Take a gander at these tricked-out fall booties, and you would never guess they are under 300 bucks. That’s the beauty of Jean-Michel Cazabat, who is as consistently style-conscious as he is price-savvy. This ankle boot has got it going on with an effortless mash-up of tweed (frayed ever so slightly for a great tough-girl attitude), liquid-y patent-leather toe, and chunky zipper embellishments.

Think of this pair as a fabulous leather-and-bouclé jacket for your feet: with uptown elements and a downtown spin, it’s a long-term staple that will go with everything from work to weekend to cocktail attire. A boot like this is great under pants, skinny or full, to casually expose the tweed, yet the low height works well with skirts and dresses (it won’t cut off your calves in an awkward spot), so this undoubtedly covers most of your needs for fall. At Saks Fifth Avenue for $295.

Pair with: Sparkle into the night with a cool orange sheath. Antonio Berardi’s sequined-front crepe mini is sure to dazzle, especially juxtaposed against a strong bootie. On Net-a-Porter for $3,410.