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)
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
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
The selection of unique shoes, outerwear, and accessories at this Central Street favorite can’t be beat. 1901 Central St., Evanston
The Red Balloon
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)
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)
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
Crush
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
Peek-a-Boutique
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.
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Tracy 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 tracycliffordstyle.com.
