Hi there @MrBig2015!
I’m not a crossdresser, so afraid I can’t comment on experience or fit for example, but what I would say is have a think about what fabrics you like the feel of and what style you’d like to achieve. You can then have a look at photos and what you think would suit you/you’d like to wear. I think a lot of the fun is in the experimenting so if you think it looks nice, go for it! I’d normally suggest going to shops and just looking round, seeing the outfits, asking for advice from the shop assistants etc, but that may be quite tricky in current times! Hopefully someone else will be able to advise on sizes etc that may be suitable.
With make up, it depends what you’ve got and what sort of look you like. For example, natural/fresh, full face, nudes/colourful. Watching YouTube videos for makeup tutorials can be super helpful if you’re new to it. Happy to try and help if you have any specific make up questions or advice or certain products?