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I know people shy away from denim-on-denim, but it can work if you vary the tones, like this chambray shirt and jeans combo.

Classic, casual, chic look - black blazer, black and white striped graphic t shirt, distressed jeans, strappy sandals, and natural handbag. Black loafers would like good, wedge heel, or a short boot.

Ripped jeans, slouchy gray top, casual chic! Women's street style fashion outfit

These are growing on me. Shoe-boots/shoots/booties, or whatever they're called.