A service I'd pay for: I send you a photo of myself, my measurements and money. You make me look good.
I think this exists. I can't think of any names but I know I've heard of basically this concept.
That person will guide you throughout the day while you go out and buy the stuff society at large would like to see you wear. End the day with a visit to a, from them, suggested barber and you're set.
Also, there is sometimes a principal-agent problem; many personal shoppers work for the stores, and simply buy for you whatever the store is trying to get rid of.
I'm hoping to say "dear fashionoverflow, please pick my clothes for me, email me when you are done. thx." If you say "dear stackoverflow, please do my homework for me, thx", you'll just be flamed.
Stackoverflow is programmers helping programmers, what I want is fashionistas helping nerds.
http://www.jcrew.com/AST/FooterNavigation/personalshopper.js...
In particular, one important thing clothing does is guide the eye of the viewer. Why are graphic tees unprofessional? Because they are distracting to the viewer. Why are suits professional? Because the details--lapels, tie, collar, padded shoulders--naturally bring the eye to the wearer's head, making him the center of attention.
Presentation is important, and affects the perceived content of that which is being presented. It puzzles me that many good programmers understand this about everything except clothing. If one were making a web site, the importance of color coordination would be obvious. Why do programmers so often neglect it when dressing one's very person?
Surely that has to be the easiest way to guide the eye to the head.
The truth is, especially for guys who have a body shape that reflects their sedentary job, nothing makes you look better than a well-fitting suit and a properly knotted tie.
And while the article didn't exactly show the who's who of male models, at least it was remarkably free of the atrocious cheap short-sleeved/khaki cubicle combo.
(If only the Nehru jacket would make its comeback in the western world. I'd finally be able to dress like a Bond villain and get rid of annoying collars in one go.)
* - I am not one of these people. I work best recently bathed and shaved, in fresh clothes and with a clean workspace. Anything less drives me absolutely bonkers.
As a male? Not really. If you can put together a small, simple wardrobe of well-fitting clothes that go well with each other, you'll already be ahead of 90% of other guys, with no on-going time costs other than the normal bathing and shaving duties.
Well-fitting is the important part. Most guys don't wear clothes appropriate for their body type, at least here in the states.