Best Bet: Loeffler Randall Natalie Flats

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A great pair of flats that can be worn with both workplace-appropriate attire and casual weekend pieces is a worthy investment. Loeffler Randall's Natalie flats fit the bill — a sleek cap toe keeps the look on-trend but still polished, while polka-dotted haircalf adds texture and whimsy. The price tag may be a bit high, but the cost-per-wear renders them a smart buy.

Loeffler Randall Natalie Flats, $295 at Loeffler Randall.