Best Bet: ASOS’s Mario Leather Brogues

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With their high-contrast black-and-white body and solid sole, ASOS's leather brogues are the most comfortable option for long days at work or for a creative alternative to heels for a night out. Paired with a baggy sweater and cuffed jeans or a minidress, they're bound to catch the eye of street-style photographers come fashion week.

Mario Leather Brogues, $45.37 at ASOS.