Weekender bags are the ones I would rather spend on than a big suitcase. The mix here goes from soft duffels by Calpak to structured totes from Saint Laurent, Marc Jacobs, The Row and Proenza Schouler. My rule is simple: if it fits under the seat and looks good on your shoulder, it is the right size. Pick the soft duffel for practical trips and the tote for the polished ones.

 

If you are weighing the two, Tote Or Weekender For A Two Night Trip helps decide.