My favorite work bags are the Jenn mentioned: Corcovado, Sonia and Trophy. But, I would also add the Beatrice.
The Beatrice and the Trophy bags have rolled straps. Of the two, the Trophy bag's strap drop is shorter than the Beatrice. I am 5'10" and a plus size and have to say that as much as I love the trophy bag (it is my favorite HH bag) it's straps are not an easy fit on the shoulder. The Beatrice fits more comfortably.
I would rank the bags in the following order:
1st Place: The Corcovado.
Flat straps with good strap drop. Versatility with its turnlock side-closures giving the user the option to tuck it in to a smaller size or expand for laptops and files.
2nd place: The Sonia.
Flat straps with good drop length. Three compartments lets you keep files and laptops separate from bagged lunch, LOL. Rank this one lower than Corcovado because, in my opinion, it is a bit more traditional. Less spectacular. But, its traditional styling makes it great for the board room. And, if you're like me and don't like the usual, kick it up a notch and get it in Anthracite.
3rd place: The Beatrice.
Like the Corc, it has versatility in its buckled, gusseted sides. It is big and handles more stuff than either of the two above. Ranked 3rd because of the rolled handles. Nice thing about how it fits on the shoulder is that it is quite slender towards the top (the portion that fits under the arm) and doesn't widen until towards the bottom. Rides like the old carpet bags - and just as comfy to carry.
4th place: The Trophy.
My favorite for looks, but the strap drop would be more comfortable as a shoulder drop if it was 1" longer. Not a problem with me because I wear my bags on the arm 90% of the time - but shoulder-bag lovers have said it can be tight when worn with a heavy winter coat. Again, on the plus side, it is a beautiful, stylish, rich-looking bag. It is the bag that all the
Gucci, LV and Hermes girls in the office ooh and aah over. They appreciate its quality and style... just can't let themselves go and get a bag without a branded look that announces itself to their public. Their loss is my gain.