Specifically, I have shopped with help. I emailed Macy's last week and set up an appointment with one of their "personal shoppers," who ask what you're looking for and try to find it for you. What I was looking for was suits I can wear for job interviews.
The whole thing was relatively painless. We wasted a little bit of time because I misguessed my size, so everything she'd gotten out for me ahead of time was too big. But once we sorted that out, she got me more things, and I tried a bunch of stuff on, and it fit. For values of "fit" that apply to suits, meaning that I will need them altered to shorten the trousers and the jacket sleeves. I expected this, at least for the trousers; it comes of being short but not the shape that people have in mind when they make "petite" garments. So, I will need to find a new tailor in the neighborhood; the one I've used in the past retired a couple of months ago. (The alternative was to have the alterations done there, and wait three weeks or so.) I came home with two fairly conservative pants suits (one black and one gray), and a bright red skirt suit that I may return.
There's a lot to be said for having someone who knows her way around the store, and even has some idea of current styles, going to get me things, rather than having to find them myself; as a bonus, she was allowed to go into the storeroom and get things, when they weren't on display in my size. (I sat and read my book while she went out and found more things for me to try on; she had offered the choice to either sit and rest a few minutes, or go with her.)
This is one of those odd services that is advertised in the sense that the store has signs that say "Macy's by Appointment," but what's not obvious is that it's free. (If you get as far as the web page for the service, it encourages you to "make a free appointment," but if you expected to pay for the service, you might not even look that far.) You pay for the clothes, at whatever the current price is, but there's no charge for the consultant's time and the use of the private dressing room with the nice mirrors. I'm not sure where "knowing that this service exists and is free" falls in terms of class or privilege, but I think telling people that it's there is a good thing. The service is middle-class in terms of clothing prices, and in the sense that the interview clothes they're selling are aimed at middle- to upper-class jobs, but I suspect it could be at least as useful for someone without that background who has decided s/he can afford a couple of hundred dollars for an interview suit.