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It may lack the glitz and glam of LA and, for some, live in the shadow of New York, but the Second City has serious style — and is indisputably a first-rate shopping destination. Michigan Avenue's big-box shops and the international couture houses on Oak Street make up part of the equation, but for shopping experiences you can't get anywhere else, look to the city's amazing range of independently-owned stores.
From Andersonville to Hyde Park, there are more opportunities for only-in-Chicago retail therapy than you could comfortably cover in a weekend — featuring all manner of goods, too. This list of 19 homegrown gems includes everything from a game-changing boutique for women's fashion to an international streetwear powerhouse to a century-old apothecary.
So pack an extra bag because by the end of your trip, your suitcase will be stuffed to the brim with treasures like locally designed clothes, hard-to-find international labels, vintage jewelry, and then some.
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Ikram Goldman’s eponymous, glossy red boutique is a world-renowned destination for women’s couture. The 16,500-square-foot storefront bursts with interesting pieces by Givenchy, Moschino, and more, and there’s also an in-house café — a très chic lunch spot for ladies who shop.
High-end home goods fill this established Wells Street spot, where it’s all about that coveted mix of unique and sophisticated items: dinnerware and flatwear by Christofle, locally-designed Meghna jewelry, scarves by Faliero Sarti, and more.
Straddling the line between art gallery and menswear boutique, this sleek showroom, which reopened in a new location this past June, displays cutting-edge fashion alongside art objects, all with a common thread: a deep reverence for detail and material.
The buyers at this home store circle the globe to keep its roster of modern and vintage furniture, lighting, pillows, textiles, and tableware impeccably fresh. When sending flowers is in order, you can also score a pretty arrangement from the floral department. And the shop's annual fall flea market — complete with DJ-spun tunes and local brews — is not to be missed.
Initially a pop-up shop for high-end consignment, Luxury Garage Sale blossomed into a chic boutique stocking pre-owned and new designer pieces from a network of consignors and boutiques all over the world. We’re talking Chanel bags, Alexander McQueen dresses, Pierre Hardy pumps, and vintage jewelry.
Founded in 1857, this family-owned, old world–style beauty emporium carries more than 14,000 lotions, potions, and beauty products from international labels. In 2014, the shop expanded into its neighboring storefront to debut the men’s shaving and grooming mecca Q Brothers.
From the basement of a Hyde Park apartment building, this hallowed, circa 1961 neighborhood bookshop teems with nonfiction, cookbooks, kid’s titles, and more. The store’s events calendar is chock-full, too, and features kids’ story time, poetry readings, and author signings. A well-read staff is an added boon.
A lifestyle boutique juxtaposing pop art with high-end men’s streetwear, RSVP Gallery has a global following and even counts Kanye as a fan. The buyers bring in hard-to-find merchandise from Paris to Tokyo to Milan, plus staples from labels like Haider Ackermann and Acne Studios, as well as an in-house athleisure-leaning collection. (Aside from unisex items, the women's selection is limited to accessories.)
In addition to holding the unofficial title of Chicago’s most Instagrammable shop, this charming, minimalist space showcases a stellar variety of goodies, including jewelry, home décor, greeting cards, apothecary items, plants, and books — all created by small indie makers.
Logan Square landed its first high-end women’s boutique last year with the opening of Felt, which offers the handiwork of both established and emerging designers from London, Paris, Korea, and LA alongside rack space devoted to Chicago talents such as C/FAN and J. Markell. As a bonus, co-owner Catherine Dunton offers a trunk club service, sending personalized outfits that clients can choose to keep or ship back. (For more designer wares, check out VMR and nearby Tusk — but if you only have time for one, Felt should be the place.)
Amid some of the city’s best restaurants, you’ll find a tasteful grab bag at Rider — including vintage furniture, apothecary items, a well-edited selection of women’s clothing, and costume and fine jewelry — all inspired by the owners’ world travels. An in-store coffee bar offers a bespoke blend from Bow Truss, plus organic cotton candy and small-batch chocolate.
