If you're still stumped about what shoes to wear with denim, let Y2K outfits serve as a source ... Do you know who loves a long skirt and wedge boot combo? Today's top style icons.

We saved the best for last, that much maligned Y2K trend of wearing ... My problem is that all of my dresses are too long to make this work, and my skirts are too stiff or wide, so it’s just ...

For the record, I am all for the resurgence of Y2K fashion ... combine airy skirts with wide-leg styles, but you can def put together sleek, tailored ensembles when wearing dresses over jeans ...