Since May 2004 I have lost 100 lbs. (more than half due to sickness.) I have almost 30 dress shirts (I like to take 20 to the dry cleaners and still have a week’s worth of shirts left.) Can they be altered? Would it be more economical to simply replace them?
I’d say buy new ones. The shirts will have to be completely taken apart in order to resize them (collar has to come off and be reshaped completely, body has to be taken apart and cut down, sleeves may have to be altered as well). That’s alot of work.
Treat yourself to new shirts.
Maybe shrink the heck out of them.
What Plnnr said. That’s a lot of labor, and unless they’re some kind of Savile Row custom-made shirts, I’d bet that you’d pay more just for the tailor’s time than you would for completely new shirts.
Yeah, as long as that 100 pounds included at least 4" off the length of your arms, you’d be good with that.
Seriously, do you have any friends who are heavier than your size now, who have recently GAINED weight and might be willing to trade you some shirts? (Doesn’t have to be an even trade for the shirts you now have, it could be for home cookin’ or what have you.)
Also, if you need a home for your now-outsize dress shirts, you could consider donating them somewhere that they will go to a low-income person, and greatly help them in getting a job where they have to dress nicely. As you probably know well, dress shirts are NOT cheap, and the larger sized ones are even less so; one of the biggest barriers to getting a good job, when you are really poor, is lack of a suitable wardrobe.
I could probably remake a dress shirt fairly easily, but remaking it into a smaller-sized dress shirt (and not, say, a lace-up bodice or something like that) would be way too much trouble. New shirts, I say-- or at least new to you!
Corr
I was afraid of that. Normally money would not be an issue, but my current medical bills have me in debt that is usually beyond my comfort zone. Tack on the fact that I need to replace both my furnace and my air conditioner and I’m looking at some major debt.
Ah well, I guess a little more won’t really change the quality of my life any. 
Thanks for the replies.
How do the shirts look on you? Also, how much has your neck size changed?
If you are tallish and long-limbed, you might be able to get away with continuing to wear the shirts. Even if you’ve lost two inches off your neck (assuming a snug neck fit 100 lbs ago), the shirt might still look acceptable … and be much more comfortable to boot.
How do the bottom ends of the shirts fit when you tuck them into pants? Do they wrap around your body like a burrito? Or do they gently gather here and there?
Based on my experiences with large amounts of weight loss I’d advise you to just put them away for now. If you don’t need them again in 5 years then give them away, but don’t try to re-tailor them it’s a waste of time.
If the shirts are in good shape (sounds like they are), you could take them to a used clothing store or a consignment shop and get some of your original investment back. And you might even find some shirts there that will fit you, for cheap.
Hmmmm. Good advice for most people, but in this case I don’t think it will be a problem. They have effectively removed my stomach. I am told that I will actually have to work to keep my weight up. Even if I am able to gain a few lbs back (and the Doc thinks I will lose 30 more, not gain) I doubt I will be able to gain a 100 lbs back.
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How do the shirts look on you? Also, how much has your neck size changed?
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I don’t know yet. Although I am out of the hospital, I am currently not able to return to my house until I am able to live alone. I am rather doubtful though that they will look OK on me. They weren’t tight to begin with and the necks were a little too big too.
Oh well, I can start out small and ask lots of people for shirts for XMas.
Wait a few weeks and you won’t immediately need to replace your air conditioner.
Seriously, though, congrats on your weight loss (I hope it wasn’t through illness), and I’d vote for donating the shirts (there are several homeless shelters in your area that have job training).