a half dozen in my 20s and 30s....I think I have passed that part of my life and started with self-acceptance...

I've done it a couple times though it was mostly due to huge fluctuations of weight and I don't have much to wear since most of those clothes I still have are male clothes from when I was 243 right before HRT earlier this year, now I'm 179. I do plan once I get money to throw it all out and only get gender appropriate clothes from now on, the estrogen is certainly making the dysphoria that much worse whenever I have to see myself wearing m ale clothes >_<

Never had to purge... mom did a great job of that for me. It was more like, how many items were you successful in holding on to.

I have purged a few times on my own due to being caught by my wife, but the last time I was caught, she took it upon herself to purge everything. She was super upset at finding my clothes and stuff, and got even more upset when she saw how many pretty heels I owned. I am now starting to rebuild the wardrobe again, hopefully with better luck.

Only purged once. when I went full time. Did the purge a bit hasty though sins I only had two outfits left all good now though.

If you want an estimate, maybe around 10 times, and I'm 64 years old.
I have not started transition quite yet, since I am working on the blessing of my wife.
However, I am in the middle of a slow purge right now. The good kind. I am slowly but surely getting rid of all male clothing. I still have some, but I donate or discard up to 5 male items per week whereas I purchase up to 5 female items per week.

I'm in the progress of the first one. Gotten rid of one item here and one there over the last 6 months. I've gotten attached to a lot of it over the years, so I'm taking my time to gradually pare it down. Also prefer to see items that are in good condition go to charities instead of the trash.

I remember secretly crossdressing a lot after puberty started. Then I stopped when I went to an all boys high school.
One crossdressing period in college that lasted a couple months which ended when I made a mistake and was certain I was going to be discovered.
Started crossdressing again at age 40 and never purged.  But I did slowly move everything into a black trash bag I kept in the basement.  That was when I was at the "If I can't live as a woman, then I don't want to wear her clothes" stage.
Then in 2013 I was in suicidal crisis (my 3rd).  At my darkest time I did a complete purge.  After I got help and started feeling better I started crossdressing again.
I can draw a direct line from that crisis to where I live today.

Only once and it was mainly because I did such a poor job shopping for clothes online at the beginning.

I've never purged and thought it was curious at first until reading reasons why people would do this.

When first purchasing clothing I didn't have much to spend so those purchases were well thought out and meant to last. Never thought about tossing them but did go through periods that I would not dress.

More times than I care to remember.  I carried so much guilt for more than 45 years (I've known since I was about 5 or 6 & am 51 now).  Early on while single, I would buy then feel so bad, purge and wait a few months then repeat.  I came out to my wife this past summer and she told me to stop throwing stuff away.  Now, I have space in my closet and dresser drawers as "Paula's" wardrobe is being developed...next step, let Paula step out.
Paula

Three times for feminine clothes.  One partial purge so far of masculine clothes.  One more of those still to come.

I've never purged feminine clothes, but I refused to wear masculine clothes, ever since mom allowed me to dress myself. I always dressed androgynously. I discovered flowery Hawaiian shirts, cute, feminine and nobody ever gave be a hard time about it. I own over 250 of them.