Every season there are new trends that make me scratch my head.  I expect this.  However, when I saw plaid midi skirts back in the stores again I had to wonder what in the fresh hell anyone was thinking.  Does anyone want to look like they are ringing a school bell in 1982?  Can you get any more frumpy and matronly than a plaid midi skirt?

I started studying the trend’s return to try to make some sense of it.  I couldn’t wrap my brain around who exactly, besides the Queen of England, would lean into the plaid midi skirt’s resurrection.   I started to notice that it’s not the plaid midi skirt itself that is making a comeback but how it is worked with more updated pieces to make it look cool, in an awkward, mixing of trends, sort of way.  It’s definitely being targeted towards the young, not those who remember it the last time it was popular.  I can’t say that this made me a plaid midi skirt convert, but it did help me understand why it’s back.

Five Ways to Wear a Plaid Midi Skirt

If you are also scratching your head wondering who on earth would wear a plaid midi skirt, check out these five looks I put together with this Lafayette 148 plaid midi to get some ideas of how designers are envisioning it being styled.  At this end of the post, if you are feeling like you actually want to try out a plaid midi skirt, check out more styles.

Outfit #1

plaid midi skirt

There is a term I use with clients all the time when styling them.  If a look is too frilly or feminine, let’s stay, I will suggest we “cut the sweetness.”  This means to add something exactly the opposite in look to the outfit to bring in balance.  So in the case of a look being too sweet, I might add an edgy piece of jewelry or a more modern piece.  This is exactly what I am doing here with this plaid midi skirt outfit, I am cutting the matronly look of this skirt by adding in edgier or trendier items.  I also call this dichotomy dressing where two unalike things that don’t typically belong together are styled in one outfit.

The components styled with this skirt are what make this outfit look more updated and fresh, not the skirt itself.  I added this cognac suede moto jacket, a cropped sweater from Leith, modern bag from ZAC Zac Posen, brown booties from Vionic and scarf from Chan Luu.  When choosing jewelry I selected less traditional pieces; this gold hook leather bracelet from Miansai and ear crawlers from Bauble Bar.

Outfit #2

plaid midi skirt

In this next look I am cutting the traditional nature of this plaid midi skirt but in a different way.  I selected an easy tie-front shirt from Madewell and a denim jacket.  I finished the outfit with flat loafers in tan from Boden, a grey suede bag from Frances Valentine and modern collar necklace from Robert Lee Morris.

Outfit #3

plaid midi skirt

Don’t shoot the messenger when I tell you that when trends return they are usually ageist.  If you were to put an outfit like the one above on a woman over 50, between the skirt and the bow blouse, she would look probably look matronly.  Yet, if you were to put this outfit on a 22 year old, her youth alone would probably make the outfit look much cooler and updated.  Perhaps it is the age of the wearer that cuts the conservative look of the outfit.

Despite this bow blouse from Rebecca Taylor, plaid midi skirt being sort of hip and cool on a younger person, I still added some more modern pieces to complete the look.  I styled the outfit with these trendy taupe heels from Vince Camuto, an acorn brown quilted shoulder bag from MICHAEL Michael Kors and threader earrings from Stella + Ruby.

Outfit #4

plaid midi skirt
Taking the plaid midi skirt in a different direction, a retro, slightly quirky, one.  It’s a way of bringing a playfulness to a more traditional and stodgy silhouette.  I added a short sleeve shrunken merino sweater in merlot from Vince, a pair of burgundy tights from J. Crew and block heel mary janes in taupe from Modcloth.  I finished the outfit with a forest green bag from Vince Camuto and mustard colored beaded necklace.

Outfit #5

plaid midi skirt

This last look takes the skirt in a another direction, a more rugged one.  In my mind I was thinking something that would appear in a Ralph Lauren ad.  I styled the plaid midi skirt with a chambray shirt from J. Crew and cable knit sweater from, no surprise, Ralph Lauren.  I finished the outfit with cowboy inspired boots in cognac from Rebecca Minkoff, a fringe bag from Ten79La and turquoise earrings from Ippolita.

Shop for plaid midi skirts

I can’t say I’m totally sold on plaid midi skirts, but seeing them styled does help make them more palatable.  If you are ready to take the plunge, check out these additional styles.