When your sundress collection starts to dwindle due to overuse, spilled cocktails, or the damn cat, it's time to stock up. The issue then becomes: How do I afford all the adorable sundresses I'll need this year? Penelope's in Wicker Park has your answer; it comes in the form of this adorable dress from Jack. Made of 100% cotton, the lightweight print is flirty, sexy, and necessary. A cute cutout ensures that it looks just as good going as it does coming, and the price tag practically forces you to buy it. Don't be surprised if you leave Penelope's with tons of other summer-ready goodies, too.
Penelope's, 1913 West Division Street (at Winchester Avenue); 773-395-2351.
Navy Blanche Dress by Jack, $55, available at Penelope's.