Pleated skirts are back—and not just in a “prep rally at 3 o’clock” kind of way. Whether it’s a knife-pleated midi, a crisp A-line mini, or a flowy chiffon maxi, today’s pleated skirts are chic, versatile, and totally grown-up—if you style them right. The fastest way to ruin the look? Pairing them with the wrong shoes and accidentally slipping into “freshman year flashback” mode.
But don’t worry—we’re not here for that. We’re here for pleats with power, polish, and a bit of edge. Below, we’ve rounded up 7 shoes that complement pleated skirts beautifully in 2025, helping you stay modern, stylish, and miles away from anything that resembles a school uniform.
1. Slingback Kitten Heels
Picture a sophisticated evening out; slingback kitten heels are your go-to. They add an elegant touch while elongating the leg just enough. A modern edge is achieved with soft neutrals, mesh details, or a hint of metallic.
Ideal for transitioning from the office to a dinner date, these heels manage to be both chic and versatile. They complement minimalistic looks effortlessly, allowing your pleated skirt to take center stage without overpowering it. These heels whisper elegance, making them perfect for anyone looking to make a subtle yet impactful statement.
2. Chunky Loafers
Chunky loafers are making waves in the fashion scene of 2025, offering a fresh twist to the classic preppy style. With a platform or lug sole, they bring weight and a cool contrast to the softness of pleated skirts. These loafers excel in balancing textures, especially when paired with structured blazers or oversized knits.
They exude a confident vibe, perfect for those who appreciate a blend of tradition and modernity. Ideal for a day of urban exploration or a casual lunch meeting. Their bold presence ensures you’ll stand out in any crowd.
3. Sleek Boots
For those transitioning between seasons, sleek boots are a must-have. Whether crafted from leather or suede, these boots add polish to any ensemble. The pointed or square toe offers a modern silhouette that pairs seamlessly with midi-length pleated skirts.
Perfect for fall or spring, they work well with tights or bare legs, adapting to various climates. These boots bring sophistication and versatility to your wardrobe, making them a staple for any transitional outfit. They capture the essence of contemporary style, ensuring you’re always prepared for shifting seasons.
4. Minimalist Leather Sneakers
Embrace a casual yet stylish look with minimalist leather sneakers. These shoes embody effortless cool with their slim profile and classic white or off-white hues. Brands like Veja, Axel Arigato, or Common Projects offer designs that exude sophistication without appearing juvenile.
Ideal for weekend outings, street style, or travel, they provide comfort and a laid-back vibe. These sneakers complement pleated skirts beautifully, ensuring you stay fashion-forward without compromising on comfort. Perfect for those who appreciate simplicity and elegance in their everyday ensemble.
5. Strappy Heeled Sandals
Strappy heeled sandals take your pleated skirt from casual to chic with ease. Opt for designs in earthy tones or metallics to add an elevated touch without overpowering your outfit. These sandals are perfect for summer weddings, date nights, or rooftop cocktails, offering a dressed-up vibe.
Their intricate straps provide a delicate aesthetic that complements the fluidity of pleated skirts. These sandals ensure you step out with confidence and flair, capturing attention with their understated elegance. Their versatility makes them a cherished addition to any wardrobe.
6. Ballet Flats with a Twist
Ballet flats have evolved, shedding their ‘precious’ reputation with modern updates. Features like square toes, mesh fabrics, or sculptural details keep them fresh and exciting. Ideal for feminine and romantic looks, they pair seamlessly with pleated skirts.
Whether you’re strolling through a Parisian market or attending a garden party, these flats offer comfort and style. They exude charm without veering into costume territory, maintaining a balance between tradition and modern flair. Perfect for those who value subtle elegance in their footwear choices.
7. Western-Inspired Short Boots
Urban cowgirl meets editorial chic with western-inspired short boots. These boots create an unexpected contrast when paired with pleated skirts, offering a fashion-forward option for transitional weather. Embroidered details or unique stitching add character, making them standout pieces in any outfit.
Perfect for those who love pushing fashion boundaries, these boots are ideal for daytime adventures or casual outings. They encapsulate a blend of rugged charm and contemporary style, ensuring you’re always at the forefront of fashion trends. Embrace the microtrend with confidence and flair.