Cheryl Shops

There's just something about plaid that says fall to me--I tend to feature it here every year. But while plaid itself is timeless, it can be updated to the trends of the season. So this year, while a full-on grunge revival might not be happening quite yet, a relaxed plaid shirt with a borrowed-from-your-boyfriend fit is definitely a must-have. (Bonus points if it's flannel.) Unlike the grunge era, when the entire silhouette was a bit baggy, however, the current plaid shirts look best paired with something snug-fitting, such as skinny jeans or even a bandage skirt. Think of it as the new glam grunge.

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You know what's not grunge? Paying $800 for a plaid shirt. But The Row takes a step beyond luxury with their 100% cashmere Burford shirt. Decadent, yes. But, like most of The Row's stuff, I bet it fits like a dream and is incredibly soft to the touch.


The detail in Kimberly Ovitz's Anthony blouse make it stand out: The front is asymmetrically pleated, and the fabric is a very fluid wool-rayon blend, making it both warm and light. It's a little fussy, yes, but it's perfect for those who don't want any old plaid shirt.


My favorite button-down shirts, hands down, are by Boy by Band of Outsiders; I tend to buy them online at Gilt Groupe sales or at The News Showroom's sample sales. They are not cheap, but they only get better with age, and they never gape at the bust. So I will definitely be looking out for this black and white plaid flannel shirt, which, from its simple color scheme to its easy fit, looks just about perfect.


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Very similar to the Boy shirt above is this boyfriend flannel shirt from Shopbop's reliable, reasonably priced in-house label, Bop Basics.


Also nearly perfect are Elizabeth and James plaid shirts, which nearly always sell out at full price. The Laurent plaid shirt, with its loose fit and faded look, is another winner.


If all of these relaxed silhouettes are making you wary, the Matata shirt from Paul & Joe features an additional button closure in the back so you can adjust the fit to your liking. (Hey, it's like two shirts in one!)


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This shirt from Zoa is perfect for those who like a little fancy in their plaid--it has gold-button epaulettes at the shoulders and a contrast bias-plaid pocket, and it's double-faced, meaning it's reversible, basically. Hey, it's the little things.


The plaid boyfriend shirt from 7 For All Mankind is not the most exciting shirt you've ever seen, but if you're like me, it will probably be the one you reach for the most.


Of course, there are many bargain options out there as well, and as you'd expect, Urban Outfitters is a great option. Their plaid flannel shirt comes in several different plaids; my favorite is the tartan below.