Named after owner and antiques fiend Julie Fernstrom’s favorite plaid, Brimfield holds an eye-catching array of home goods that skews English cottage-chic. There are antique and vintage curios, plus reclaimed furniture — and, of course, plenty of plaid. The basement level holds additional stuff, including barstools and vintage signage, and the shop also offers custom furniture and upholstering services.
With a fashionable husband/wife duo at the helm, Penelope’s allows guys and gals (and kids, too) to shop simultaneously, picking up fun, accessible duds from lines including A.P.C. and Mollusk. There’s also a great selection of giftable accessories.
Run by Chicago native Susie Lee, this Wicker Park shop strikes the perfect balance between California boho and city slicker edge. The bright shop stocks sometimes quirky, always chic designs from labels as different as UK-based Lazy Oaf and LA's For Love & Lemons.
Heads up, holiday shoppers: Local jewelry designer Susan Wheeler — whose ethically sourced gold and platinum creations are known for their cool textures — has temporarily set up shop in Logan Square. Through the end of the month, peruse the gift-worthy rings, earrings, and necklaces on Tuesdays, Fridays, Saturdays, and Sundays.
This minimalist storefront stocks vintage and contemporary men’s and women’s clothing, shoes, and jewelry, plus ceramics, prints, books, and records; thanks to owner Mary Eleanor Wallace’s collaborations with other artsy types, the goods are constantly evolving. Stop by on December 18 from 12pm–6pm to shop a group exhibition featuring 20 different small objects and their cardboard jigsaw puzzle counterparts.
Chicago-based Azeeza Khan showcases her eponymous line, Azeeza, at her flagship boutique. Khan counts the likes of Sarah Jessica Parker and Sophia Bush as fans, and her creations — eye-catching arrays of luxe silks and hand-woven, bejeweled embellishments — all but scream “holiday party.”
The super-compact shop manages to pack in clothing, jewelry, and handmade apothecary items, plus vintage clothing and accessories (ranging from 20 to 100 years old). Keep an eye out for frequent trunk shows and sales that double as cocktail parties.
What began as an online-only dealer of men’s clothing and accessories has blossomed into this lounge/shop/factory hybrid where everything is designed and produced onsite (yielding palatable price tags). Unfussy garments are aimed at the everyday dude; shoppers are known to stick around for a game of pool and a cold one on draft.
Ikram Goldman’s eponymous, glossy red boutique is a world-renowned destination for women’s couture. The 16,500-square-foot storefront bursts with interesting pieces by Givenchy, Moschino, and more, and there’s also an in-house café — a très chic lunch spot for ladies who shop.
High-end home goods fill this established Wells Street spot, where it’s all about that coveted mix of unique and sophisticated items: dinnerware and flatwear by Christofle, locally-designed Meghna jewelry, scarves by Faliero Sarti, and more.
Straddling the line between art gallery and menswear boutique, this sleek showroom, which reopened in a new location this past June, displays cutting-edge fashion alongside art objects, all with a common thread: a deep reverence for detail and material.
The buyers at this home store circle the globe to keep its roster of modern and vintage furniture, lighting, pillows, textiles, and tableware impeccably fresh. When sending flowers is in order, you can also score a pretty arrangement from the floral department. And the shop's annual fall flea market — complete with DJ-spun tunes and local brews — is not to be missed.
Initially a pop-up shop for high-end consignment, Luxury Garage Sale blossomed into a chic boutique stocking pre-owned and new designer pieces from a network of consignors and boutiques all over the world. We’re talking Chanel bags, Alexander McQueen dresses, Pierre Hardy pumps, and vintage jewelry.
Founded in 1857, this family-owned, old world–style beauty emporium carries more than 14,000 lotions, potions, and beauty products from international labels. In 2014, the shop expanded into its neighboring storefront to debut the men’s shaving and grooming mecca Q Brothers.
