The outlet mall that where I buy
Coach also has a Samsonite outlet and I bought a rolling backpack there to use on the train and while walking to and from the office. I use it when I am carrying my laptop and other heavier/larger items. It has places to hold an umbrella and a beverage. I usually drag it behind me but I can wear it as a backpack when it is snowy or slushy or when I have to climb stairs. I find it much more comfortable than carrying all that stuff in shoulder bags and I use it for my laptop when I travel on planes too.
I have a Vera Bradley mini cooler that is plastic coated, washable, light-weight and has a long, wide, adjustable strap. It is black and white and the pattern is pleasant. I use it to carry my lunch and it fits nicely inside my rolling backpack when I am using it.
I also carry a nice purse for personal items but I find that more and more that I use lighter-weight and patent leather purses because they are more practical for commuting. I also look for light-weight accessories to try and avoid heavy loads.
I try to never have more than 2 bags with me - my purse and the rolling backpack - or my purse and the mini-cooler. It is still a lot of stuff but I try to lighten the load whenever I can.