Fun question! Especially because I used to write plaid off because I too didn't want to look like a lumberjill. Probably had something to do with the fact that when I was ages 10-12, I wore my older brother's hand-me-down plaid shirts day in and day out. They were masculine in both color and shape, but I loved the warmth of the flannel and the awesomeness of the plaid even then. I've since learned how to style plaid in classy ways -- it can be done!
A few thoughts:
Choose your plaid carefully. Classic plaids like the ones pictured below are safe bets. This isn't to say you can't pick something with pink or teal or yellow in it (although that color palette would lend itself better to a skater/boarder look)! But you're guaranteed chic when you go classic:
In terms of styling a plaid shirt, the key is mixing it with chic textures, colors, and accessories (with some feminine touches, to contrast the masculine plaid print). And I will now list my chic standbys: think black, gold, pearls, leather, tweed, chiffon, tulle, denim, boots, heels/flats, etc. Avoid wearing the shirt hanging open (unbuttoned all the way), or with chunky layers or anything that's too earthy or wooly if you're really trying to completely steer clear of lumberjack.
If you're working with a more modern plaid like the ones pictured below (i.e. a pattern with more "unorthodox" colors), keep the rest of your outfit more neutral so you maintain a streamlined look. Tuck it in, rather than wearing it un-tucked or open. Focus on the accessories/shoes: flats & jewelry can do a lot to chic it up.
Any other ideas for chic ways to wear a plaid shirt? Do tell!
The middle pic in the second set above (blonde hair/sunglasses/watch) is via Happily Grey.
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