9 Popular Clothing Stores in Chicago, IL

Last updated in October 2024
An image of a clothing store.

Chicago's got style, and when it comes to clothing, the city really knows how to deliver! With an incredible array of boutiques and shops, from trendy women’s boutiques in Lincoln Park to charming independent men’s stores, there’s something for everyone here. Imagine strolling through a boutique like Alice & Wonder, where shoppers can snag chic outfits and unique home accessories—all under $100. How cool is that? Or picture yourself at Chicago Style, finding the perfect suit for that upcoming wedding or event with the help of their friendly staff. But it doesn't stop there! If you’re on the hunt for something more edgy, Kiwi's Boutique celebrates curves with contemporary pieces that are anything but basic. Or if vintage is more your vibe, The Pop-Up in Bucktown is a treasure trove of curated finds and hard-to-find sneakers. With so many fantastic options, let’s dive into some of the best local spots to amp up your wardrobe!

1

Alice & Wonder - Webster

956 W Webster Ave

Chicago, IL 60614

(773) 708-9015

Alice & Wonder is an enchanting women's boutique located in Lincoln Park, Chicago, known for its delightful combination of trendy clothing and chic home accessories. With a commitment to offering only the best items under $100, it’s a haven for shoppers on a budget. Visitors rave about the inviting atmosphere and the wonderful service from the friendly staff, making it a go-to spot for unique gifts and chic fashion pieces alike.

What People Love

  • Friendly and helpful staff that make shopping enjoyable.

  • A beautifully curated selection of unique and trendy clothing.

  • Affordable pricing with many items under $100.

  • Great quality products that exceed expectations.

  • A fun and inviting atmosphere that feels like home.

What People Don't Like

  • Some customers experienced issues with return policies and customer service.

You Have to Try

  • The Chicago-themed apparel that makes for perfect souvenirs.

  • Unique accessories and gifts that are hard to find elsewhere.

  • Quality clothing items that are stylish without being overpriced.

  • The Mad Hatter brand hats, popular for winter fashion.

  • Exclusive items and fun trends regularly updated in-store.

2

Bliss & Belle Boutique

1011 W Armitage Ave

Chicago, IL 60614

(773) 687-9979

Bliss & Belle Boutique is your go-to shop in Lincoln Park for all the latest fashions. From trendy clothing to adorable accessories, they've got it all! The store boasts a friendly atmosphere, with staff ready to help you find pieces that suit your style. Plus, with new arrivals regularly, there’s always something fresh and exciting to explore. Whether you’re looking for a unique outfit or a special gift, you’re bound to find something delightful here.

What People Love

  • Fashion-forward and cute clothing that appeals to a variety of styles.

  • Incredibly helpful and friendly staff who provide great styling suggestions and support.

  • A constantly refreshed inventory, ensuring there's always something new to check out.

  • Affordable pricing for high-quality and trendy pieces, suitable for various budgets.

  • A lovely atmosphere that makes shopping there an enjoyable experience.

What People Don't Like

  • Concerns about the quality of some items, with reports of products not holding up after limited use.

You Have to Try

  • Cropped turtleneck sweaters that are stylish and versatile for various occasions.

  • Midi silk skirts that offer a sophisticated look and received compliments at events.

  • A selection of unique dresses, perfect for special occasions like weddings.

  • Fitness gear, including sports bras that are affordable and practical for active lifestyles.

  • Cute accessories and gifts, ideal for shopping for friends or special occasions.

3

Chicago Style

3949 W Madison St

Chicago, IL 60624

(872) 777-5485

Chicago Style is a beloved independent men's clothing store located in the vibrant city of Chicago. Since 1997, they’ve been specializing in providing high-quality suits for weddings, proms, and all sorts of events, making it a go-to destination for anyone looking to dress sharply. They also boast a full line of casual wear, ensuring that there's something for every occasion. The friendly staff is dedicated to helping shoppers find the perfect fit, making your visit all the more enjoyable.

What People Love

  • Personalized customer service that makes you feel like family.

