How would I find a place in DC that could make some custom-made dress shirts for me?
Welcome to my world. I wear a 16/36 dress shirt. You can try two things: a) move down a size. This generally helps for the “party” shirts. I can get a decent selection of medium talls from banana republic (online) A tailor can also help you with your issues. Tailors can pretty much do anything with a shirt, as long as the shoulders fit right. So, they can take in the sides, and make it as fitted as you want. They can also shorten those really long dress shirts for you. Don’t go the custom route unless you want to pay $$$. I’m sure there are a lot of tailors in the DC area, but the shirts will probably run you $150 a shirt. You can try doing custom made shirts online (mytailor.com), and do it online. You’ll have to provide your own measurements, and it might take some time to get it right, but after a few iterations, it’ll be spot on (and they have a huge fabric selection).
I haven’t gotten anything from them yet, but there is a shop in Alexandria that advertises custom-made shirts at pretty reasonable prices. It’s on Duke Street in a little plaza, right next to Shooter McGee’s tavern (which is 5239 Duke St Alexandria, VA 22304). I haven’t been by there in a few months but if they’re like any of the other menswear stores they might be doing specials right now. You would either need a car to get there, or take Metro+bus, since it’s a fairly good walk from the nearest station. (I think the nearest one would be Van Dorn Street station.
