I carried the same leather computer bag on my travels for decades. It is beat up now, but was perfectly serviceable until the day the shoulder strap hardware failed (no doubt due to my propensity for carrying multiple electronic devices and a couple pounds of power conversion hardware just in case my aircraft is forced to land in an unexpected and not completely civilized part of the world). The loss of that $5 part was the first of a series of small challenges that sent me looking at computer bags.
And there is a lot to look at. Hundreds of choices, each at its own price and quality level and all of them outside my area of expertise. I was overwhelmed for an hour or two.
What simplified my search was the decision that I wanted a very good looking bag with padding and just enough room for a laptop and an ebook reader. No more hauling power converters on board - they go in a suitcase now - or stuffing the compartments with books.
Simplification made looking around a lot easier. I quickly came to like the Mulholland Brothers deerskin laptop bag from my friends at San Francisco's On the Fly. It is padded, comfortable to carry, and too small to let me throw in twenty pounds of non-essentials as I am rushing out the door.
Of course, I liked the Mulholland luggage already. Their deerskin is great looking even if it does not yet have the patina it will acquire over time. It doesn't hurt that they had a family ranch not far from my house in Sonoma County. And, last but by no means least, On the Fly made the shopping experience easy for me.
One beat up Hartmann belting leather bag without shoulder strap is now looking for a worthy home.