Inside: Examples of how to wear a pleated skirt with sneakers.

There’s nothing like a good pleated skirt for spring. And with skirting being such a big trend this year, both maxi and mini, it’s not only high fashion but also so cute for the year. It’s great for any and every season, and it all depends on how you style it. Late winter and early spring is the perfect time to break the sneakers back out after a winter full of boots and layered leggings.

If you don’t naturally have the eye for streetwear and pairing dressy pieces with casual pieces like sneakers, let me help you out.

It’s a balancing act, but at the same time it’s such an effortless look. Once you get used to how it all looks together and accept the new way of styling these classic pieces in a not so classic look, it will be a little easier to casually throw these pieces together.

If this isn’t a look you normally reach for and want some help doing so, let’s get into it!

Four girls wearing cute outfits showing how to wear pleated skirt with sneakers

What Style Of Sneakers?

It’s going to be hard to go wrong with any kind of sneaker you choose for this outfit. It’s a simple style, and there are very few sneakers that wouldn’t mix well with a pleated skirt.

The maxi skirts have all the versatility.

You can grab your staple white sneakers you wear with everything and make a staple new, or you can track down a cool pair of statement sneakers and make this look a little bolder.

Sneaker heads likely already have the game on lock and are ready to roll with whatever they have in their closets already. But there’s always an excuse to buy new sneakers too.. And if this is it, take advantage!

Online shops like StockX and Grailed have amazing sneaker options of sold out and limited editions, if you’re browsing for something new and unique it’s worth checking out.

Whether you’re looking to throw on your trusty staple sneakers or make a new statement, any sneaker will do!

If you go the pleated mini skirt route, it’s a more specific style for sure. I would go with the more preppy vibes for this skirt.

A classic tennis shoe or a standard white leather sneaker for the prep school style that naturally comes with the skirt.

High top Converse or Vans will always add a youthful aesthetic.

What Kind Of Pleated Skirt To Pick?

2023 is bringing us many skirting options to add to our closets. We’ve been rocking with the micro mini skirt since the Y2K comeback of 2020, and that brought the 70’s inspired 2000’s with it. The 70s are obviously influenced by peasant vibes and relaxed casual glamor.

As we move into the new year and new trends, we’re seeing the preppy movement return and take over the market as well. The two aesthetics converge into what we’re seeing now as an edgy preppy street style. A peasant style maxi skirt is hot right now too, especially paired with something more sleek and preppy. We’re back to that concept of contrast & learning how to wear pleated skirt with sneakers is a great way to practice this.

Midi skirts have been the movement lately, but the maxi skirts are the hot new piece, making the midi a skirt of yesteryear. As they’ve been popular recently, many of the inspiration photos will feature a midi style, but I super encourage you to give the maxi thing a try. Midi was the way we eased into maxi, and I think you’re ready. It’s a statement to go all maxi, but you can do it and love it.

A pleated mini skirt fits right into the preppy aesthetic that’s been thrown at us this year. It’s a total throwback to the years when Gossip Girl ruled our TV’s and I couldn’t love the trend any more than I already do.

Throwing on a pleated mini skirt with your favorite pair of preppy sneakers is just what I love to see, with a little cropped sweater and you look like you belong court side on the tennis court.

It can be street too, a very summer aesthetic. With a pair of Nike Dunks and a graphic tee, and you’re ready to roll out on your morning stroll to the coffee shop this summer.

There are so many ways you can take these looks, but be sure to start with the most simple basics, and get a little edgy with it! Go for a pleated maxi or a pleated mini. Either way, go extreme and go pleated!

Favorite Pieces Shoes To Pair With Skirts

Okay so we’ve already decided that we want the sneakers to either be basic or statement, and the skirt to be either a mini or maxi. But once you’ve decided on these pieces, how do you know what to put with it? We will look at some photo examples later, of course, as we always do, but we are going to talk through some ideas as well.

In the winter, you’ll always want a good sweater for an outfit like this, or even a hoodie if you’re really committed to the street style aesthetic. There’s not really a right or wrong answer, there’s not really a too casual or too dressy way to wear this. However I would say stay away from anything that has a very classic, traditional, or homely feel to it, simply for the fact that it will start to look like a different aesthetic entirely than the classic street cute that we’re going for in this outfit.

A silk button up blouse will always be cool, and you can’t go wrong with a plain baby tee.

If the proportions work correctly, (which this is something you’ll have to figure out while styling the outfit, and looking at it with a trained eye) but a long oversized tee with the long maxi skirt, and the sneakers is a really cool look that the New York streets are loving these days. It might take a little bit to get used to because it sounds super unflattering. But if it’s the right tee shirt, it’ll look just right!

These are some of my favorite items to pair together with a pleated skirt and sneakers.

Two girls in street style oufits

How To Wear A Pleated Skirt With Sneakers

1. Silver Skirt
2. Chunky Sneaker
3. Long Sweater
4. Graphic
5. Button Down

Preppy girl outfit

Mini Skirts

6. University Prep
7. White Tones
8. Plaid
9. 2000’s

Two girls in long skirts and sneakers

Long Skirts

10. Metallic
11. GAP Tee
12. Tied Tee
13. Easy


14. Casual
15. Pinks
16. Vintage Vibe
17. Grayscale

As street style continues to take over our lives and closets, it starts to become more of a normal aesthetic to take on rather than a super edgy concept. Now it feels like sneakers naturally go with anything and everything. You don’t have to sweat it if you don’t have the right shoes for an outfit, a sneaker will do just fine and we’ve shown you exactly how to wear pleated skirt with sneakers for the most pulled together, but still effortless summer look around!

And as maxi skirts dominate this season and next, it just feels natural to at least try out pairing them together. Maybe you love it, maybe you hate it, and maybe you have to play with it a bit to decide. Either way, you’ll look crazy trendy.

Tap into your inner Pinterest style goddess and New York Fashion Week street style icon. It’s a color outfit that looks amazing and trendy without much effort. And effortless cool is always the goal, right?

Do you and your boo need some new photos together? Here are 57 easy outfits to help coordinate the day a little bit and get some of those beautiful snapshots.

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