Last year, I spotted someone sporting an ultra-chic, slouchy hobo bag during my commute home. Soon after, I was seeing other cute, slouchy bags all over the place. From sharply dressed New Yorkers to ...

Scroll through the handbag section of luxury online shops and you’ll see a pattern of style names emerge—duffle, bowling, clutch and one that always seems misplaced: hobo. As fashion call-outs go, the ...