The Best Local Shops and Sites for Cool Kids Clothes and Accessories

The weather is finally cooling off, which means if you haven’t already stocked up on fall clothes for your kiddos, you’re probably scrambling to now! Support these local stores and sites to kick off the school year with a very important lesson: Shopping small is always in fashion.

For the Littles

Earth Cadets (online)

Kids Clothes: Earth Cadets
Notorious RBG — Kids Hand-Printed T-Shirt, $25

Not only are the designs of these tees and sweatshirts spot-on, but owner Krissy Callahan designs and screen-prints everything by hand in her Chicago home.

Monica & Andy

Kids Clothes: Monica & Andy
Spinning Skirt, $34

From super-soft loungewear to twirl-worthy tutus, this store is a preschooler’s dream come true. 2038 N. Halsted St., Chicago

For the Middles

Maya Papaya & Tony Macarony

Kids Clothes: Maya Papaya & Tony Macarony
Taco Truck Lunchbag, $21

The selection of unique shoes, outerwear, and accessories at this Central Street favorite can’t be beat. 1901 Central St., Evanston

The Red Balloon

Kids Clothes: The Red Balloon
Personalized Stripe Sweater — Letter, $88

Filled to the brim with clothes and accessories, this is the place to go for quality stuff you don’t see everywhere else. 1940 N. Damen Ave., Chicago; 3651 N. Southport Ave., Chicago

So Silly (online)

Kids Clothes: So Silly
So Silly Color-in-Chicago Kids T-Shirt, $27

Specializing in soft, durable tees kids can color themselves, this local site is a must-hit for everything from clothes to birthday gifts.

For the Bigs

Lola and the Boys (online)

Kids Clothes: Lola & the Boys
Unicorn Satin Bomber, $65

This Chicago-born site has something for every style, from boho-chic to rocker-chick, and specializes in rad boys’ clothing, too — think bomber jackets and patched denim.

More Shops We Love…

Half Pint Shop (online)

With a hyper-curated selection from brands like Oeuf, Ferm Living, Lorena Canals, and Gautier Studio, this shop-turned-site (and a MIB Best of 2018 winner!) is one of the city’s best-kept secrets.

Greyboy (online)

Gender-neutral tees, pjs, and vintage apparel (old-school Levi’s shorties for kids!) make Greyboy a must for basics. Even better, everything is drawn and printed in Chicago.

Lad & Lassie

The current owners’ grandmother opened the doors to this perennial favorite in 1953 — and today it’s stocked with everything from Lilly Pulitzer water bottles to Patagonia fleeces. 1115 Central Ave., Wilmette

Little Threads

Bag quality duds from brands like Appaman, Tea Collection, Chaser, and Hatley at this Roscoe Village shop. 2033 W. Roscoe St., Chicago


The gorgeous shop is styled like a high-end boutique meant for moms, but caters to the tween and teen set. 2138 W. Roscoe St., Chicago

Frankie’s on the Park

With two stores in Chi-town and another sand-side in Santa Monica, this tween institution knows exactly what the cool kids are wearing. 3708 N. Southport Ave., Chicago; 2322 N. Clark St., Chicago

My Sister Kate

Loaded with sought-after brands from Quicksilver and Lucky to Ella Moss and Splendid, the popular spot has a treasure trove of toys and gifts to boot. 48 S. Washington St., Hinsdale


There’s plenty for kids of all ages at this cute Northbrook shop (another MIB Best of 2018 winner!), but the selection of trendy clothes for tweens can’t be beat. 2750 Dundee Road, Northbrook

Clear some space…

Kids grow and go through clothes so fast it’s hard to keep up (sniff, sniff)! They also tend to grow out of their clothing long before they wear through it, so once your littles have moved up to the next size, be sure to keep those clothes out of the landfill by passing them along to a younger sibling, friend, or family member, or donating them to one of these worthy organizations.

More from Make It Better: 

Tracy CliffordTracy Clifford is one of the nation’s leading fashion stylists. She has developed deep experience in the fashion industry through buying and selling for top designers and luxury boutiques, representing designers in showrooms, styling photoshoots, and styling individual clients. Tracy loves to help clients feel beautiful and confident in clothes that are complementary, stylish, and perfect for their lifestyle. When Tracy is not working, you can find her shopping, reading up on the latest trends, and spending time with her husband and family. She is also an active member of The Scenemakers Board of the Goodman Theatre. Learn more at





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