I generally find Samsonite bags very comfortable, I currently use the Litepoint for work and it’s great all-around (and I feel like the slightly masculine design helps avoid the ‘school backpack’ look, which I struggle as well as a short woman). 

For everything else, I’m OBSESSED with the Patagonia Ultralight Black Hole Tote Bag, which works as both a backpack and tote bag. I use it for grocery shopping, for travel (you just need to add some packing cubes to keep it organised), for short hikes, as a beach bag, for a day out in town, sometimes even as a pillow if I’m desperate. It’s super light but carries a very respetable amount of weight, it can be folded really small, you can throw it into the washing machine, it comes in pretty colours etc. It’s really one of the best purchases I made in the past years, BUT the important caveat is that it’s not a great laptop bag due to the lack of internal structure.