"At first it were overwhelming, and I started out small. Something trivial at first, something that wont make a huge impact on the way I dressed. Yet.
Boxers."
Actually.. underwear was the about the last article of men's clothing that I bought.
I had been wearing boy's/men's desert boots starting in junior high... though I'm wondering if cost might have had anything to do with it as back then it was very common for boys items to be much less expensive than those for girls.
After high school, I started buying men's jeans when I discovered that not only did they fit me better, they didn't have to be cut off and hemmed - ALL women's jeans and slacks are apparently made for 6' tall customers. Except for one pair which I wore only 3 or 4 times and then ended up giving to my Mother, I haven't worn a pair of women's jeans since.
I ended up in a job where dress was jeans (or work slacks), steel-toed boots and uniform shirts, ballcaps and jackets or coats. This just made things even easier for me, giving me an excuse to buy socks and t-shirts out of the men's department.
Eventually, I started buying men's shirts, jackets, sweats, sneakers - you name it. I was pretty well dressed head-to-toe in men's outer wear before I finally bought any underwear.
LOL... no one can see your skivvies, yet I was more scared to be caught in a pair of jockey shorts than to be seen fully outfitted in men's wear. I wished I had bought them sooner though, as I discovered that they were cooler, a million times more absorbent, and not itchy. They don't creep up places you don't want them, and of course - no flowers and butterflies and bows and crap.