
Skirt season doesn’t end when the cold weather arrives–but you knew that already! The closet staple can be worn all year round and makes the perfect addition to all of your cutest looks, especially when it comes in plaid. And there’s no better time to play with classic pattern than fall and winter: Plaid skirt outfits are timeless, versatile, and totally appropriate for all of your festive-season activities.

Plaid skirts are a classic back-to-school item, but you don’t have to be going back to school to rock this look. While you’ll see a lot of them appear in the fall, these wardrobe staples can easily be worn during any season. Despite the ‘loud’ pattern, plaid skirts are versatile and can be styled to suit any occasion, aesthetic, or trend. They’ve really never gone out of style, and each generation has created new and trendy ways to wear them.

Whether your vibe is edgy, trendy, romantic, or a little bit of each, you’ll find outfits worth copying–and shopping–ahead. Get ready to rock those chilly days and cozy holiday nights in style with our guide on what to wear with a plaid skirt.
’90s Vibes

The ‘90s were all about grunge–dark colors, fringed edges were in, and everyone was wearing Doc Martens. Moody and cute, this look would be perfect for a day of reading at a coffee shop, shopping with friends, or celebrating a special occasion.
That ’70s Babe

If the ‘90s aren’t your vibe, maybe the ‘70s are! This cute outfit gives vintage vibes while still feeling current and on trend. We love the look of the loose sleeves on this slouchy sweater, and the round retro sunglasses are the cherry on top of this outfit.
Chic and Sophisticated

Apple picking, going to a local harvest festival, enjoying a warm coffee with our friends–these are just a few things we can imagine doing in this outfit! Particularly autumnal, the warm brown tones combined with cream and gold feel almost like a pumpkin spice latte. The long-sleeve top will keep you warm if you’re enjoying an outdoor activity, but this would also be a sweet outfit for a family holiday get-together.
Mint Condition

Evergreen looks fresh for fall–especially when paired with creamy neutrals. For a more casual occasion, style the skirt with neutral white items like a simple white bodysuit and a crossbody bag. Add a pair of western boots and a wide-brim hat, however, and you’ve got the perfect look for a brunch date or a backyard BBQ party.
Everything is Black and White

‘Tis the season for luxe-looking fashion! As much as we adore warm, rich tones for fall and winter, there’s nothing quite like a timeless black and white look. Textured fabrics like suede, ribbed knits, woven leather, and wool-blend flannel keep the classic color combo from being boring–as do polished gold accents. This sexy, graphic outfit (with a hint of equestrian vibes) is perfect for a first date or a night out on the town.
Preppy and Polished

If you love the back-to-school style vibe but you’re wearing more elevated looks now, this adorable but sophisticated look should check all the boxes. Comfortable-but-still-cute ankle booties, a chic crossbody, and gold accessories tie together the preppy vibes, but you’ll definitely feel more like a (stylish) teacher than a student when you wear this look.
The combination of navy and cream in the plaid skirt is traditional and classic, but the pop of warm coral takes the pattern to the next level.
Edgy-Girl Autumn

If you love classic fall fashion but it isn’t quite baddie enough for your taste, this look might just be your cup of tea. Sneakers keep this look down to earth, but the rest of this fit is anything but. If you’re a fan of Clueless, this look might remind you of something Cher or Dionne might wear, especially the leather bucket hat!
Think Pink Plaid

Dainty and soft, this plaid look feels sophisticated and festive, the perfect outfit for enjoying a fancy brunch, celebrating with family, or even for an important day at work. The soft grey, peachy nude, and pink tones in this outfit all work so well together, creating a dynamic but cohesive final look.
Pretty Sweet

Meeting your SO’s family for the first time this holiday? First impressions are everything, so you’ll want a look that’s fashion-forward and approachable. Pair a classic plaid skirt with a romantic neutral top, then finish the look with suede boots and a polished clutch. The colors are perfect for the season, and you’ll be winning them over in no time.
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.
Join The Conversation (2)
Pretty 😍
Definitely going on my outfit wishlist
Yes! We love it!
xo