  • An impressive selection of suits for weddings, proms, and other special events.

  • Reasonable and affordable prices that won't break the bank.

  • Helpful staff, especially John, Muhammad, and Mike, who know their stuff.

  • A welcoming atmosphere that makes shopping enjoyable.

What People Don't Like

  • Some concerns about the business practices, including payment methods and transparency.

You Have to Try

  • The suits for special occasions like weddings and proms – there’s a great variety!

  • Casual clothes with options that suit different styles.

  • Shoes and hats that complement your outfits perfectly.

4

Ford General

1712 N Wells St

Chicago, IL 60614

(872) 724-9513

Ford General is a stylish haven for those seeking high-quality menswear and unique lifestyle products in Chicago. Established in 2021, this cozy shop features a carefully curated selection from top European, American, and Japanese brands. Whether you're looking to elevate your wardrobe or find that perfect gift, you'll discover a warm atmosphere with helpful staff and an impressive range of clothing and accessories.

What People Love

  • Great selection of high-quality menswear from renowned brands.

  • Friendly and helpful staff are always ready to assist.

  • Unique clothing and lifestyle items not found elsewhere.

  • A welcoming and cozy shopping atmosphere.

  • Excellent craftsmanship with many US-made products.

What People Don't Like

  • Nothing!

You Have to Try

  • The uniquely tailored suits that fit perfectly right off the rack.

  • Comfortable hoodies made in Italy that add a touch of luxury.

  • Stylish accessories like hats and home items that enhance your wardrobe.

  • Diverse women's clothing collections that change up your style.

5

Kiwi's Boutique Inc

1015 S Western Ave #1

Chicago, IL 60612

(312) 421-3322

Located in the Tri Taylor area, Kiwi's Boutique is a fabulous spot for fashion-forward women looking for contemporary styles that celebrate their curves. The boutique specializes in offering clothing with amazing stretch and a chic, edgy vibe, making it a go-to for those wanting to enhance their wardrobe with unique pieces. With a focus on quality and a commitment to customer service, Kiwi's is not just a shopping destination but a welcoming hub for the community.

What People Love

  • Stylish, contemporary clothing that fits true to size and complements curvy figures.

  • Exceptional customer service that makes shopping a pleasant experience.

  • A vibrant selection of unique pieces that are often well-priced and of great quality.

  • Size-inclusive options that cater to a diverse range of body types.

  • A welcoming atmosphere and personal attention from the boutique owners.

What People Don't Like

  • A few customers faced issues with the return process, which left them feeling a bit dissatisfied.

You Have to Try

  • The unique denim collection, especially jeans that offer great fit and style.

  • Accessories that perfectly complement outfits and add flair.

  • The red romper, which has been a hit among shoppers for its bold look.

  • Pieces that embody the soft girl aesthetic, perfect for casual outings or special occasions.

6

Loop Vintage

1613 W Montrose Ave

Chicago, IL 60613

Loop Vintage is your go-to spot for everything vintage in Chicago, offering a delightful mix of home goods and clothing from the 1950s to Y2K. The shop is filled with carefully curated treasures, from unique graphic tees to stylish vintage finds that you won't easily stumble upon elsewhere. Located in a bustling neighborhood, it’s a friendly space where you can chat with the passionate owners, Jess and Greg, who genuinely care about their customers. Whether you're a vintage enthusiast or just looking for a cool piece to spice up your wardrobe, Loop Vintage is definitely worth a visit!

What People Love

  • The owners are incredibly friendly and knowledgeable, creating a welcoming atmosphere.

  • A beautifully curated selection of vintage clothing and home goods that changes frequently.

  • Great prices for quality vintage items, making it accessible for all budget ranges.

  • The shop feels nostalgic, with plenty of clothing that reminds visitors of their childhood or past eras.

  • A fantastic vibe with good music playing, making it a fun place to browse.

What People Don't Like

  • Some customers feel that certain items are a bit overpriced. The hours can be inconsistent, leaving some disappointed when arriving to find it closed.

