My Ultimate Guide to Wearing Midi Skirts with Any Shoe

By: Emily Whitehill.

Published on

- 4 min read

Midi skirts have made a grand comeback and for good reason. They are versatile, chic, and can easily transition from day to night with the right styling. But, the question that often stumps many is: What shoes do I wear with a midi skirt? Fear not, for I’ve got you covered with my ultimate guide to wearing midi skirts with any shoe. Let’s dive in.

 A full-length image of a young woman with wavy brunette hair, wearing a floral midi skirt and white sneakers, standing on a city street, afternoon.

Sneakers: The Casual Go-To

Starting with the most casual and comfortable option - sneakers. Pairing your midi skirt with sneakers not only screams comfort but also adds a cool, laid-back vibe to your outfit. It’s perfect for those days when you’re on the go but still want to look put together. Whether you opt for a plain white tee or a cozy sweater, sneakers can make any midi skirt look effortlessly chic.

Sneakers work particularly well with flowy or A-line midi skirts. The contrast between the skirt’s femininity and the sneakers’ casualness creates a balanced and modern look. Remember, the key is to keep your sneakers clean and simple. Too much detail or color can overwhelm the outfit.

Boots: For the Edgy and Chic

Boots and midi skirts are a match made in fashion heaven. Whether you’re leaning towards ankle boots, knee-highs, or even over-the-knee boots, they can all work wonderfully with midi skirts. Boots add an edgy touch to the softness of the skirt, creating a dynamic and interesting look.

 A full-length image of a young woman with short blonde hair, wearing a pleated midi skirt, black leather ankle boots, and a denim jacket, urban setting, evening.

When wearing boots with a midi skirt, pay attention to proportions. Ankle boots are great for creating the illusion of longer legs, especially when paired with a skirt that ends just above or at the mid-calf. For a bolder statement, over-the-knee boots paired with a shorter midi skirt can create a stunning and chic ensemble.

Heels: Elevate Your Style

Heels are the go-to option when you want to elevate your midi skirt look. They add height, elongate your legs, and bring an element of sophistication to your outfit. Whether you’re attending a formal event or heading out for a dinner date, heels can transform your midi skirt from casual to elegant in an instant.

 A full-length image of a young woman with curly red hair, wearing a satin midi skirt, strappy heels, and a silk blouse, cityscape background, sunset.

Stilettos, block heels, or even kitten heels work beautifully with midi skirts. The key is to choose a heel that complements the style of your skirt. For instance, a sleek stiletto pairs well with a fitted midi skirt, while block heels are great with fuller skirts for added stability and comfort.

Flats: Comfort Meets Style

Flats are the perfect blend of comfort and style. They’re ideal for those days when you’re not feeling heels but still want to look polished and put-together. Ballet flats, pointed-toe flats, or even loafers can add a sophisticated touch to your midi skirt without compromising on comfort.

 A full-length image of a young woman with dark hair in a bun, wearing a chiffon midi skirt, pointed-toe flats, and a blazer, bustling city background, morning.

Flats work best with midi skirts that sit at or just below the knee. This ensures that your legs don’t appear shorter, which can sometimes happen with midi lengths. Pairing your midi skirt with flats is also a great way to achieve a business casual look that’s both stylish and office-appropriate.

Sandals: The Summer Staple

As the weather warms up, sandals become the go-to shoe choice for many. They’re airy, comfortable, and can add a laid-back or elegant touch to your midi skirt, depending on the style you choose. From gladiator sandals to sleek slides, the options are endless.

 A full-length image of a young woman with sun-kissed skin, wearing a lightweight midi skirt, strappy sandals, and a crop top, urban park setting, bright sunny day.

Sandals are perfect for creating a summer-ready look that’s both comfortable and chic. Pair your midi skirt with flat sandals for a casual daytime outfit or opt for heeled sandals for a more dressed-up look. The key is to let your skirt be the star of the show, with the sandals playing a supporting role.


Midi skirts are incredibly versatile and can be styled with a wide range of shoes, depending on the occasion and your personal style. Whether you prefer the comfort of sneakers and flats, the edgy look of boots, the elegance of heels, or the laid-back vibe of sandals, there’s a way to make midi skirts work for you. Remember, the key to nailing the look is to pay attention to proportions and choose shoes that complement your skirt and overall outfit. With these tips, you’ll be able to rock midi skirts with any shoe in your wardrobe.