My earlier response was fueled by emotion and sleep deprivation, which isn't super helpful. On a more rational note -
-I spent $25 on a barber cut (it felt important to do just once), and $7 buying beer in a fit of trying to be cool and male afterward in the grocery store across the street. Plus $4 getting something for my kid, because she knows if I ever get alcohol I'm going to feel guilty and so buy her a treat as well.
-I spent close to $10 on deodorant and body wash.
-I spent $8 getting a pair of shoes, after haunting the closest thrift store for awhile until they stocked a pair of male sneakers that fit me.
-I spent $2 on underwear at that same store (it's not icky I swear).
-I spent $30 on a binder (underworks 997), and then it got torn up through stupid circumstances.
-I spent $5 on shipping for a binder (underworks 983 I think) from a charity organization.
-I spent $30 for a mooncup (regretting that now) because too many times I felt nervous or ashamed after tampons became visible while I was digging through pockets or my backpack.
-I've spent ~ $100 in food stamps to supply and reimburse a friend for watching my daughter so I can occasionally go to trans support groups and events.
-I spent ~ $7 on used sports bras, because regular bras make me dysphoric.
-I spent ~ $35 on a harness and smallish dildo (both on clearance sale) so I can have more of the sexual options a normal man has.
-I spent $10 to see Kate Bornstein speak (it was sliding scale and I could've paid nothing, but my daughter started telling the folks who were tabling that we're poor we barely pay rent we never get to eat at restaurants my mom can't pay you, and my pride was so pierced by that that I puffed up and casually handed over the suggested donation).
-I've spent at least $40 on books about gender that my library doesn't carry.
-I pay $5 a session for therapy, sometimes. They know exactly how I live, and are often cool with letting me keep the money for happier pursuits.
I'm not on T, haven't had top surgery, haven't changed my name, haven't gotten my uterus taken out, and I don't own any ties or a nice razor. Plenty expense ahead.
Also, I wish there was a way for all of us to count the ways we spend money to maintain sanity in the face of a situation that seems pretty cosmically unfair and that society shuns us for.