I'm really at the start of transition, and for years I've always been wearing womens' sneakers etc, and some girls jeans that are not too tight where my dangley bits dangle. I've always had good excuses because my feet are size 38.5 and my waist is 26.5" which means mens trousers cannot be found for my size in the Netherlands, and mens' shoe sizes usually start from size 41, and my socks have always been womens (show size again). I've often worn girls' jewelery and jackets so no issues there. I don't wear women's underwear being I see little difference between mens and womens, because they do similar jobs, except bras.
And I wear this in work and out of work and with family and friends, and I've always looks a little gay/camp/girly without HRT. I have no idea what'll happen if I present as female, because I have not been that close since I was a teenager with makeup and long crimped dyed hair and long fringes. I'm 40 now and still sometimes have strange glances if I walk around, and I don't mind ( except when they won't stop staring), because I really cannot imagine anybody would not mistake me for a man!
So, yes, I am slowly changing the way I dress., but there are not lots to change! Funnily we went shopping for winter boots on Saturday and I had chosen a pretty cool pair of ankle high women's sneakers, and my wife tsuggested a really obvious pair of women's calf length leather boots with 2" heels and asked if I liked them because she thought they'd suite me, and I was taken by surprise ( we were in a women's only show shop ). A nice surprise I add.
So, step by step, and then the switch.