You know those memes about the fall girl in her riding boots and cable-knit sweater clutching a pumpkin spiced latte? That's me. I love fall and I love fall fashion, including all the classics like brown, burgundy, and—of course—plaid. These cheeky checked pieces come back every fall and winter, and they're continually beloved for a reason. But that doesn't mean fashion people can't find new ways to style plaid that actually feel fresh and current—and believe me, they do.
This season, I'm taking inspiration from some very cool girls on how to look totally fab in a plaid jacket, plaid skirt, plaid dress, and (obviously) a plaid button-down. I'll walk you through it, if you'll let me.
The trick here is light-colored plaid: It's unexpected and adds dimension to the browns, dark blues, and grays in the rest of the outfit. Plus, the contrast trim is really beautiful and calls back to the bucket bag, so the whole look has consistency.
I'm so sorry to tell you that this exact skirt from Miu Miu is sold out everywhere, but I have found a similarly colorful style that also has the advantage of costing a fraction of the price. Also, the exact coat is only available in Norway, but Atorie has a very similar style for you.
Phoebe Dynevor and Emma Watson are both loving plaid dresses this year, so I think it's safe to say it's a deeply cool choice. I love the understated yet universally chic color combo here.
I wouldn't blame you if you associated plaid shirts exclusively with Pinterest style circa 2014, but I'm also somewhat delighted to show you that a simple but good plaid shirt with jeans remains a fantastic outfit in 2025 and 2026.
This outfit, come to think of it, really isn't all that fresh at all—it's deeply classic. It's also proof that you should never be afraid to lean into tried-and-true lines and color combos when it comes to your fall outfits.
