After sending her details about my problems and the kinds of styles I admired, the stylist experience was very old-school retail — a department store — but she was unexpectedly pragmatic, giving great advice about picking durable clothes and materials that specifically fit well on me, with lots of wink-and-nudge budget advice (like "This would look great on you for $50 less" followed by flashing me a Nordstrom Rack or Poshmark listing of it).
Also, finding out that the department store has a complimentary tailoring service for hemming and adjusting the waistline on pants you buy from there permanently changed my clothes shopping process.