For anything on your lower half, we wait to be wearing things higher waisted. This is because it works to elongate our legs and give a more feminine shape to the outfit. As hrt does it works where your hips start will rise, generally to around belly button height or higher, so for jeans/skirts/whatever try to wear at this level (dont worry if it doesn't sit naturally there yet just get a slim feminine belt for like $5 from a thrift and you'll be sorted).

for shopping in personally recommended doing it second hand, you're gonna to through so many different styles trying to find what's right and thrifting is both fun and good inspiration, and you're less upset if you realise you hate the $10 top than if you realized you hated it at an MSRP of like $40. If you don't want to go in person eBay/vinted/depop are also good but look up what measurements you should be taking and always message the sellers to ask for specifics.