For a simple yet chic, everyday style, embrace just a smidgen of ankle peek-a-boo and rock some booties with a pair of cuffed up boyfriend jeans. Casual cool stars like Jennifer Aniston and Rachel Bilson are fans of the pairing. The added lift of the heel will add some sophistication, but the baggy silhouette of the boyfriend jeans and laid back look of this season's short boots make it an ensemble that can be worn even on the weekend. We love how both Daily Disguise and Good Life for Less rocked the look with a sweater and infinity style scarf on top. Daily's chunky knit is a little more dress up that Good Light light pullover. If she threw on a blazer it'd be an instant evening dinner outfit. Denim with neutral footwear is a great pairing for a classic style, but don't be afraid of some booties with wow factor like animal print or velvet!