The Chelsea boot is everywhere right now—and for good reason. It's trendy but extremely versatile and not so over the top that you'll feel uncomfortable sporting a pair. Wear them with your jeans casually tucked in a bit (Think: "It just happened, I didn't do this purposely") or pair with a suit for a less predictable office look. Pictured here: Steve Madden "Bedford" Chelsea Boot ($125, nordstrom.com).
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