Penelope’s

Jena Frey and Joe Lauer, the husband and wife team behind Penelope’s, are a rare kind of couple. With their brown hair, thick-rimmed glasses, and easy hipster style, the two look perfect together, like bookends. They talk in tandem, easily completely each other’s sentences, and it is obvious that Jena and Joe truly enjoy each other’s company. After spending a few minutes watching them in action, you get the feeling that any endeavor this couple decided to undertake together would turn out absolutely delightful.

Hence Penelope’s, a clothing shop for men and women named after the couple’s five-year-old pug. From its electric blue walls, to the colorful wood and wire Eames clothing hooks in the dressing rooms, to the handmade dollhouse used to showcase the earrings made by jewelry designer and Penelope’s employee Juliann (her line is called Tiny Jules), the store is full of unexpected whimsy. The clothes are no exception. Joe and Jena’s goal upon opening Penelope’s in the fall of 2002 when they were one of just three retail stores on Division (imagine how they’ve seen this neighborhood change!) was to develop a store where women and men could find casual clothes by designers not readily found in Chicago.

They have succeeded. With lines like Spring and Clifton, A.P.C., Brooklyn Handknit, and Built by Wendy, you will see right away that these clothes have a playful quality and prices that won’t make your jaw drop. My favorites are the Spiewak Uniform Workwear coats and the paper products by the Canada-based Lovely Design.

Added bonus: you need not fret bringing your boutique-phobic beau to Penelope’s. There is a vintage Ms. Pac Man machine in the store that he can play for free while you shop to your heart’s content.

Penelope’s
1913 W Division
(773) 395-2351