I assume you already know about the renowned Magnificent Mile, so our list gives something new. In these neighborhoods, you will find the latest runway fashions, hipster looks and everything in between. – Patrice N. Perkins

Ukranian Village

Located just west of downtown and loved by the urbane and hip. Ukranian Village’s cool vintage shops and edgy fashion boutiques are a must-see. Check out the eco-friendly boutique, Green Heart. Then swing by Very Best Vintage, Penelope’s, Novem Studios, Pump, Post 27 and Kokorokoko.

Bucktown and Wicker Park

Grab your walking shoes and head to the bustling neighborhoods of Bucktown and Wicker Park. You will find luxe stores such as Nanette Lepore and Intermix as well as a nice selection of local boutiques. Check out Akira, The Silver Room, Francesca’s Collections, Gem, Michelle Tan and Robin Richman.

(credit: www.shoplakeview.net)

Southport Avenue in Lakeview


Just a few blocks from Wrigley Field, Southport is a must-do for the chic. The vibe is more laid back than that of Oak Street, but don’t let that fool you. Be prepared to “invest” in finds at Krista K, Tula and Red Head Boutique. Check out Chicago designers at Cerato Boutique. Other stops should include M2 Boutique, M4 Men and Mint Julep.

Oak Street


The main shopping district is one block north of the Magnificent Mile. Just a one — block stretch, but offers plenty of upscale options. Even if you don’t plan to spend, Oak Street is still interesting to see. Old townhomes and brownstones were converted into boutiques for our shopping pleasure- Hermes, Kate Spade, Tod’s, Jil Sander, Jimmy Choo and Barney’s, to name a few. Check out Sofia Vintage and The Daisy Shop for classic collections of vintage clothing.



Andersonville is home to fabulous boutiques offering a mix of nifty gift items and unique clothing. At the top of the list is Eva May- found only in Chicago and…Stockholm. The designer specializes in “wearable art” and offers really interesting pieces. For trendy men’s clothing, stop by His Stuff. Other places to check out are Presence, GreenSky and Paper Trail.

Patrice N. Perkins is the founder and editor of My Lifestyle ZEN, a Chicago-based lifestyle blog for professionals and entrepreneurs who value quality of life. Patrice provides work-life balance advice to readers as well as informs them on Chicago lifestyle.