Valentino has unleashed the wild side of a proper lady, even the Upper East Side is seeing some edge to their bags. This classic shape (basically a Hermes Kelly) has gussets that flare out and studs that accentuate the clean lines. There are many options for wear, you can tuck in the gussets – unless of course you love that it looks like the Celine trapezoid bag. The top handle option is best since the drop is long enough to go over your shoulder. Comes in black or white but the black is a bit too obvious and rocker, the white shows more range in personality. At Luisa Via Roma for $2293.