Steve Madden Handbag, Bdayle Convertible Hobo

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.

Soft, comfy leggings with a cute cable pattern by Lauren by Ralph Lauren.

With signature quatrefois G monogram print punctuated with polished silver-tone hardware, this GUESS design is slender enough to slip into a bag and eye-catching enough to carry as a clutch. Plenty of card slots, pockets, and zipped compartment offer exceptional organization within.

A lady-like silhouette gets an edgy upgrade with this downtown design from The Sak. With a plethora of pockets, generous interior and utilitarian hardware; it's an obvious example of urban-chic style.