In my experience, both are cool.
I like to go shopping in a pretty skirt and top ensemble, so that, if I see a dress I want to try on, I don’t have to faff about with zips or any of that nonsense.
The tops usually have a relatively low neck to make it easier to get off over the wig.
I also carry a pair of heels in a tote bag to get a better idea of what the dress will look like dolled up.
Going out for the evening is a different matter – I have an addiction to sequined dresses.
I’ve tried ballgowns, cocktail dresses, flapper dresses, all sorts, but always seem to end up in a short sequined dress. I feel so happy and sparkly in one, and it’s a great conversation opener – you can guarantee being approached and complimented on the dress, and take the conversation anywhere that feels good.
One night I wore my most daring costume ever, but it had no sequins: It was Burns night last year, and I wore a white, see-through peasant blouse with a black full cup, lacy bra underneath, over the knee black socks with flamingos on (I like flamingos, and they ought to be Scottish, because they look such proud birds!), cute black Mary Jane shoes with 2″ heels – and the tiniest Tartan kilt. Not one of those silly tight ones, a proper, flare, pleated, heavy wool kilt that was only just long enough to cover my pristine, gleaming, silky white knickers (if there’s a chance they’re going to show, make sure they’re worth seeing – an ex-girlfriend who loved short skirts told me that).
A gay guy came up to me and admired my outfit enthusiastically just a few moments after I left the hotel, and the evening continued in that vein!
People love seeing other people who have made an effort to create a striking, yet tasteful image – so yes, sometimes it’s great to stand out.
But if you’re going to stand out, be outstanding!