Serious yet sexy, these heels are feminized versions of oxfords and brogues—ladylike menswear for your feet. Try them with opaque or interestingly textured hose. (Clockwise from top left)
1. There's a desert-shoe feel to this smart platform heel; the red, more earth-toned than bright, is a good mixer. Bottega Veneta, $860.
2. Footwear suits up in a pepper-and-salt tweed punctuated with licorice-slick details. Marc Fisher, $89.
3. Cutouts aren't too bare for fall if you add ribbed tights; this lizard-look metallic pair can also gleam on into evening. Anne Klein New York, $255.
4. Green antiqued-leather oxfords combine refined lines with the rugged charm this bootmaker is known for. The Frye Company, $198.
5. Discreet peep-toes flirt with classic spectators in a handsome suede and patent leather hybrid. Coach, $318.