5 Reasons to Love Alice & Wonder: Playful Fashion with a Local Twist

There’s something about stepping into Alice & Wonder that instantly feels like Chicago wrapped in pastels, prints, and play. Founded by Ali Schaffer in 2015, the boutique started with a simple idea: fashion should be fun, warm, and a little bit whimsical. Today, Alice & Wonder has become a go-to for locals and travelers alike who want to wear their Chicago pride with style.

Here are five reasons we keep coming back:

1. City Spirit in Every Detail

From the iconic CHI baseball caps to cozy crewnecks with city slogans, Alice & Wonder manages to capture Chicago’s heart without feeling touristy. It’s merch you’ll actually want to wear — the kind that feels cool and local, not cheesy.

2. Pastels, Prints & Play

The shop is filled with soft colors, fun patterns, and unexpected finds that make you smile. It’s the kind of place where you might come in for a hat and leave with a sparkly card, a candle, and a new sweatshirt you didn’t know you needed.

3. A Boutique That Feels Personal

Ali’s background in PR shaped her vision for the store: she wanted to create a space where people could find “the little things that make life pretty fun.” The result is a boutique that feels like a friend’s closet — curated, thoughtful, and full of personality.

4. Gifting Made Easy

Looking for the perfect Chicago-inspired souvenir or a thoughtful gift? Alice & Wonder has plenty of small treasures — mugs, hats, cards, and locally themed pieces that feel special without breaking the bank.

5. Community, Not Just Clothing

Alice & Wonder isn’t just about what’s on the racks. The brand has built a loyal following in the city, connecting locals through collaborations, seasonal launches, and a shared love of style with heart. It’s more than shopping — it’s about feeling at home in a brand that celebrates community.

Why We Love It

At Locals World, we believe fashion is storytelling — and Alice & Wonder tells Chicago’s story in a way that’s lighthearted, stylish, and full of local pride. Whether you’re customizing a hat at their Southport location or grabbing a last-minute gift downtown, Alice & Wonder proves that playful fashion can still carry a sense of place.

Locations: Downtown & Southport, Chicago
Website: aliceandwonder.com

✨ This feature is part of our Locals World Chicago series.
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