I love plaid in theory but often worry about looking like a lumberjack while wearing it because I have a large chest. I like to layer it and also open up the buttons and tuck it into my pants to give a more polished look:
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Plaid: Old Navy (wearing an XL, it’s roomy and I could definitely wear a L).
Necklace: Kate Spade
Pants: Kut from the Kloth (similar here)