Autumn is a fab time of year to wear a plaid shirt. In Seattle plaid shirts are almost part of the culture, so good thing I’m a fan. This ensemble was inspired by my new fiery check boy shirt from J.Crew, which I’ve worn a lot with jeans and jackets over the last few weeks. It also matches my old tomato red skirt. 

Plaid shirts across all sorts of check designs are an iconic classic. These days, plaid fabrications are super soft and drapey, making them very comfortable. Most of them are casual and boxy, although dressier and more fitted versions are available too. I insist on semi-tucking or fully tucking my own plaid shirt so that I don’t feel schlumpy. A little structure can go a long way. 

Both of the outfits here were inspired by my wardrobe (you can see the exact items in the collection). I’ve worn the version with the jeans a couple of times and felt very happy in it. I guess the only thing left for me to do is get a faux fur coat and some cold weather pumps. 

Here are two ways to wear a plaid shirt. I like my own shirts bright or in high-contrasting neutrals, but feel free to sport ANY colour palette. 

Plaid Shirt, Jeans, and Bling

Combine a plaid shirt with trendy jeans like culottes or flared/straight crops and semi-tuck the shirt for structure if needed. Scrunch the sleeves for extra structure too. Add footwear that works with the silhouette of the bottoms. Add a bling necklace or a pile of pearls for a maximal effect. Add a topper like a blazer, moto, tweed or faux fur jacket. A shearling or wool vest will also work. 

Plaid Shirt, Skirt and Statement Topper 

Combine a plaid shirt with a pencil skirt, and top things off with a dramatic topper. I’ve chosen faux fur for drama. Finish off the look with footwear that works with the skirt, like pumps, booties, heeled loafers or tall boots. A bling necklace is optional. Add jewellery, eyewear and watch as desired.

Ensemble: Two Plaid Shirt Combinations