Mona May, the costume designer on Clueless, told Vogue that she wanted Cher's famous yellow suit in plaid because it was "the quintessential schoolgirl outfit." She tried red and blue first, and only the yellow worked. Thirty years later that suit is still the first thing most people picture when you say plaid skirt, and I think it explains the appeal: plaid is a uniform pattern, so wearing it on purpose always feels a little knowing.

 

This first group is the classic end, wool and tweed and the checks you would find on a kilt or a country jacket. Weekend Max Mara's Wkdprisma is a stretch wool twill wrap, the one I would wear to an office. Barbour's Hazelwood is pieced from two country checks, from a brand that has been making outerwear since 1894. Ralph Lauren's plaid tweed skirt has a fitted yoke and a very traditional look. Favorite Daughter's Meyer is a straight skirt with a front slit, and Posse's Pippa is a bold black and white check column. Lioness's Play On is a small chocolate check that sits just below the knee, Joe's Jeans' Ines is brown plaid cut on the bias, and All The Ways' Betty is dark navy plaid with a handkerchief hem.

 

My test with plaid is to look at the side seam. On a well made skirt, the lines meet across the seam. If they jump, every outfit will look slightly off.

 

What I would skip: a plaid skirt with a plaid shirt, unless you are going to a costume party as Cher.

A bias cut or a slip skirt makes plaid move, and that changes it completely. The pattern stops looking like a uniform and starts looking soft.

 

Aya Muse's Kae is the most fluid skirt here. Lovers and Friends' Cassandra and Tularosa's Margo are both easy midis, and Vince's Diamond Plaid slip skirt sets the check on the diagonal so the lines run like a harlequin. ALIGNE's Yvonne is a long check maxi in brown and green, and Yuhan Wang's maxi is blue and white with a lace trim. Hunter's handkerchief skirt has a pointed hem that swings, and Gestuz's Aleya sits high on the waist.

 

A pairing tip: a bias plaid skirt wants a fitted knit on top, something fine and close to the body, so the movement stays in the skirt.

 

What I would skip: a stiff jacket that covers the hip. You lose the drape you picked the skirt for.

This third group plays with the shape of the skirt itself: sheer layers, drapes and uneven hems.

 

Bec + Bridge's Eliana is the most daring, sheer with a high slit, and Lioness's Shoreline layers sheer plaid over a slip. Frame's Plaid Organza skirt is sheer, so the pattern floats over the leg. Lovers and Friends offers two here, the Lucielle and the Cassidy, both with a little more drama in the cut. RÓHE's Draped Check skirt is the most considered, and rag & bone's Wren is a pale plaid on the bias. LPA's Velora is a sheer brown plaid with a handkerchief hem that falls into long points.

 

A pairing tip: with a draped or asymmetric skirt, keep the top short or tucked so the line of the drape shows from the waist down.

 

What I would skip: a tall boot with the organza skirt. The sheer fabric catches on the shaft, so wear it with a low shoe or a bare leg.

The last group is where designers treat plaid as a print rather than a uniform, so the colours get brighter and the cuts get stranger.

 

Miu Miu's checked wool blend is the loudest, a red, green and yellow check set on the diagonal, and Carolina Herrera's checked pencil is pink, green and white and the one I would wear to a meeting. Gabriela Hearst's Wesley is a brown wool and silk check with pleats at the hem, the most grown-up skirt in the edit. Bottega Veneta's checked cotton is white with a faint windowpane and a hem cut into points, and Rosie Assoulin's space-dyed silk column has a check so soft it almost reads as a stripe.

 

For less money, SIEDRÉS' Colette is a light checked georgette in peach and blue, Chorus' Leandra is a dark green plaid with a wrap draped across the front, and Vince's ombré slip runs a small check from black down to camel.

 

A pairing tip: with a bright or unusual check, pull out one colour from the skirt and wear it once on top, in a plain knit.

 

What I would skip: a patterned bag. The skirt is already doing the talking.

Plaid comes back every autumn because it is a pattern with a story, from the tartans of Scotland to the punk version Vivienne Westwood made her own and the yellow suit in Clueless. I like a plaid skirt best when it is worn with plain things and a little confidence.

 

If I were buying one, I would choose a wool or tweed midi from the first group, Weekend Max Mara or Barbour, because a classic check works with a knit, a shirt or a leather jacket for years. The bias and slip skirts are for someone who wants plaid to feel soft, and the designer checks are for someone who wants it to feel new. Whichever you choose, check that the lines meet at the seams. If you want to keep browsing, I also put together Best Midi Skirts and Why are Midi Skirts So In.