Pop quiz: How cute is this shoe? Answer: (a) supercute. Continuing the menswear trends this fall (spectators, workshoes, kilties, oxford and wingtip details), the penny loafer by Jeffrey Campbell has an adorable rounded toe with a short vamp. Sawtooth edges, patent finishes and snakeskin patterning add a more feminine feel. Or not: Enzo Angiolini's Mendoza is a sober penny loafer straight out of the men's department and perfect under a subtle windowpane plaid wool pant for the office.
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The Mary Jane pump is a great fall trend and the O, Please by Gentle Souls with its clean lines, rounded edges and leather-covered button is a great example.
We threw in some cashmere tights by B.ella, an aubergine day bag by Pietro Allesandro that folds into a large clutch for after-school events and topped it off with a slouchy, plaid engineer's cap by San Diego Hat Company. The tights and bag will dress up the shoe, the cap adding a cool riff on the overall color scheme while tapping into this season's plaid addiction.
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Frye's Campus boot has been a hot commodity ever since the Civil War, though we associate it more strongly with college life in the '60s and '70s. The buttery caramel color of this stacked heel boot is eye-catching without being blatant.
We've paired it with a Mod engineer's cap in a wide, woven herringbone that picks up the boot's color. The grey of the cap works back to the Sterling silver in Wendy Culpepper's Louie organic shape necklace and HUE's knee socks in cobblestone blue. A Carla Mancini shoulder bag and a cute bird keyfob by Livishy add fun period touches.