Infovore, do you know anyone who has the sort of look you’re aiming for? I have simply asked friends things like “How did you get your lips so well-defined?”, “How do you make your eyebrows look so well-defined without being overdone?”, “What foundation are you wearing?”, etc. Pretty sure that’s less intimidating than walking into a department store, and if you want someone to actually show you, you can always ask them “Can you show me how to contour my face?” or something.
Personally, I learned a lot about makeup from books. (I know you said you want to learn from hands-on experience, but I’m just saying this in case someone else has the same question and is reading this.) I bought books that had a lot of pictures of different looks achieved with makeup – Kevyn Aucoin, Ray Morris, and Robert Jones are three makeup artists that have some books out like this. This was helpful because I got to see how different products achieved a different look. I saw how liquid blush looked different from powder blush, or how liquid eyeliner looked different from pencil liner. How dark eyeshadow just in the crease of the eyelid gave a different look from dark eyeshadow over the whole eyelid, how dark eyes paired with dark lips set a different mood from dark eyes with light lips, which colors paired well with which skin tones. It’s not the best way to learn techniques, but it’s a fabulous way to understand how to use different colors and textures to create different looks.