Krista K Boutique (Lakeview)
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
Milk Handmade (Andersonville)
For years, Milk Handmade has been a fixture on Andersonville’s main drag, and for good reason. The boutique sells unique women’s fashion pieces along with accessories, jewelry, and beauty products. It brings character and commerce to the North Side’s thriving Swedish neighborhood and sits among other local favorites such as bookshops, restaurants, and bars. Milk does partnerships with many strong women designers but also accepts online submissions for new additions to their store.
Milk Handmade, 5137 N Clark St, Chicago, IL, USA, +1 773 234 7053
Eskell (Wicker Park)
Two high school pals started Eskell in 2005 after a lifetime of being fashion-obsessed and talented with a sewing machine. Their initial focus for the boutique was ‘custom printed silk fabrics paired with simple cuts all tied together with their true love of great details.’ The women’s clothing they offer carries a distinct bohemian flair, complete with flowy fabrics and abstract prints. But their expansive selection also carries bags, jewelry, fragrance, and décor, among other things.
Eskell, 1509 N Milwaukee Ave, Chicago, IL, USA, +1 773 486 0830
Art Effect (Lincoln Park)
This mainstay in Lincoln Park has been serving up clothing, jewelry, home goods, and accessories for 20 years. It specializes in women’s clothing, which can be pricey, but offers quality brands like Velvet, Chrldr, and Fifteen Twenty. But their expansion beyond garments sets this boutique apart. This is the place to hit for any gifting opportunity in your life – from bridal showers to birthday parties. Not even the men and children in your life are excluded from Art Effect’s wide range.
Art Effect, 934 W Armitage, Chicago, IL, USA, +1 773 929 3600
Wolfbait & B-Girls (Logan Square)
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 (Ukrainian Village)
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
You don’t actually have to leave the Loop for all your quirky fashion needs. Just stop in at Florodora in the historic Monadnock Building for a display of vintage-inspired garments, gifts, and accessories. Also visit their sister store, Florodora Shoes, just down the hall. Both are currently throwing their semi-annual Scandal Sale with pieces up to 50 percent off. But if you miss out, they also host trunk shows every Friday featuring local area designers.
Florodora, 330 S Dearborn St, Chicago, IL, USA, +1 312 212 8860