This is actually quite easy.
LV Babylone. Functional and gorgeous at the same time. The brown go-with-anything bag.
Le Sport Sac Lulu minibag with the fruit design. Gracious, the number of compliments I get on that sucker is astounding. Totally casual.
Sigrid Olsen drawstring tote in black. Great leather, fabulous price, can be dressed up or down, and it will hold a ton.