10 Versatile Ways to Wear a Midi Skirt

A classic is a classic for a reason.

As a girl who grew up attending a religious private school, wearing a skirt below my knees often felt like jab at my fashionable spirit. At the time, the two choices I had were to either dress modestly or get sent to the principal's office. So, of course, I did what I was told. But as I’ve gotten older (and more confident in my personal style), I look back on wearing long skirts with more fondness and appreciation.

Instead of wearing a midi skirt five days a week to appease my teachers, wearing one now typically requires a level of thoughtfulness and intention that I may not have once considered. More importantly, it doesn’t feel forced. Instead, it’s intuitive and I’ve realized that I actually feel a sense of independence when wearing a longer skirt on my own terms.

Take, for example, a look I wore recently: an all-white outfit consisting of a poplin midi skirt with a tube top, socks, and sneakers. I walked around the city feeling confident and empowered in my monochromatic outfit the entire day. It’s amazing how clothes have that kind of power over us, and a midi skirt—as basic as it may seem—does too.

Skirts that hit below the knee and above your ankle are so versatile, not to mention, practical for this last leg of intense summer heat. And as the cold weather months approach, they are a transitional weather piece worth investing in. From styling them with crop tops in the summertime to pairing them with boots in the winter, below are 10 ways to wear midi skirts any time of the year.

With Belts

Adding a simple accessory like a double belt can elevate any outfit, but especially a navy pleated skirt. The chic cropped sweater and collared shirt don’t hurt either. Finish the look with a pair of combat boots and sunglasses for the ultimate rebellion.

With A Moto Jacket

There’s no question that sheer fabrics are what all the It-girls are wearing this summer. With a pair of hot pants or micro mini shorts underneath, you can participate in the trend without worry about coverage. With no shortage of transparent and delicate options on the market, including this nude floral pencil-shape version, you are sure to be the most on-trend woman in the room. And since your transparent skirt will most likely be your outfit’s main focal point, you can try styling it with a simple white T-shirt.

With a Crop Top

One of my favorite ways to wear a midi skirt is with a crop top and heels. This high-waisted A-line silhouette works perfectly for a more elegant occasion. Even with an all-black outfit, the leather material offers a nice contrast. Oh, and don’t forget a pair of statement earrings and sunglasses.

As A Skirt Suit

If there’s one internet trend that has boomed this year, it's corpcore. And this two-piece tailored skirt set is the type of outfit that is right on par with this trend. The blazer, which in this case is being worn more like a top, features a peplum style bodice creating a waist-cinching effect. Layered underneath is a matching pencil skirt that hits just above the ankles. This hem length allows for your shoes to be on full display, so make sure you choose your footwear wisely.

With Strappy Sandals

A great piece to wear during the summer season is a flowy ivory midi skirt. One way to get the look is to pair your midi with a black contrasting square neck tank top, but it’s the accessories that make the big difference here. Adding a little dainty black belt over your waist is an easy way to add dimension to an otherwise plain look. A good oversized hobo bag can add visual interest where it counts. Lastly, any strappy sandal will have you looking polished and effortless.

With a Hoodie

Midi skirts can feel way too dressy at times, but adding an athleisure element can help make them more casual. All you need is a gray zip-up hoodie, a black skirt, and a pair of white sneakers. So next time you reach for your sweatpants, try a midi skirt-and-hoodie combo instead. I promise you’ll be comfortable but put together.

With Loafers and Socks

The only thing that separates this incredible street style look from a private school uniform is the fact that her crisp white button down isn’t tucked into her pleated skirt. This relaxed and casual take on the classic necktie is one that's versatile and easy to pull off. The loafers and white ankle socks are the final touch that make this outfit a masterclass in academia dressing.

With a Graphic Tee

A short sleeved graphic T-shirt might be one of the easiest ways to style any midi skirt. You can either lean into being more casual with sneakers or you can wear a heel to slightly dress it up. A light and airy skirt will flow so well with your tee, even better if it's styled with a woven basket bag to really play up the summer vibe.

As a Canadian Tuxedo

Trust me when I say that denim on denim is always a good idea. The elements in this outfit—a thin black belt, sunglasses, and a shoulder bag—have an effortless yet sophisticated allure. To up the fun factor, add a pair of mules in a vibrant print.

With a Strapless Top

A midi skirt can transition from a day to night with a few simple styling choices. Here you have a navy pleated skirt worn with a white going out top perfect for a dinner date or drinks with the girls. The juxtaposition between a modest looking skirt and a more revealing top makes this otherwise basic outfit more interesting. Paired with mules and a matching shoulder bag, this midi skirt will have you ready for a night out on the town.

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