We may earn revenue from the products available on this page and participate in affiliate programs.

Trends come and go, but you can count on these well-curated Chicago boutiques filled with popular brands and unique items to help upgrade your wardrobe—anytime.

handle with care Handle With Care located on Wells Street in Lincoln Park has been a Chicago staple for more than 30 years, featuring upscale women’s clothing and accessories. The shop is divided into two sides — one side is stocked with designer brands such as Diane von Furstenberg, Torn by Ronny Kobo, and Parker, and the other side features more affordable options, so there is truly something stylish and unique for everyone.

Handle with Care 1706 North Wells St, Chicago, IL 60614

adelaide If you’re a woman on the cutting edge of fashion, then head to Adelaide to shop the finest and most decadent of imported European fashions, including ever-evolving ready-to-wear designs and fashion-forward handbags, jewelry and shoes. Since its beginnings in the 1990’s, the boutique has been at the forefront of sophisticated and upscale fashion with a handpicked selection of innovative designs from artists such as Malo, Bruno Manetti, Azaara, Ischiko, Saverio Palatella, Cividini and Rundholz.

Adelaide 1704 N. Wells Street Chicago, Illinois 60614 

space519 This refined general store, located on Chicago’s Magnificent Mile, sells an assortment of unique and hard to find items across a broad range of categories from women’s and men’s apparel to home items to small furniture. The brands at space519 are also unique and lesser known, and often include statement jewelry pieces from brands like Dannijo and Eddie Borgo.

Space519 900 N Michigan Ave, Chicago, IL 60611

apartment number 9 If you’re a contemporary menswear enthusiast, then head to this Bucktown boutique that specializes in brands offering impeccable fit, high quality craftsmanship and subtle detailing. Apartment Number 9 aims to make men feel comfortable, cozy and stylish in their own skin and what they wear over it. They offer an exclusive array of pieces from designers including Band of Outsiders, Rag & Bone, Maison Martin Margiela, Shipley & Halmos, and Paul Smith.

Apartment Number 9 1804 N Damen Ave, Chicago, IL 60647

una mae’s Founded in the heart of Chicago’s Wicker Park area, Una Mae’s quickly gained its reputation for seeking out and selling a diverse and eclectic array of affordable men’s and women’s vintage clothing and accessories. This rustic-hip boutique is still known for their quality vintage pieces, but now houses an every-growing range of unique contemporary brands, accessories, household items, lifestyle products, and gifts.

Una Mae’s 1528 N Milwaukee Ave, Chicago, IL 60622

shop art effect Since owner Esther Fishman opened the modern day general store in 1984 to sell her artist-friend’s clothing and jewelry, the shop has truly evolved into a “one stop shop.” Art Effect involves a chic high-low mix of a constantly updated selection of women’s clothing, jewelry, and accessories alongside unique and stylish home décor and bath and body products.

Shop Art Effect 934 West Armitage Chicago, IL 60614

shop 857 Shop 857 is a locally owned boutique on Armitage Avenue in Lincoln Park filled with a well-curated collection of women’s clothing. Owner Kelli Kincaid has an eye for outfits and pieces that you’ll want to wear for any special occasion. The things you can expect to find at Shop 857 are a combination of classic, timeless items such as leggings, classic blazers and cozy sweaters for Chicago’s winters, as well as popular fresh patterns and trendy pieces.

Shop 857 857 W Armitage Ave, Chicago, IL 60614

soñador This elegant upscale men’s and women’s boutique on Armitage Avenue sells a small selection of unique European designer pieces, alongside your everyday denim and party frocks. Soñador carries the designer brands including Red Valentino, Missoni, 10 Crosby by Derek Lam, Milly, Moschino, and Victoria Beckham.

Soñador 1006 W Armitage Ave, Chicago, IL 60614

penelope’s Founded in 2002 by Joe Lauer and his wife, Jena Frey, Penelope’s is an easygoing Chicago neighborhood boutique in Ukrainian Village. The boutique’s aesthetic is clean and classic with an emphasis towards young designers. The store’s layout boasts a mid-century modern design and items are not organized by brand, but rather curated by color and theme.

Penelope’s 1913 W Division St, Chicago, IL 60622

kokorokoko vintage Located in Wicker Park, Kokorokoko is a colorful vintage shop that specializes in fresh 80’s and 90’s vintage clothing and accessories.  From authentic party outfits to eclectic sweatshirts and accessories, this shop is packed with one-of-a-kind finds.

Kokorokoko Vintage 1323 N Milwaukee Ave, Chicago, IL 60622

trillium This loftlike showroom in Wicker Park offers indie designer women’s clothing items and accessories, stocking styles from the brands Libertine Libertine and La Fee Verte. Owner Erica Cook is also very passionate about small designers in the Chicago community, and hosts in-store events to showcase their wares.

Trillium 1744 W Division St, Chicago, IL 60622

vividbraille Vividbraille represents international brands such as Opening Ceremony and Yuketen, as well as the store’s Creative Director Brock Willsey launched his own label in 2003 with designs that epitomize American-made craftsmanship and street style. This boutique also offers classes in crafty trades such as screen-printing, and also hosts events with other local artisans.

Vividbraille 2064 N Damen Ave Chicago, IL 60647

gallery aesthete Combining the elements of apparel, fine art, and design, this Oak Street art gallery and menswear shop displays cutting-edge fashion alongside thought-provoking art objects. Each item featured within the gallery has been carefully curated with regard to synthesis and precision. Designers include Rick Owens, Commes des Garcons and Ann Demeulemeester, as well as cult artisanal designers such as Guidi, Boris Bidjan Saberi and Julius.

Gallery Aesthete 46 E Oak St Fl 4, Chicago, IL 60611