A stained tee shirt and Pull-Ups might work for Junior bouncing off the walls at home, but when you want to deck out the progeny in clothes as special as s/he is, you must get to one of Chicago’s distinctive indie stores for toddlers. You’ll find stylish, finely constructed items that are fun to browse and buy for moppets. Some with play areas and activities to keep tots engaged.

The Red Balloon
1940 N. Damen Ave.
Chicago, IL 60647
(773) 489-9800

Jennifer Pope’s The Red Balloon offers a friendly, knowledgeable sales staff; gift wrap as adorable as the teeny little outfits; an impressive collection of quality items; and amazing boys clothes – which are not easy to find elsewhere. In addition, you can utilize the shop’s “24 Hour Approval” program to “borrow” clothing risk free to try on at home. After shopping the distinctive selection of clothing, toys, and books, staff will gift wrap it for free. Ask about the “Birthday Club” that entitles customers to 10% off their entire purchase the whole month of their child’s birthday, and “Shop for Schools” which gives three percent back to a Chicago school of the customer’s choosing. Nice.

Little Threads
2033 West Roscoe St.
Chicago, IL 60618
(773) 327-9310

Little Threads, in Roscoe Village, stocks a wide variety of clothing for boys and girls, as well as accessories, toys, gifts and books. “Our clothing ranges from fashion pieces to every day wearables, and includes options from Made in the USA to imports from Spain and France,” explains owner Joanne Chamberlain Krakow. “We can special order from most of our brands and have it delivered to your door with no shipping or delivery fee.” Every Monday at 10:30 a.m. the “Storybook Mom” entertains infants and toddlers with her dramatic interpretation of children’s stories and the play area play area allows adults shop in relative peace while kids are entertained. The shop offers a semi-annual clearance sale so you can unearth deals on end-of-season goods, too.

Milani Boutique
50 E Oak St.
Chicago, IL 60611
(312) 587-0570

If Kim and Kanye lived in Chi, they would be all over Milani Boutique, Oak Street’s first haute couture shop for little fashion bugs. Established in 1993 by Lana and Joseph Batko, Milani offers high fashion European clothes that are hard-to-find elsewhere in Chicago. If little Liam and Emma just have to be outfitted in Versace, Fendi, Dolce and Gabbana and Roberto Cavalli, head to Oak Street with your debit card and hope Junior doesn’t have a growth spurt.

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Once Upon A Child
552 South Route 59
Naperville, IL 60540
(630) 416-9344

Take heed of the old folk song, Turnaround” and it’s lyrics, “Turnaround and you’re two, turnaround and you’re four, Turnaround and you’re a young girl going out of the door.” You buy a $100 outfit for your little darling and she’s busting out of it in mere months. Places like  Once Upon A Child make supreme sense offering gently used kids’ clothes, (as well as toys, furniture and equipment) with prices up to 70% off retail. The seven local shops stock like-new items that are great brands, styles, in excellent condition and in demand.

Baby Dolls Boutique
3727 N. Southport Ave.
Chicago, IL 60613 
(773) 525-2229

Baby Dolls is the definition of a boutique – oodles of unique one-of-a-kind pieces, and the majority of the kids’ clothing is hand-made here in the US and Chicago. Regulars Many refer to the boutique as a brick and mortor Etsy shop with its impressive clothes’collection as well as custom decorated shoes for infants and toddlers. Located in the Southport Corridor, Baby Dolls’ owner, Vanessa Rodriguez, designs her own label, p&b, and does many custom orders for locals as well as Cubs and Blackhawk families that fall in love with her line. Part of the proceeds from the shop’s exclusive p&b label helps fund partnerships with the nations top Neonatal Intensive Care Unit (NICU) hospitals in the country to help preemie patients.  

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Jacky Runice has been a columnist with the Daily Herald Chicago since grunge music and flannel was the new black. Her fingers and gray matter have been busy as travel editor of Reunions Magazine; penning a column that was syndicated around the nation via Tribune Media Services. Her work can be found at Examiner.com.