How do I do it?

When i was 13/14 i would always be wearing skirts and dresses and be fully confident in them. However when i got older with bulling at school and issues with weight. I stopped and now only wear them for special occasions and then they have to touch the floor. Now i am 21 and feel more secure in myself and feel good about my body.
I wanted advice on how to start getting back into wearing them. I don't want to jump straight in with mini skirts but gradually work up to it.
I have just started wearing cropped tops again now i have my belly button pierced. But want to know where to start with dresses and skirts.
I have thick thighs and a bigger ass but smaller tits so anything that works with this would be perfect.
How do I do it?
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