The SO Carriage Ballet Flat offers a more refined look than the other daring shoes on our list. With its clean plaid pattern, this shoe is preppy with just a hint of sass. Wear it with a crisp cream power suit for an office meeting, or with wide leg denim for a more casual affair.

On sale for $11.99 (regular $29.99) at www.kohls.com and Kohl's stores nationwide