 10, it adds the right amount of street to your look.

black fashion bloggers in texas style sneakers with skirts

2. Make it chic yet wearable with a flat sole.

This is your friendly reminder that there are a few tweaks needed to make runway trends wearable for the everyday person. Remember when sneakers with dresses first became trendy and pretty much the only people wearing the trend were the NY fashion girls who had a purpose to wear comfortable shoes with their otherwise business casual outfits? What a time.

The look certainly wasn’t for me, but this is when knowing your personal style becomes critical to your fashion sense. If you only ride the trend wave and wear what you see, you may have tried out the early versions of this trend only to realize it didn’t quite work for you. (If it did, more power to you!) Colorful, chunky sneakers with all the add-ons can look extremely busy when paired with a skirt. Strip away some of the flashiness from the “fashionable” introduction of a trend to make it wearable for your lifestyle. With sneakers, the chunky heel and multi-color designs are a bit on the edgier side. To make it everyday chic, stick with sneakers that have a low (or no) heel and a flat sole. There’s something about the flat-soled sneaker as opposed to one with any sort of arch or unlevel sole that is just made for your skirts. Try it on and thank me later.

style sneakers with skirts outfit ideas

3. Balance the sneakers with a casual top.

Moving into the actual clothing, it’s best to balance out the sneakers with a casual top. You can absolutely pair a silk skirt, pleated skirt, or snakeprint skirt with sneakers and still pull off a beautiful outfit. The key is all in which top you select. The three skirts I mentioned are more on the dressy side and can be paired with silk blouses, but save those for when you want to wear heels or boots. A cotton tee or chunky sweater are more relaxed and tie the outfit together to create a cohesive look. If you want a little flair with your tee, pick a fun graphic tee or layer on a boyfriend blazer.

The Best Sneakers to Pair with Dresses and Skirts

Naturally, I didn’t want to talk about how to style sneakers with skirts and just end it without any options. Personally, no sneaker I own looks as good with a skirt or a dress as my classic low-top Converse. I don’t own the high-tops but even those will look great with a skirt. The shoe is so minimal and as flat as you can get, which makes it extremely versatile and perfect for this trend. With that being said, I’ve expanded beyond just Converse and curated a selection of shoes below to give you a starting point.

What do you think about styling sneakers with skirts?

Photography by @desertwillowstudios.

Thank you to Jackie for these gorgeous photos! If you’re a Texas fashion blogger in the Austin/San Antonio area, check out Desert Willow Studios for your photography needs! 

Comments +

  1. Darianne says:

    I find converse to be the most versatile sneaker to style. I’m not much of a sneaker person. I love wearing booties and other forms of heels, but I can admit to wearing converse just to keep my style casual when heels just won’t do. x

    Darianne |

    • Chelsey says:

      Totally agree, there’s a reason why converse have withstood the test of time generation after generation! The design is so simple yet effective at the same time.


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