Best Bet: The Gray Lady


The third season of Mad Men is in full swing, and we’re back to basking in the glow of the glam sixties clothes. This Joan Holloway–inspired dress packs subtly retro style without feeling kitschy. The built-in belt and side-skimming gold buttons create a shapely, curve-flattering silhouette, and the wool-blend fabric will hold up well in chilly fall weather with tights. And though the speckled gray dress is fit for the office, it can be dressed up or down with stilettos or boots.

Joanie dress, $64 at Fred Flare or online.