8 Best Shoes to Wear With Skirts

Pants and shorts are certainly wardrobe staples, but there’s something extra special about wearing a skirt. Maybe it’s the freedom of being able to feel the breeze. Maybe it’s the fun of spinning in a circle and watching the fabric billow out around you. It might just be how fabulous and fancy-free a skirt makes you feel.

Whatever your reason is for putting on a skirt, you’re probably also looking for the best shoes to wear with skirts. 

To find the right footwear for all your twirling and swirling, you’ll first want to explore the different types of shoes that pair well with skirts. Grab your favorite skirt from the closet and daydream about where you’ll be headed the next time you put it on. With a bit of inspiration, you’re sure to discover a pair of shoes that complement it perfectly.


Let’s start from the ground up. Flats for women are comfortable, maneuverable, and can help you stay light on your feet no matter what task you need to accomplish. While some flats work better with skirts than others, there are plenty of options to choose from.

Walk to the train, host a party, and stand up for what’s right with nary a wobble—the following selection of skirt-friendly comfortable flats for women will keep you outfitted in style all the while.

1. Espadrilles With a Little Lift

One of the challenges of wearing skirts is balancing the proportions of your outfit and keeping your lines long and flattering. If you have a short skirt and a flat shoe, it’s possible to end up looking a bit unbalanced. 

Luckily, this problem can easily be addressed with a careful selection of both pieces. 

Consider, for example, a mid-length skirt with a slit to the thigh—you’ll show a subtle flash of leg with every step, drawing the eye upwards. For the shoes, a pair of espadrille-style platforms will provide a bit of extra lift without making you teeter. 

What are espadrilles? They’re a multi-purpose shoe dating back to 14th Century Spain, traditionally featuring a rope or woven fiber sole. A pair of platform espadrilles are made out of heavy twill and wrapped with natural rope. They’ll stand up to a day full of action without sacrificing a single ounce of style, and pair perfectly with a flowy, slitted skirt, or a short athletic skort.

2. An Easy Breezy Pair of Slides

Our next shoe can lean formal or stay completely casual—the choice is entirely up to you.

Wear a pair of simple and stunning slides to a block party, to the botanical gardens, or just around the block for a cup of coffee. With a sophisticated toe-and-heel-baring silhouette, it’s easy to match slides with all kinds of skirts:

  • A brightly-colored, tiered maxi skirt is sure to impress, and will offer lively glimpses of the fashionable shoes on your feet.
  • Game, set, and match - a tennis skirt with slides to make your way to the court (or the courtside café) in style.
  • Dive into a day of leisure at the spa or the pool—slides work extremely well with a swimsuit and a sarong skirt. 
  • Slip them on to make a toast, then slip them off to sit on a blanket in the sun. You’ll be cool, comfortable, and classy, no matter what skirt you decide to wear slides with. 

3. A Sneaker With Some Serious Personality

Sneakers are a no-brainer when it comes to shoes that go with everything, and a classic pair of sneakers is always a dependable option for your skirted outfits. But for a new spin on the classic sock-hop style, try a puffy-soled sneaker, like the TOMS Mallow Heritage Canvas sneaker. And with ten colors to choose from, you’re sure to find a pair that suits your style. Opt for a classic white sneaker, or go bold with black leopard print. They’re ridiculously comfy, easy to slip on and off, and are often cut to reveal the top of the foot. With or without socks, it’s a shoe that will keep you dancing till dawn. 

Wear it with a knee-length white skirt (poodle optional) to channel a bygone era, or focus on something a bit more futuristic. A crochet mini or a mini with feather trim will accentuate the bold style of this shoe, contribute even more texture to the skirt outfit, and catch the attention of any kind of crowd. 


Heels are always an eye-catching option when paired with a skirt. They naturally accentuate the lines of your legs, helping you look long, strong, and tall, regardless of your actual height. 

We know that you’ve got places to go, people to see, and important things to accomplish, so we’ve selected heels that are comfortable and designed with stability in mind. Of course, we’d never ask you to sacrifice style for substance (or vice-versa), so we’ve made sure each choice is as fabulous as it is functional.

4. Cork-Soled Strappy Sandals

When you step out wearing a pair of cork-soled heeled sandals, you’ll receive compliments from all sides. This style has vintage appeal, but they’ll feel brand-new and are specially designed with your comfort in mind. 

