5 of 8
A tricky style, but it can look incredibly fashion-forward when worn correctly. Invest in a tailor to hem it to just the right length.

What type of shoes it works with: Menswear flat, pointy flat, kitten heel, t-strap heel, and bootie.

From left to right: Menswear flat, AGL, $370, agl.it for stores. Pointy flat, Via Spiga, $185, Lord & Taylor, 800-223-7440. Kitten heel, Kate Spade New York, $328, katespade.com. T-strap heel, Tory Burch, $425, toryburch.com. Bootie, BCBGeneration, $118, bcbg.com for stores. Skirt, Robert Rodriguez Collection, $465, neimanmarcus.com