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Olivia Harris gives her textured leather hobo an industrial overhaul with zippers and a chain strap. Tout the tassel-clad bag with an oversized sweater and motorcycle booties for directional downtown chic.

MICHAEL Michael Kors eases the transition to evening with this leather crossbody. Ideally sized for day-to-night demands and packed with pockets, it's our desk-to-dinner must.

"THE LOOKOversized square shapeAllover honeycomb print with ""Naughty and Independent"" graphicOpen top with leather handlesInterior has open top accessory pockets and large zip pocketTHE MEASUREMENTLeather handles 9½"" drop15½""W X 17""H X 3""DTHE MATERIALCoated canvas/leather trimPrinted nylon liningORIGINImported"

Rock this retro diva-licious style from Nine West day and night. Decked out in shiny signature 9s and glam custom hardware, it's secure frame closure stashes cards, cash and ID, while the front snap pocket keeps your phone close in case you need to text your BFF on the dance floor.