Don’t worry about packing a pair of flip-flops for later—the thickness of the heels on these shoes can lend you comfort all night long. Style these shoes for daytime outings that extend long into the evening:

  • Rendezvous with friends for brunch, visit a museum, then meet a special someone for date night, all in the same outfit. Wearing these strappy heels, a wrap skirt, and a pair of hidden bike shorts, you’ll be ready to take on the town.
  • What shoe could be better for the wedding season? You can walk up and down the aisle, make a splash at cocktail hour, and dance the night away in a silk slip skirt paired with these comfy cork-soled beauties. 
  • For scorching hot summer days that turn into sultry summer nights, pair these heels with a ruffled, short skirt, a blousy top, and an oversized pair of sunglasses. You’ll traverse from an outdoor concert to drinks beneath the stars looking as fabulous as you feel. 

5. Heels With A Bit of Texture

Sometimes, you need a subtler heel that works as well with the skirts you wear to the office as it does for dinner at your favorite patio restaurant. A pair of cut-out heels are a perfect choice. These shoes are usually available closed-toe or open-toe, so you can choose the silhouette that suits you best. 

Wear them with a tailored linen skirt suit and a pair of tortoiseshell reading glasses for a professional look with a stylish and scholarly air. Alternatively, they’re scorching hot paired with a raw-edge denim skirt and a spaghetti strap top. 

No matter the venue, these high heels will keep you appareled with aplomb.


Wedges and skirts are a match made in shoe heaven. With the right pair of wedges, you can pull off pretty much any skirt outfit under the sun. 

From minis to maxis, a comfortable wedge shoe can suit your skirted style to a T. Let’s explore the wedge styles and what they have to offer.

6. Mules to Make a Statement In

They’re bold, and they’re beautiful—whether you’re looking to make waves or turn heads, a pair of mule wedges can certainly capture attention.

Outfits with wedges are a breeze to put together. Depending on the color you choose, a pair of classic jute wedge mules are an excellent option to suit a variety of skirted looks:

  • A tan-and-black mule wedge is the perfect color combination for an evening jazz show or poetry reading at a coffee shop. Pair your mules with a little black skirt, a fitted top, and a delicate shawl for a look that’s right in the pocket.
  • A mule wedge with a bold woven pattern will pair perfectly with a brightly colored long skirt. A halter top will show some shoulder and keep you as comfy as your wedge shoes while you dance the night away.
  • Stay pretty and powerful in a pair of peony pink mule wedges. Pair them with a pencil skirt and a pinstripe blouse, and sweep your hair away from your face to take on political campaigns and profit meetings with polish.

7. Flirty and Comfortable Ankle-Strap Wedges

There is no better shoe for a flirty occasion than an ankle strap, high-heeled wedge. Comfortable, supportive, and cute, this shoe will carry you from table to table at a speed-dating event, down the boardwalk arm-in-arm with a partner, or across the step and repeat at a reunion.

They’re tall enough to give you a boost and secure enough to traverse cobblestones without worry. Whether you’re the type to wear a funky, belted orange mini skirt or a sleek pleated midi-skirt, these high-heel wedges will adapt to suit your unique taste. 

8. “Best of Both Worlds” Platform Wedges

Look, we love all the shoes on this list, but the platform wedge sandal might just reign supreme. That’s because they check nearly all the boxes on this list:

  • The perfectly proportioned flat platform sole has a small lift in the heel to lengthen your lines without stressing your ankles.
  • The adjustable ankle strap and grippy soles will keep you on your feet regardless of the terrain you’re crossing.
  • The sleek design is often available in many dynamic color options to suit your unique style. 

Wear your wedge platforms with a corduroy mini skirt, a black leather skirt, an updated prairie skirt, a set of skirteralls, or a simple flowy linen skirt. They work with almost anything and can keep up with even the most spirited mover and shaker. 

Elevate Any Outfit With a Pair of TOMS

Finding the right shoes to go with your skirt is about more than just comfort—it’s about having the confidence to step out in the style you love and the support to wear it from dusk to dawn.

Whether you’re a skirt person, a pants person, or a jumpsuit person, TOMS makes shoes for women that will guarantee you stay outfitted flawlessly. From elegant wedges to fun and funky flats, from the office to the beach and everywhere in between, TOMS shoes are built to carry you through the world.

Style your skirt and feel fantastic—TOMS is here to help you make it happen.


Reviewed By Andrew David Stewart

Andrew David Stewart is the Manager of Digital Marketing at TOMS and has been working in the digital marketing and social media world for 6 years. Andrew is a lover of nature and the outdoors, and is passionate about telling stories through digital media.