sessunblackdressLocated at the border of Wicker Park and the Ukranian Village, Penelope’s is a hip boutique that celebs love to peruse when they’re in town. It’s low profile but full of sweet finds for both sexes.

Around since 2002 —  which for this ‘hood and the average life span of a trendy boutique, means it’s practically a dynasty; the brands they love that you’re sure to find here include:

  • Our Legacy
  • Sessún
  • Gitman Vintage
  • Shades of Grey
  • Spiewak

They don’t stock up on enormous amounts of size runs which means little risk of seeing your look mirrored back to you on Michigan Avenue – collections change frequently so shop often!