While I’m all about plaid flannels for cozy winter days, this classic check is getting a chic new update that I simply can’t resist! From flirty dresses to daring minis, structured plaid is one of our favorite trends for the season. Though this trend reminds me SO much of Cher from Clueless, she rocked it – and now you can too!

My tip for rocking the trend this season is to choose a piece that takes the workwear fabric into date night chic – like this daring V-neck mini dress! To spice up your look, try pairing it with bold white booties.

This plaid fit and flare dress is by far my favorite find this season. The cut of the dress is so flattering with the drop waist, and I love all of the details and stitching. Best of all, the shoulder pads add a bit of edge to the dress – and they’re quite slimming! While this dress may not be a steal, it’s classic, flattering, sophisticated, and I know I can wear it for years to come!

I’ve rounded up some of my favorite structured plaid pieces below for you to shop, and keep scrolling to see more of my look!

Shop Structured Plaid

Get the Look:

Alexander McQueen Dress // Christian Louboutin Heels // Gucci Handbag // Hermes Bangle // BudhaGirl Bracelets