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I've been using this as my everyday bag for errands with the kids and it works just as well for date night. The crossbody strap sits comfortably and it holds way more than I expected for something so compact.

Took this to a dinner last weekend and it sat nicely against my hip without swinging around. The flap closes securely but I can still get my phone out one-handed, which matters when you're chasing a toddler.

The strap adjusts far enough that it actually sits right on my hip instead of swinging around, which never happens with crossbodies for me. Took it on a full day of errands and date night after and it still looked put together. The classic shape goes with basically everything I own.