You Have to Try

  • The graphic tees that capture a range of styles, from band shirts to unique prints, are a must-see.

  • Check out the vintage home goods and beautiful glassware that make for perfect gifts or a personal collection.

  • The custom jewelry made on-site, which showcases their creative talent.

7

Mary Walter Boutique

33 W Superior St

Chicago, IL 60654

(312) 266-1094

Mary Walter Boutique is a standout in Chicago's shopping scene, offering a relaxed and personal shopping experience. Known for its unique clothing curated from around the world, this boutique is perfect for anyone seeking to express their individual style. Owners Cameron and Erin bring their expertise to help customers find outfits that not only look great but fit their lifestyles. Whether you're in need of a new work outfit or something special for an event, Mary Walter Boutique has got you covered!

What People Love

  • Personalized and attentive customer service by the owners Cameron and Erin.

  • A unique selection of stylish and quality clothing that stands out from chain stores.

  • A relaxing and comfortable shopping experience.

  • Recent upgrades to the store's aesthetic make for a modern shopping environment.

  • A perfect spot to find outfits for any occasion, from casual to work to special events.

What People Don't Like

  • The no return policy on purchases can be a concern for some shoppers.

You Have to Try

  • The beautifully curated collection of elevated sportswear for casual outings.

  • Unique accessories that complement any outfit.

  • Stylish workwear options that mix professionalism with personality.

  • Gorgeous dresses for special occasions that you won't find anywhere else.

8

Stylish Sin

2773 N Milwaukee Ave

Chicago, IL 60647

(773) 645-1488

Stylish Sin is a fantastic destination for anyone in search of unique fashion finds in Chicago. Located near the Logan Square Blue Line stop, this two-story store features an eclectic mix of new styles upstairs and a treasure trove of thrifted pieces in the basement. Whether you’re on the hunt for bold statement pieces or looking to dig for vintage gems, you'll find styles that resonate with a variety of tastes, all while enjoying the welcoming vibe and great music in the background.

What People Love

  • Incredible selection of unique clothing and accessories that cater to alternative styles, from punk to gothic vibes.

  • Great customer service that makes you feel welcome and valued during your shopping experience.

  • Affordable prices and regular sales, making it easy to snag stylish finds without breaking the bank.

  • The fun and vibrant atmosphere, with events and even a dance floor to enjoy while you shop.

  • A fantastic combination of new and thrifted pieces, providing endless outfit possibilities.

What People Don't Like

  • Some shoppers feel the alternative clothing selection could be more extensive, suggesting that it leans heavily on standard thrift items.

You Have to Try

  • Explore the top floor for incredible rave and punk styles that scream individuality.

  • Don’t miss the basement, where thrifting transforms into a treasure hunt with loads of hidden gems waiting to be found!

  • Check out the stylish, affordable accessories that can add the perfect finishing touch to any outfit.

9

The Pop-Up (thepopup.com)

1753 N Damen Ave Lower Level

Chicago, IL 60647

(708) 581-6969

The Pop-Up is a standout secondhand shop located in Bucktown, Chicago, where you'll find a fantastic array of curated vintage and select clothing, accessories, and hard-to-find sneakers. The vibe here is warm and welcoming, thanks to the owner and staff who are deeply knowledgeable about fashion. Whether you're a sneaker enthusiast or just love unique clothing, this shop is a treasure trove waiting to be explored.

What People Love

  • Extensive selection of rare and vintage clothing and sneakers.

  • Friendly and passionate staff who provide great customer service.

  • Well-curated items that reflect current fashion trends and local culture.

  • A fun, chill vibe that makes shopping enjoyable.

  • Knowledgeable owner who takes time with customers and builds rapport.

What People Don't Like

  • Some individuals felt a lack of assistance during their visit.

You Have to Try

  • The unique collection of vintage sneakers that you won't find anywhere else.

  • Rare concert tees and streetwear brands like Supreme that are must-haves.

  • Kitchy apparel and jerseys that give you a blast from the past.

  • The friendly and personalized service from Kevin and the team that enhances the shopping experience.

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