I usually carry only one bag. I don't really like the feeling of wearing/carrying multiple bags.
For work I have the Longchamp Le Pliage, and I'll put my lunch in there too lol, keys, wallet, and cell are in my pocket because I wear scrubs to you.
Going out to eat or for events, only one bag.
The only time I carry 2 bags is when I bring my dog out. He gets 1 small tote for his water and treats (+ I'll put in my sunglasses and water bottle) and I'll carry a crossbody bag for my things (wallet, keys, cellphone, lipbalm). I will admit, there are times when I find it a hassle but that's just me lol.