Boutique Clothing Shops in Chicago To Refresh Your Fall Wardrobe

If you’re anything like me, you use every changing season as an excuse to spend money on new clothes, and there is no better time than the Fall season for a wardrobe refresh. As we get into some chillier temps and changing leaves, now is the perfect time to cozy up your closets by adding new items like sweaters, jackets, jeans, long-sleeve tops, you name it. So, check out these boutique clothing shops in Chicago with unique accents and styles to refresh your fall wardrobe like no other! If you’re a thrifter, we also have a list of the best thrift stores in Chicago for a weekend treasure hunt! 


1913 W Division St, Chicago, IL 60622

With fun prints, cozy textures, and so many on-trend pieces, you’ll be wondering why you haven’t stopped into Penelope’s sooner. At this independently owned boutique in Ukrainian Village, men, women, and children alike can find great clothes that’ll leave you wishing for cold weather and warm sweaters.


Laudi Vindi 

1007 W Armitage Ave, Chicago, IL 60614


Have you found the perfect leather bag for fall and winter yet? If not, a trip to Laudi Vindi is definitely in the cards. This independent leather goods store has the most beautiful bags, totes, cross bodies, and the ever-popular belt bag that can be used as the perfect accessory to any fall-inspired outfit you put together in the next few months.

Alice & Wonder

956 W Webster Ave, Chicago, IL 60614

​​3542 N Southport Ave, Chicago, IL 60657

If you’re a 20-something woman in Chicago, you definitely know about Alice and Wonder. In recent years, what started as a popular online boutique has become a staple stop for not only the trendiest clothes, but an entire line dedicated to Chicago apparel. In their words, “Chicago girls do it better”, and I’ll be purchasing one of everything. 

Knee Deep Vintage

1219 W 18th St, Chicago, IL 60608

In the heart of Pilsen lies the historic Thalia Hall, where you’ll find the incredible vintage store, Knee Deep Vintage. Here, take your time to perouse the racks, learn from the knowledgeable staff, and find an assortment of staple pieces and vintage classics that will become an everyday part of your Fall wardrobe. 

Art Effect

934 W Armitage Ave, Chicago, IL 60614

If you’re looking to stock your closet with pieces that range from casual to designer, Art Effect is the place for you. Not only do they have your wardrobe musts like tops and bottoms, but this modern-day general store also offers great things to spruce up your surroundings this fall like accessories, candles, games, and winter weather gear.

Alex’s Attic

2733 N Milwaukee Ave, Chicago, IL 60647

Alex’s Attic is truly a one-stop shop. Men’s clothing? Yes. Women’s clothing? You know it. A random pack of pencils or enamel cat pins? Yep! At Alex’s Attic, you’re going to find name-brand pieces without the name-brand prices, so feel free to shop till you drop. Your wallet and undying love of new clothes will thank you. 

Tribeca Boutique 

1035 W Madison St, Chicago, IL 60607

With new pieces arriving almost daily, I can guarantee you’ll be making multiple trips to Tribeca this Fall (and no, not the one in New York). Self-proclaimed as the “perfect mom and daughter store”, anyone who makes their way to the store this Fall is definitely going to find an outfit they’ll be loving for a long time. 

Monarch Thrift Shop

2875 N Milwaukee Ave, Chicago, IL 60618

Fall is the perfect time to thrift! When you’re looking for new jackets and sweaters, head to Monarch Thrift Shop. This 501(c)3 thrift shop uses its profits to support the fight against youth homelessness, rebuilding lives, and reducing recidivism. Finding great clothes and spending your money on a great cause? Win-win. 

Featured Image: Alice & Wonder