dr martens cherry booties range from fashion functional to fashion chic

“What other shoe transitions so well from day to night?” asked Elena Brennan, bootie aficionado and owner of South Philly’s Bus Stop boutique. “It’s one of the most versatile: cute with a dress, cute with jeans. Just cute.”

After making its functional fashion debut in the 1920s to protect women’s feet from dusty streets, the rugged and reliable shoe walked into high style in the 1980s with punk rock. Thanks to Dr. Martens and Timberlands, they remained in our fashion periphery through the 1990s, and in 2010, English designer Phoebe Philo introduced an open toe bootie for the Paris debut of her luxury womenswear collection, C

Since then, the bootie has been able to hang in mixed company that is both cozy and chic just as appropriate for a daytime stroll in dressy jogging pants as it is for a night on the dance floor complementing a little black dress. The boot comes in all varieties: caged and ankle height, mid calf and perforated, and sporty as if channeling high top sneakers.

But with so many kinds, it can be hard to choose which not just for cold weather shoe goes with your personality. Take our quiz to see which shoe bootie suits yours.
dr martens pinterest booties range from fashion functional to fashion chic