$375, theoutnet.com

The one-two punch of the asymmetric hemline and graphic color-blocking makes this Derek Lam skirt a true standout. What's more, it's on sale (the original price was $1250). I'd team it with a casual t-shirt, just like uber stylish blogger Leandra Medine would...

1. American Vintage t-shirt, $57, matchesfashion.com
2. Dannijo lariat necklace, $326, shopbop.com
3. Nars Heatwave lipstick, $24, beauty.com
4. House of Holland striped clutch, $258, asos.com
5. Rosegold booties, $240, shopbop.com