I similarly hate shopping. I find this forum interesting, but I'm not your typical participant in that I don't really follow clothes much. I largely post here to return the favor to a forum that helped me out many years ago, and to ask occasionally sourcingg questions.
I don't think the mail order route is going to be satisfying because it's going to have the hassle of returning clothes, etc. Below is what I do in order to minimize my shopping time. I wouldn't only advise this to someone that knows their personal style/tastes (in fact, I think it is almost the opposite of what such a person should do).
1) Get tailored clothes for as many things as possible. Things that fit properly will last longer.
2) Never buy things that are based upon current styles. Just buy what you like. That way things won't go out of style.
3) Buy high quality items so that they last longer.
4) Make a list of everything you think you'll need for the next year when you shop and make sure you fill that list. That list should have enough items to reasonably carry you through until the next time you want to shop. For example, my list will be something like: 18 button down shirts, 5 suits (two pairs of pants per suit), 6 pairs random wool pants, 4 pairs of corduroys, etc. If particular items wear out quickly, then buy several identical items.
5) Don't worry too much about prices. It just delays the process of shopping. There's an obvious cost of taking this approach, but you also need to factor in the value of your time. There can be some sticker shock when combined with buying in bulk per item #4 above.
6) Order things like underwear, undershirts, socks.
Except for picking up odds and ends, on average, I shop for clothes less than once a year. I make a list and then go to a handful of stores to fill that list. I pick the tailored clothes up when they are ready. I have the advantage of living in Manhattan where I can do this type of shopping trip in a few hours.
Aside from cost, the achilles heel of this method is that you can't let you body shape change much.
