Originally Posted by
Polytonic
I don't know offhand who might be willing to work on a bag, but there are a couple tailors in the area that are pretty good if you need regular tailoring work (e.g. alterations). In particular, one in Dupont, and one in Georgetown, though both are $$$$ levels of pricey.
Others here have suggested going to a cobbler. I personally would go to someone who, in addition to shoe repair, does general leather repair, and even better makes custom motorcycle saddle bags. This won't help you because I live near Chicago, but I recently discovered a shop near my home that does all of the above.
The bag I use is a Rick Steves convertible rucksack I've owned for 15 years. The only real problem I have had with it was on a Delta CRJ 700. I carried my bag to my seat in the rear of the aircraft, where the FA stationed nearby said it wasn't going to fit. I was ready to follow her instructions once everyone boarded, but she took pity on me by securing my bag to an unoccupied seat. I had never been on anything smaller than a 737 before, and I must have missed some information while preparing for the trip.