At some point over the past year, we found yet another nostalgic item sneaking its way back into our wardrobe. Plaid skirts — both of the short, pleated variety and long, flowy designs — were popping up everywhere, inspiring us to get a little preppy. With social media as our guide, we felt an urge to style them with socks, loafers, and sweaters, creating looks that nailed both the schoolcore and light academia trends.

Now, as fall rolls around once again, we're itching to try even more plaid skirt outfit ideas. Unsurprisingly, there's a ton of inspiration out there, since this piece is extremely versatile. Whether you're someone who enjoys the classics or are down for experimenting with new ways to wear old things, you'll find a ton of looks worth giving try, ahead.

The Schoolcore Way

Add a T-shirt, scrunched-up socks, and a pair of sneakers or loafers and you've nailed the look.

With a Blazer

It's a sleek layering choice, but a pair of boots and chain necklaces will keep your look from feeling too corporate.


Go ahead and throw on that graphic tee, a camo jacket, and combat boots for a fun punk combination.

As Part of a Set

You can even spice up a suit by adding a plaid button-down in a similar colorway, testing out fall 2021's 3-piece outfit trend.

With a Turtleneck

When in doubt, this simple shirt option looks cute every time.

With a Graphic Top

If your plaid skirt is structured, this styling choice will help make it more casual and laid-back.

With a Polo

Two traditionally preppy pieces make for the perfect pairing.

Mixing Prints

While plaid skirts tend to feel classic and traditional, throwing on an extra print will transform your look into something unexpected and playful.

Complete With Some Sneakers

The more outrageous and colorful, the better.


Even if it's not exact match, styling your skirt with a top, shoes, and accessories within the same or similar color families will create an outfit that really stands out.


Get out of your comfort zone and combine pieces that feel like opposites. It's a trick that Patricia Field relies on when dreaming up iconic outfits for both Carrie Bradshaw and Emily in Paris.

With a Sweatshirt

Even if you're trading your jeans and joggers for a plaid skirt, you don't have to ditch all your comfy clothes. This baby pairs perfectly with solid hoodies and chunky boots, too.

With a Vest

Styled For Chilly Days

A plaid maxi skirt will act like a blanket for your legs, while longer-length boots provide some extra warmth. Complete the look with a leather jacket.

Layered Over Pants

Yes, this Y2K trend is back and there's no better time to experiment.

Paired With Standout Pieces

A leather blazer, fluffy slipper shoes — it's adding statement pieces like these that will help a plaid skirt and T-shirt combo really pop.

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