When it comes to sexy and downtown-hip bags, nobody does it better than Gucci. Take this Gucci Romy Medium Tote for example. The black patent leather is edgy and cool, and the horsebit buckle (check out the metal grommets) and metal plates on the corners create a unique, chic bag that oozes with too-cool-for-school attitude. I also love the innovative handle. See, totes don’t have to be frumpy. Around $1,700 at Neiman Marcus