If you’re looking for an upscale shopping experience, look no further than Southport’s multi-level Krista K Boutique. It’s had a 14-year tenure in Lakeview’s now-flourishing shopping district and has been widely touted as one of Chicago’s best fashion boutiques. Features for Krista K include the New York Times, the Wall Street Journal, InStyle, Cosmopolitan, and many others. Expect designer brands with designer price tags such as rag & bone, Elizabeth and James, Alice + Olivia, and Calypso.
Krista K Boutique, 3458 N Southport Ave, Chicago, IL, USA, +1 773 248 1967
Wolfbait & B-Girls was built on girl power and a serious appreciation for local art. The women-owned and operated independent boutique got their name from Chicago Confidential, a 1950’s guidebook that ‘defines wolfbait as girls who moved to the city looking for success, and b-girls as what they sometimes turn into.’ They sell threads from their in-house designers but also include pieces by over 170 local artists, so you’re sure to find something unique that you love.
Wolfbait & B-Girls, 3131 W Logan Blvd, Chicago, IL, USA, +1 312 698 8685
Penelope’s was opened in 2002 by a husband and wife who offer everyday clothing for all ‘with an emphasis on quality construction, smart design, great colors, and fun prints.’ Expect to find a lot of good basic pieces for your wardrobe at prices that won’t break the bank. They have tops, bottoms, shoes, accessories, and outerwear for both men and women and always have an expansive sale section with plenty under $50. And don’t forget about their home goods section, which includes this rug.
Penelope’s, 1913 W Division St, Chicago, IL, USA, +1 773 395 2351