Roslyn, one of R29's favorite Chicago shops, is run by fashion mastermind Rosie Dulyapaibul, who also happens to have pretty darn amazing style. After years in NYC, Rosie wanted to move back home to Chicago, but needed to bring high-end fashion right along with her. Thank goodness her plan came to fruition, because now you and your besties get to shop hot brands like Elizabeth & James, Demi Lee, and Luxury Jones any time you want. Check out the Roslyn website for a complete list of designers, and get familiar, quick. If you haven't heard, Refinery29 is giving you the chance to win a $500 shopping spree at Roslyn. You'll even get to bring three friends to a private, after-hours shopping party and style session with Rosie herself. It's cool. You're welcome!