If you're still stumped about what shoes to wear with denim, let Y2K outfits serve as a source of inspiration. Pair flare jeans with sleek black boots and opt for a small kitten heel, much like ...

Katie Holmes's off duty style is the definition of effortless chic, and her latest outfit ... Y2K denim jeans to match in a medium blue wash. Holmes completed the look with a slouchy grey beanie ...