It happened in stages, so I'll just give the timeline...
Early-to-mid Teens (Denial/repression phase):
-Grew my hair out a bit.
Late Teens (Nearing the end of the denial and repression phase):
-Grew my hair to shoulder-length.
-Occasionally wore hair-clips and bobby-pins.
-Pierced my ears.
-Experimented with eyeliner.
Early 20's (End of repression, beginning of acceptance):
-Bought some 'secret' girl clothes, dressed in drag/wore more make-up (sometimes).
-Came out to all my friends (past and present)
Mid-20's (Got stuck in a rut and stalled):
-Joined various games and virtual worlds and created female characters/avatars. Though in 'the real world' my transition was put on hold, I gained some social experiences online and started my first relationship identifying as trans.
-Bought a few girly/androgynous clothes for boy-mode.
-Bought a small light-blue 'travel-bag' that I used as a purse.
-Came out to my sisters.
26 (Got out of my rut and started seriously transitioning):
-'Feminized' some items, like cell-phone cover, tablet skin, deodorant, got some perfume, etc. etc.
-Came out to my parents.
-Found a therapist.
27 (Hittin' the fast-track.

)
-Got my letter after 4-5 months.
-Found an endocrinologist that was willing to work with me.
-Got my prescriptions filled (E and P). Blood work done.
-First laser session.
-Second endo visit, upped my E dosage and added Spiro. Got new prescriptions filled.
-Had a big talk with my parents, which reaffirmed their support and has made me relax around them more and now I'm able to talk with them about what I'm going through.
-Submitted paperwork to expunge my (minor) criminal record.
-Filled out paperwork for a legal name change. Action on that is pending the results of my expunged record.
Roughly that order, and so many more changes ahead!

But yeah, these are all changes I either naturally made or I had to muster up the courage and motivation to deal with and initiate. If anyone reading this is thinking about transitioning, know that it really takes a lot of willpower and commitment to get everything done! So worth it though!