I generally put some of my foundation on my lips (I use Armani) and that has done more to make my lip products last longer through the day than anything else. I also have been using Charlotte Tilbury's Pillow Talk Pencil and I love the was the H lipsticks wear after that (I use both matte and shiny though I prefer the matte).
I'm very used to playing with my makeup. Lip products are several layers (foundation, pencil, H Lipstick, and I have been using a Pat McGrath gloss on top). That, plus I have a plastic piece under my mask so my lips aren't rubbing against the mask....if I'm not eating or drinking, this can last all afternoon into the evening, regardless of whether I'm wearing a mask.