The Leather Day Satchel
This is the essential workhorse handbag. A medium to large top handle bag that can hold almost everything. Choose one in a neutral color leather like black or medium to dark brown (stay away from white and light beige, which reveal scuffs and stains more clearly). And steer clear from those with lots of hardware or logos. Those details can date your bag.
This may seem intuitive, but make sure you pick the correct bag for your size. It’s easy to fall in love with a bag without thinking about how it will look on you, until you take it out for the first time. If you’re tall, a diminutive handbag can get lost. (Or it might look like you’re carrying your daughter’s purse.) If you’re on the petite side, choose a bag that doesn’t look like you could get in it.