Jane McCormick, 62; retired
Here's a dress that's all about color and uncluttered structure (CH Carolina Herrera, $1,500)—which suits Jane, who hates "anything poufy, flowery, frilly" and likes purple with her silvery hair. The belt is patent (CH Carolina Herrera), add heels to match (Fendi). Diamonds (Asprey earrings; Avicci bracelet) supply sparkle.
Sandra Jamron, 33; pharmacy chain co-owner
Bronze and plum stripes (the rep-tie kind) bring an unexpected menswear feeling to this bubbly dress (Rickie Freeman for Teri Jon, $640), and a wrap-style bodice makes the waist look smaller. Sandra is crazy for the jeweled ankle straps (Juicy Couture): "My eyes light up when someone says, 'Shoes!'" H. Stern earrings. Kara Ross cuff.