The kind of person who is an "expert" at retail fashion isn't going to be working at the price point I have in mind.
That being said, I'd like to have better clothes for special occasions / dates / events. I would totally pay someone to pick stuff out for me. Not for everyday clothes, but for those special outfits.
I wouldn't go full Steve Jobs and only wear black turtlenecks and dorky sneakers, but a closet full of OBDs & polos seems reasonable. I would definitely try someone's recommendations, but only up to a fixed dollar limit (like $200~300). I would be prepared to bag it all up and donate it if I didn't like it.
Shirts, jeans, sweaters, anything... they're all over the place in terms of fit.
With shirts, you've got different torso widths, lengths, arm hole sizes (I don't know the word), depths and widths of the neck hole. A slim fit, an athletic fit, a relaxed fit, will all vary from brand to brand.
With jeans, same thing.
Then you've got the fabric and stitching. I'm not sure I'd buy clothes online. Too many variables.
I mail you a list of measurements. You mail me a list of brands and styles that fit.
Like for example, 32-waist Wrangler seems to be equivalent to 30-waist Gap. Only way I know this is because I tried on the jeans at the mall and found those to be the most comfortable on me.
The variation is strange and it's not just pants but also shoes sizes aren't consistent between brands either. I think the way Zappos solves this is they send you the shoes and you send them back if they don't fit well.
There would need to be some brand research done, checking the fitting and sizing of various brands, so you could know that "with a 31 inch waist, measured around the navel, I would fit in 30 inch Gap jeans and 32 inch Wranglers."
That trip to try on those two pairs of jeans cost you what, an hour? two hours?
I would definitely let someone do it for me. I don't know a lot about fashion and I'd love to look better.
My shopping is 50/50 in-store and online, when I do in-store shopping I like to have my wife with me, mostly for company and to verify what I pick fits and looks good.
spoiler: I'm an engineer and I work there.