When I was among the employed I always maintained a small tool bag of my most used tools rather than carry the giant hard size case of crappy tools that work provided. Now that I am retired I still need a go bag of tools but clearly the mission has changed. I’m no longer the Aircraft Visual Landing Aid Tech Rep who worked on the light arrays that give your pilots a visual glide slope reference.
Now I’m the guy who goes from the house to my workshop or who runs to friends or families houses to help with more household chores. Bear in mind that this bag gets you from the truck to the house or shed. You can always go back to the truck for the 10 lb. crescent wrench.
In my opinion, canvas bags are the only way to roll for your tool bag. Tools are heavy. Your tool bag doesn’t need to add to that. Even though this isn’t advertised as a tool bag, my favorite bag for a small tool compliment is the Red Oxx Lil Roy EDC bag. It is almost perfect although I do wish it were an inch or two longer. Are you listening Red Oxx? Red Oxx bags are THE BEST. They cost a few bucks but I have never had one let me down. Carrying screwdrivers and other sharp things will expose a poorly made bag the first few times you toss it down or when it slides off the seat of your pickup truck.
My Lil Roy bag has nary a tear or defect after years of repurposing it as a tool bag. I love this bag so much that I got a couple more of them. The Olive color that I have the (stock) pic of hides dirt pretty well. After years of use my bag still looks pretty snappy. I’m not kidding when I say this bag has been through a lot and it still looks almost brand new.