Dallas fashion blogger Ashley Nudge wearing a monochromatic midi skirt look with a burgundy moto jacket

How to Style a Midi Skirt (Without Looking Like a Grandma)

One of the top trends from the Fall/Winter 2017 runways is the midi skirt. Slightly longer than a knee-length skirt, a midi skirt is a one that ends at the middle of the calf. As the weather gets colder, a midi skirt is perfect for days when you don’t want to wear a mini skirt and tights, but still need to bundle up down below. This style of skirt is also great to include in your wardrobe, because the silhouette is timeless, sophisticated, and comfortable. An A-line midi skirt is ideal for creating a ladylike, hourglass shape that hints at 1950’s glamour.

Since the midi skirt hem is longer than other skirt hems, it’s common for people to shy away from midi skirts. Wear one incorrectly, and it’s easy to come off as looking like a grandma! Today, I’m conquering your misconceptions of midi skirts by breaking down 3 ways to wear them this fall. My hope is that you’ll give second glance to midi skirts while shopping online or in stores. Style one based off these tips, and you’ll realize midi skirts aren’t that bad! 🙂

Keep scrolling to find out how to style a midi skirt, without looking like a grandma!


For a high fashion-inspired outfit that exudes elegance, build a monochromatic look around your midi skirt. Start with a maroon striped tank top, and tuck it into a midi skirt in a similar color. This tank top is only $20, and I love little ruffles and feminine bow detail on the neckline! Push the color scheme to the limits by throwing on a burgundy moto jacket for warmth. The removable, white fur collar on this jacket makes it look expensive and luxurious, but it’s under $45! Lastly, the key to looking less grandma-like in a midi skirt is to wear heels instead of flats. Step into a pair of wine-colored leather booties to tie the look together. These booties have a patent-leather detail on the toe, and are extra chic for fall!


Target Shirt, Target Jacket, Metro Wear Skirt (similar), 1969 Italia Shoes (similar), J.Crew Factory Earrings (similar), Bracelet (not sure), REVLON Lipstick in ‘Plum Velour’


The next way to style a midi skirt is by mixing prints. Doing so could look grandma-ish if you mix floral prints and don’t tuck in the top. So, instead of florals, opt for an unexpected combo of leopard print and plaid. This green leopard-print sweater is thin enough for layering, and the black spots give it an edge. Tucked into this black and white plaid midi skirt, you have a classy look that is equal parts fun and sophisticated! Put on some over-the-knee leather boots to keep it youthful and a little sexy. 😉


Target Sweater, NY Collection Skirt, Studio Paolo Boots (similar), Vintage Earrings, Vintage Belt (similar), REVLON Lipstick in ‘Plum Velour’


The last way to style a midi skirt (without looking like a grandma) is by layering it over a gingham-print midi dress. Gingham was a huge trend over the summer. So layering a black pleated midi skirt on top of gingham pieces is an ideal way to transition them to fall! This dress has off-the-shoulder sleeves, but I only wore one sleeve to create a unique, one-shoulder style. I also took the waist-tie off and wore it as a necktie instead! Give the look some rocker vibes with black sock booties, a concho belt, and gold fringe earrings. I call this look my “Pirate Girl Chic” look, because it looks kind-of pirate-y! Perfect for Halloween season! Why not?!



Olivia & Grace Dress, NY Collection Skirt, BCBGeneration Booties (similar), ALDO Choker Necklace (worn as bracelet – similar) Thrifted Belt (similar), Earrings (not sure – similar)

To wrap up this post, I want to say a special thank you to Greg Daniels for photographing these looks. Greg is honestly the most talented fashion photographer in Dallas, and we had a blast experimenting with these editorial concepts. Let me know what you think of them in the comments, along with which look was your favorite! 😀

Click here for more fashion editorials exclusive to The Ashley Edit!




Photography: Greg Daniels


  • Reply Monday Link List: Six Blogs to Read This Week - LATTES + LONGLINES October 23, 2017 at 8:17 am

    […] Ashley of The Ashley Edit shows you how to style a midi skirt! […]

    • Reply Ashley October 23, 2017 at 11:35 pm

      Thanks for reading, and for the feature! Much appreciated!

  • Reply Yoanna Kalova November 9, 2017 at 3:55 am

    Great article and pictures! I think midi skirts are a good choice if a woman wants to look feminine, romantic and serious at the same time. I like them very much. You have given us great tips on how to match them with other clothes. Thanks a lot!

    • Reply Ashley November 9, 2017 at 3:45 pm

      Hi Yoanna!

      Thanks for checking out this post. I’m so glad you found the tips useful!



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