Plaid! Plaid! Plaid! At this point, I have lost count of how many plaid shirts I own! My style tends to be very classic and basic, therefore I wear my plaids very clean-cut. I do like a little grunge flannel here and there but for the most part I keep it simple! I pair a plaid shirt with jeans, shorts, and leggings. Plaid will never go out of style.