Calvin Klein Handbag, Brasil Pebble Leather Crossbody

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.

A little extra protection never hurts. This super floppy hat from Nine West is your new best friend for pool-side relaxation. With a packable design, just stash it in your bag for easy on-the-go travels.

Marc Jacobs toughens up this ladylike silhouette with luxe leather and chainlink hardware in this mini version of the iconic Stam bag.

This kate spade new york shoulder bag blends practical allure with on-trend panache, crafted in leather and finished with classic, turnlock hardware.