Autumn’s Chicest Plaids

There’s something timeless about plaid—it manages to feel both classic and fresh with every season. From cozy flannel shirts that channel effortless weekend style, to equestrian-inspired capes that bring sophistication to cooler days, to skirts that add a polished, ladylike touch, plaid adapts beautifully to any occasion. In this roundup, I’m sharing my favorite plaid pieces of the moment—each one versatile, chic, and perfect for weaving a little pattern and heritage charm into your fall wardrobe. These photos were a part of a sponsored Lands' End IG story but I love them so much I thought they deserved a place on the blog!

• This simple plaid shirt is under $60 and an autumnal MVP. I love the unexpected color combination and feminine ruching on the back yoke. (Photo of the back below!) I like layering it over a cashmere turtleneck and Land's End has a really good version for under $200. It's super soft, a great slim but not tight cut, and the rib knit at the turtleneck is luxuriously thick and stands up nicely. (I'm wearing my normal size in both and love the fit.) Slim cashmere sweaters are a autumn/winter staple, and it's worth looking to round out your collection as some color are even on sale! (I'm wearing the rich saddle color above.)
• Shirt dresses are a favorite this time of year and this aqua and brown plaid version feels so fresh! I also like this shorter swing style with riding boots.
• This wrap wool skirt offers a more cosmopolitan take on the country classic. I love the idea of wearing it with a burgundy sweater and these knee high boots! For a more rustic vibe I love this fringe-y wrap skirt !
• I'm drooling over this dramatic plaid midi skirt. I'd style just like the model No notes.
• I'm all about equestrian-inspired pieces for fall and this autumnal cape is a beauty. (20% off with "Stacie20".) Whether you style it with jeans for apple picking or cream pants and riding boots like the model you can't go wrong. (I'd pair either look with this iconic bag.)
• A plaid shirt-jacket is just the thing to pop on this time of year and there are so many gorgeous options right now. Whether you want something like this houndstooth jacket that makes me think of apple cider, a royal blue number (20% off with "Stacie20"), or this navy plaid version that will go with everything.
• This pastel blue jacket is a feminine take on the staple, and great if you live in a warmer clime. Play up the autumnal vibe with tan suede accessories.
• Blanket wrap jackets have been around for a couple seasons and I especially love this plaid version. It looks fab with jeans and loafers or pair with a tapered trouser and heels for work or an evening out.
• This skirt drapes beautifully and can be paired with heels or boots.
• This funky green plaid blazer adds flair to a simple white button up and jeans.
• Pair these fab plaid pumps with any neutral dress for a festive look.
• A few feminine alternatives to a flannel shirt include this and this!

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