Photo: Bob Hiemstra

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.