Kilts gone wild might be the motto for this season's plaid-layering craze. Get a piece of the menswear action with a single dashing buy, like a tartan peacoat (Tommy Hilfiger, $340), or try multiples: Combine a large, vivid plaid with neutral, smaller-scale motifs, such as these glen plaid trousers (Loft, $80) and tweedy, checked fedora (Christys' Crown Series by Tony Merenda). Trista Sutter (here with daughter Blakesley) loves this outfit's warm, unfussy feel—a snappier alternative to her everyday mom clothes (once the ultimate single girl on ABC's competitive dating shows The Bachelor and The Bachelorette, she now has two children with her husband, Ryan). Her life is less about trends lately: "Paying out the wazoo at high-end boutiques is just not me anymore!" But she'll definitely give plaids a second glance when she's shopping the sale racks.
Shirt, Ralph Lauren Blue Label, $245. Shoes, Philosophy di Alberta Ferretti. Shawl, Liz Claiborne New York.