Nothing signals the start of fall quite like a plaid shirt. The pattern has roots in Scottish tartans and later in workwear, where brushed cotton flannel kept people warm outdoors, and it still carries that rugged, comfortable feeling today. What has changed is the range of shapes. Oversized boyfriend fits work as light jackets, cropped versions pair well with high waisted denim and skirts, and heavier shacket styles with sherpa or fleece linings replace a coat on mild days. Color makes a big difference too. Red and black checks feel classic, rust and brown feel warm and earthy, while green, navy and purple plaids are a little more unexpected. Look for flannel that feels brushed and soft rather than thin, and check that the pattern lines up at the seams, which is a good sign of careful construction. A good one will last for many seasons.

Wear a plaid shirt open over a white tank or tee with straight jeans for the simplest outfit. Tie it at the waist to show a skirt or high rise trousers. Heavier overshirts can go over a knit sweater as an outer layer, especially with a wool scarf. Finish with ankle boots, loafers or chunky sneakers, and keep jewelry minimal so the pattern stands out. A cap or knit beanie leans into the outdoorsy mood.

Our honest take is that one good flannel shirt will get more wear than almost anything else you buy this fall. We would start with a relaxed fit in a classic red or brown plaid that layers easily over tees and under coats. Shacket styles with a lining are worth it if you live somewhere with mild autumns. Cropped versions are cute but less versatile. Wash flannel in cold water and air dry when you can, since high heat can shrink the cotton and dull the colors over time. Fold flannel rather than hanging it to keep its shape. If you want to keep browsing, I also put together Designer Shirts for Women and Fall Wedding Guest Outfits, From Velvet to Plaid.