Plaid

The Test-Drive — Begin with just a peek of plaid. Layer a button-down beneath a cozy knit and statement necklace for a getup that doesn't scream Al Borland (unless that's what you were going for).

bebe Multicolored Geometric Statement Necklace, $39, available at bebe; L.L.Bean Kingfield Flannel Shirt, $39.95, available at L.L.Bean; Current/Elliott The Stiletto cropped low-rise skinny jeans, $93.60, available at The Outnet; MM6 Grey Sweatshirt, $195, available at Shop Nouvelles; Whistles Kir Royale Suede Boot, $247.50, available at Whistles.