If you live in Chicago, you already know: we don’t do tiny bags.
We need room for survival gloves, snacks, backup flats, maybe even a blanket scarf for when the wind decides to humble us. Between long CTA rides, delayed buses, and random train moments that test your patience and your faith, a big bag isn’t a want it’s a lifeline.
Still, practicality doesn’t mean boring. The women here have mastered the art of staying warm, staying ready, and still looking like they stepped out of a street-style photo. Because in this city, accessories are the ultimate flex.
Lately, I’ve been deep in my “bag era” suede carryalls that feel luxurious, leather totes with oversized charms, and those statement bags that fit my Stanley, my planner, and my peace of mind. And apparently, I’m not alone. This season, fashion people in Chicago are choosing pieces that are big, bold, and beautifully functional — the kind of trending handbags 2025 that make you feel like you’ve got your life together, even when the Blue Line doesn’t.
These are the 10 best handbags for fall 2025 spotted all over the city from morning commutes to late-night hangs. They’re sturdy, stylish, and unapologetically practical.
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