A pleated midi skirt is a classic piece, and they’re not just for dressing up anymore. Casual pleated midi skirt outfits are trendy these days, and they’re some of my personal favorites to style because you can go with everything from a graphic tee and sneakers to sandals and a tee. Whether you’re looking for an office-friendly outfit with a pleated skirt or a black pleated midi skirt outfit to wear this winter, it’s such a versatile piece that can go incredibly far in your closet. And since my love for pleated skirts has grown so much in recent years, today I’m sharing 8 pleated skirt outfit ideas to show you how to transition your skirts from season to season, featuring some of my favorite pleated skirts in my closet!
Fall and Winter Pleated Midi Skirt Outfits
Arguably, the easiest way to style a pleated midi skirt is for fall or winter. The length, drape, materials (think satin and faux leather), and colors (black, brown, jewel tones, and patterns like leopard print and houndstooth) are perfect for the chillier months. One of the most classic ways to wear a pleated skirt when it’s cold out is with a sweater. From here, you can dress it up or dress it down—add a belt and heeled booties for the office, do a simple sweater tuck and add sneakers for a casual look, or find a cropped, slightly boxy sweater to create a cozy casual outfit with ankle boots. I also love pairing my satin midi skirts with a long sleeve turtleneck bodysuit for a pleated midi skirt outfit that’s hassle-free for date night, like I did with the black pleated skirt below. In the winter, a cropped or mid-length faux fur jacket or tailored camel coat is a great way to add extra warmth while keeping the look proportional.
Summer and Spring Pleated Midi Skirt Outfits
Spring and summer might not be the most intuitive seasons for a pleated midi skirt, but it can be an easy alternative when you’re tired of shorts and dresses. My go-to way to wear a pleated skirt in the summer is with a t-shirt tucked in or knotted in the front, or I’ll make things totally seamless with a sleeveless bodysuit. You could also pair a cotton button up (tied in the front), but whichever top you choose, it will look great with sandals, flats, heeled mules, or white sneakers. To finish a pleated skirt look in the warmer months, I usually grab a straw bag and a denim jacket to beat the A/C indoors or for brisk evenings. In springtime, I love layering a long trench coat over top. For an easy pleated skirt date night look, tuck in a lace top and grab your favorite neutral leather jacket and high heels.
Featured Pleated Midi Skirts
Below, I linked a few of the midi pleated skirts I own as well as in-season pleated skirts to browse. A few of my favorite retailers to shop for pleated skirts are J.Crew, Banana Republic, Anthropologie, H&M, Zara, and Mango. The ladder three release at least one gorgeous affordable pleated midi every single season, and they’re usually under $50 and in the most beautiful greens, blues, and browns.
Just a note—pay special attention to the closure style (pull-on, zipper, etc.) as this will affect how the skirt lays against your waist. Also, I recommend opting for pleated skirts in a length that hits mid-calf, as anything shorter or longer can limit the styles of shoes you can wear with it. If you opt for a long skirt to wear with knee-high boots in winter (one of my favorite chic pairings), just be sure to account for the height of the shoes when considering length or budget for a visit to the tailor.