The plaid skirt has had many wonderful fashion phases, from 1980s punks to 1990s ‘Clueless’ costumes. The plaid skirt can now be found in many forms in mainstream and high-end stores. Pencil midi skirts, pleated maxis, and pastel hues ahoy. 

Here are our favorite plaid skirt outfits for your inspiration! 

Brooke Shields’ matching skirt suit, sheer stockings, and pumps 

Check out Brooke in her lemon yellow plaid skirt suit! An upstanding member of society with demure stockings, simple heels, and large, round earrings (most likely clip-on). Bring back the pencil skirt and blazer duo. 

1980s Punk with Leather, Ripped Tights, and Lace-Ups 

The plaid skirt is synonymous with 1980s punk, worn with ripped stockings, studded leather jackets, and lace-up Doc Martens. Accessorize with a silver chain around the hips and multiple silver chain necklaces. Mohawk optional. 

Suspender Skirts and Ruffled Blouses

Get in the 1960s spirit and find an a-line plaid skirt with suspenders and a high waist. Layer over a white shirt with lace front ruffles and puffy sleeves. To edge this baby up, add studded ankle boots and a slouchy trench coat. 

A Tight, Cropped Sweater and Pleated Plaid Mini  

Go full 90s and pull a Mariah with a plaid mini, cropped and fitted cardigan, stockings, and heeled brogues. Wear your teeny tiny cardigan over a plain white tee, and accessorize with nothing but dark sunglasses. 

Matchy-Matchy Mini and Shirt 

Scour the market for a matching plaid mini skirt and shirt combo. If you’re a whiz on the sewing machine, get a bunch of bright plaid fabric and create your own custom set! Pair with thigh-high suede boots and head out for an all-nighter (why waste an outfit as rad as this?). 

Generous Volume, a Fitted Cardi, and Slouchy Boots  

Take inspiration from Princess Kate and pick a pleated plaid maxi that flares and moves as you walk. Pair your statement skirt with a fitted cardigan buttoned all the way to the neck (demure, darling!). Add slouchy heeled boots and minimal accessories, such as a solo bangle or gigantic diamond ring (or cubic zirconia).

Lacy Design Details and Roomy Tee 

DIY your pleated midi-skirt by adding lace or contrast-tone fabric inserts at the hip. Pair with a relaxed-fit tee, a cute handbag, and gnarly lace-up shoes or boots. 

Maxi Skirt, Cropped Leather, and Layered Necklaces 

The mini may be what you first think of when you hear “plaid skirt”, but the maxi is just as charming. Pair an a-line maxi skirt with a fitted black crop, a cropped leather jacket, and platform lace-ups. 

A Sleek Midi, Chambray Shirt, and Statement Heels 

The ever-reliable chambray shirt is the perfect match for a plaid midi skirt. Tuck it in, shimmy it on out for a blouson effect, and roll the sleeves up like you’re about to check the oil. Add statement mules and a contrast-tone handbag for pre-show fashion week street style. 

Classing Patterns

Get playful with your prints by pairing a plaid midi with a striped, ripped sweater. Or, try polka-dots and plaid, or florals and plaid, there are no limits. Take it a step further by adding texture and color with statement flats, heels, or boots. 

Monochrome, Roomy Sweatshirts, and Slimline Midi Skirts 

Build a monochrome look around the hue of your slim-line plaid skirt. Tuck an oversized sweatshirt into your high waistband, and add a matching clutch and strappy heels to follow the color story. A ¾-length plaid skirt with a sleek silhouette works like magic. 

Graphic Tee, Stacked Sneakers, and a Puffer Coat 

Add further color and pattern to a bold-toned midi-skirt with a graphic tee, multi-hue brogues, and a puffer coat. Accessorize with cool-toned jewelry such as layered silver necklaces or white gold hoops. Embrace the miss-match of color, texture, and print. In fact…push it as far as you can. 

A Sweater Around the Waist, Plain White Tee, and Chunky Heels 

Style your plaid pencil skirt Hey Arnold-style by tying a contrast-pattern sweater around your waist. (For authentic Arnold, tie a plaid shirt…O.G fans understand!). Add a crisp white tee and chunky statement heels or boots. 

Thigh-High Boots, a Beret, and Simple Sweater 

Pair a ruffle-hem plaid mini with thigh-high boots in soft suede. Tuck a simple, relaxed-fit sweater or long-sleeved tee into your skirt, pop a jaunty beret on your head, and stroll out for a pastry. Accessorize with a basket-style tote and dark sunglasses for market strolling. 

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