9 Plaid Skirt Outfits We’re Trying Out This Season

Whether your style leans polished, romantic, edgy, or somewhere in between, there’s a plaid-skirt outfit worth adding to your mood board ahead. Keep scrolling for the chicest ways to wear the enduring print this season, from casual daytime looks to holiday-ready ensembles you’ll want to copy immediately.

Ruffled Blouse + Plaid Skirt + Ballet Flats

A pleated plaid skirt may nod to prep-school dressing, but styled with a rich chocolate-brown sweater and sleek slingback pumps, it feels decidedly grown-up. The tonal palette gives the look a polished, elevated feel, while the mini silhouette keeps it playful and date-night ready. Add a structured bag to complete the outfit, and you’re set for everything from dinner reservations to a cozy evening spent wine tasting.

Play with proportion this season by pairing a plaid pleated maxi skirt with a cropped trench and a barely-there top. While plaid skirts are often shorter and trenches traditionally longer, this combination flips the expected silhouette in a way that feels especially fashion-forward. Finish the look with chunky-heeled knee-high boots for an outfit that’s equal parts heritage-inspired, cool-girl, and just a touch punk.

A playful plaid skort delivers the look of a mini skirt, while the built-in shorts make it a practical pick for everything from pumpkin picking and leaf-peeping to cider tasting and weekend road trips. Styled with a cozy ribbed cardigan and suede knee-high boots, it strikes that coveted balance between comfortable, polished, and effortlessly seasonal.

A high-low silhouette, ruffled hem, and soft ivory plaid print give this look an effortless rustic charm that’s perfect for fall. The flowing skirt feels a little bit Western-inspired and a little bit romantic, making it an easy choice for everything from a vineyard visit to pumpkin picking or a day spent wandering a local fall festival. Paired with a creamy knit sweater and suede knee-high boots, the mix of cozy textures feels rich, elevated, and undeniably seasonal.

Off-the-Shoulder Top + Plaid Skort + Tall Boots

Fall date-night dressing can feel like a balancing act, but this outfit makes it look effortless. The off-the-shoulder top adds a flirty touch, while the plaid skort keeps the look playful and on-trend. Finished with suede knee-high boots, it strikes that perfect mix of coverage and skin-baring detail that’s ideal for crisp autumn evenings. Equal parts polished and romantic, it’s an outfit you’ll reach for whether you’re heading to dinner, drinks, or a spontaneous girls’ night out.

Turtleneck Sweater + Ruffled Plaid Midi Skirt + Suede Boots

If there’s one styling trick that never fails this time of year, it’s leaning into texture. A chunky ivory turtleneck, a plaid ruffled skirt, and rich suede boots create the kind of outfit that feels quintessentially autumnal in the chicest way possible.. The result is undeniably classic with just enough personality to stand out, whether you’re heading to a cozy weekend getaway, hosting Thanksgiving, or spending the afternoon at a holiday market.

Ruffled Cardigan + Plaid Mini Skirt + Knee-High Boots

A cardigan and plaid mini skirt are about as timeless as fall dressing gets, but thoughtful details make this version feel especially current. The ruffled trim adds a feminine, fashion-forward touch, while the neutral taupe palette keeps the look feeling elevated and versatile. Finished with rich chocolate leather knee-high boots, the outfit strikes the perfect balance between polished and playful. Whether you’re headed to brunch, browsing a farmers market, or meeting friends for a casual dinner, it’s an outfit formula you’ll come back to all season long.

We want to see your plaid skirt outfits! Show us on Instagram or TikTok @lulus using #lovelulus and head to our Fall Fashion Shop for more must-have seasonal styles!

This post was originally published in 2021 and has been updated with new content.