From the basement of a Hyde Park apartment building, this hallowed, circa 1961 neighborhood bookshop teems with nonfiction, cookbooks, kid’s titles, and more. The store’s events calendar is chock-full, too, and features kids’ story time, poetry readings, and author signings. A well-read staff is an added boon.
A lifestyle boutique juxtaposing pop art with high-end men’s streetwear, RSVP Gallery has a global following and even counts Kanye as a fan. The buyers bring in hard-to-find merchandise from Paris to Tokyo to Milan, plus staples from labels like Haider Ackermann and Acne Studios, as well as an in-house athleisure-leaning collection. (Aside from unisex items, the women's selection is limited to accessories.)
In addition to holding the unofficial title of Chicago’s most Instagrammable shop, this charming, minimalist space showcases a stellar variety of goodies, including jewelry, home décor, greeting cards, apothecary items, plants, and books — all created by small indie makers.
Logan Square landed its first high-end women’s boutique last year with the opening of Felt, which offers the handiwork of both established and emerging designers from London, Paris, Korea, and LA alongside rack space devoted to Chicago talents such as C/FAN and J. Markell. As a bonus, co-owner Catherine Dunton offers a trunk club service, sending personalized outfits that clients can choose to keep or ship back. (For more designer wares, check out VMR and nearby Tusk — but if you only have time for one, Felt should be the place.)
Amid some of the city’s best restaurants, you’ll find a tasteful grab bag at Rider — including vintage furniture, apothecary items, a well-edited selection of women’s clothing, and costume and fine jewelry — all inspired by the owners’ world travels. An in-store coffee bar offers a bespoke blend from Bow Truss, plus organic cotton candy and small-batch chocolate.
Named after owner and antiques fiend Julie Fernstrom’s favorite plaid, Brimfield holds an eye-catching array of home goods that skews English cottage-chic. There are antique and vintage curios, plus reclaimed furniture — and, of course, plenty of plaid. The basement level holds additional stuff, including barstools and vintage signage, and the shop also offers custom furniture and upholstering services.
With a fashionable husband/wife duo at the helm, Penelope’s allows guys and gals (and kids, too) to shop simultaneously, picking up fun, accessible duds from lines including A.P.C. and Mollusk. There’s also a great selection of giftable accessories.
Run by Chicago native Susie Lee, this Wicker Park shop strikes the perfect balance between California boho and city slicker edge. The bright shop stocks sometimes quirky, always chic designs from labels as different as UK-based Lazy Oaf and LA's For Love & Lemons.
Heads up, holiday shoppers: Local jewelry designer Susan Wheeler — whose ethically sourced gold and platinum creations are known for their cool textures — has temporarily set up shop in Logan Square. Through the end of the month, peruse the gift-worthy rings, earrings, and necklaces on Tuesdays, Fridays, Saturdays, and Sundays.
This minimalist storefront stocks vintage and contemporary men’s and women’s clothing, shoes, and jewelry, plus ceramics, prints, books, and records; thanks to owner Mary Eleanor Wallace’s collaborations with other artsy types, the goods are constantly evolving. Stop by on December 18 from 12pm–6pm to shop a group exhibition featuring 20 different small objects and their cardboard jigsaw puzzle counterparts.
Chicago-based Azeeza Khan showcases her eponymous line, Azeeza, at her flagship boutique. Khan counts the likes of Sarah Jessica Parker and Sophia Bush as fans, and her creations — eye-catching arrays of luxe silks and hand-woven, bejeweled embellishments — all but scream “holiday party.”
The super-compact shop manages to pack in clothing, jewelry, and handmade apothecary items, plus vintage clothing and accessories (ranging from 20 to 100 years old). Keep an eye out for frequent trunk shows and sales that double as cocktail parties.
What began as an online-only dealer of men’s clothing and accessories has blossomed into this lounge/shop/factory hybrid where everything is designed and produced onsite (yielding palatable price tags). Unfussy garments are aimed at the everyday dude; shoppers are known to stick around for a game of pool and a cold one on draft.
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