THE IT: The Gap’s loafers

Suede fringed drivers ($59.50, gap.com)

Flats often need a little something extra to elevate them above being straight-up practical choices. With these loafers, sensibility is just a bonus. The suede is sweet, the fringe detailing is right on-trend, and the Elysian blue shade will have you walking pretty into fall.

—Manjit Gill