If you have a sewing machine it takes less than 15 minutes to tailor a shirt down (just put it on inside-out, pin, and sew).
Made-to-measure mail-order dress shirts are an idea from the 1990s AFAIK. A while back I collected some promotional offers from in-flight magazines and online and ordered a big stockpile of white made-to-measure dress shirts. With the promotional pricing it came out to less than $20 a shirt.
As with any menswear business, the main problem is customer education. Men in the US dress like slobs, do not care that they dress like slobs, and do not want to spend money on clothes (85% of apparel revenue comes from womenswear).
The issue in my case is not the trunk. I'm a 'gentleman of size' (6'3 300 lbs) which means to find something that fits my neck, I have to buy a shirt large enough to accommodate another large person inside of it with me. I also, do not have a sewing machine, nor do I have a good place to work, or time to do it. I've had trouble finding a place locally that will do bespoke clothing.
I would rather not dress like a slob, but barring me finding a place to make me something that actually fits (for a good price).. everything I buy will fit somewhat awkwardly, and make me look as if I'm wearing several flower sacks sewn together or somewhat awkwardly in fit in other ways.
You can get a demo shirt from ModernTailor for $20 and then as many perfectly tailored shirts for under $100 as you want. As the earlier commenter said, these companies have been around for years.
Made-to-measure mail-order dress shirts are an idea from the 1990s AFAIK. A while back I collected some promotional offers from in-flight magazines and online and ordered a big stockpile of white made-to-measure dress shirts. With the promotional pricing it came out to less than $20 a shirt.
As with any menswear business, the main problem is customer education. Men in the US dress like slobs, do not care that they dress like slobs, and do not want to spend money on clothes (85% of apparel revenue comes from womenswear).