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And, to get started, Devil In A Blue Dress is a great place to begin

Thats why there are a few things you should keep in mind before styling your brown shoes with black pants

(No offense to Rory Gilmore and the students of Chilton Academy, but thats not really the vibe Im going for.) But a heel, whether its a one-inch platform or a four-inch block, helps add some shape to your leg and break up your boots silhouette

Common Projects Minimal Runner Sneakers These are on the pricier side of the spectrum but they are truly the epitome of simple and chic

The low vamp and padded insole made them ideal for sockless wear, especially in warmer weather