Best Bet: Lace Oxfords

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Photo: Courtesy of Annie Havlicek

For the past few seasons, New Yorkers have cultivated a fixation with wingtip oxfords. Annie Havlicek's lace-and-canvas variation blends masculine and feminine elements. The lace adds a bit of formality to the look — and would look great with a sweeping, maxi-length skirt — while the Osborn brand shoes were handcrafted in Guatemala City by local artisans. Take advantage of the shop's ongoing sale.

Canvas and Lace Oxfords, $50 (originally $125) at Annie Havlicek or online.