LilDoberman, I'll bet I am older than you, but I still wear the boots I love. OK. So it is no longer the pointy buckle boots I used to wear as a goth in the 1980s, but I continue to love extreme footwear and see no good reason to abandon it any time soon.
Argent, I have some men's skinny jeans and they are my least convincing. I wear them low on the waist and with a belt (but I am used to wearing all my trousers with a belt as I have a teeny tiny waist and not even women's clothes fit it). The tightest I convincingly go is good ol' Primark's slim fit. They are rather like this.
http://cdnarm.yoox.biz/36/36148107WT_lar2_fr.pngAnd, to obliterate the waist, I wear a t shirt that is a size larger than I would normally go so it still looks fitted and not like I am trying to hide in a tent, but without it dipping in noticeably at the waist. I find big shoes/boots also help balance the hips and make them disappear a little.
Oh, and be aware that those slim fitting jeans have a definate magnfying effect. If you wear a packer you will look as though you have a small puppy stuffed down your pants. My cismale partner has a similar pair (a His and His matching wardrobe, how sweet) and it has the same effect on him. I end up just stuffing a sock down there, for decency's sake.