At first it was to join the masses in being my favorite character. But also I chose what costume would be easy to find pieces of and build, as opposed to sewing since I can't sew. I love to build and create things, blame legos on that, which expanded into drawing, and then costume building. At first, I thought Kumoricon was the only place to wear your character's clothes without being ridiculed for it. But then I discovered the forums had people organizing meetups. And so my first successful cosplay was at the rose festival picnic in 2008 at waterfront village. Since then, I've built other cosplays and attended meetups, not just for fun, but to test fire and ask others what I could do to make my cosplays better for the conventions.
Fortune and courage had smiled upon me again over the spring to fall last year when I got a job from Sherwood's Play-N-Trade, to cosplay as Captain America. To hold an arrow sign on a nearby street corner and bring the customers in. But even that costume had some flaws that I with my constructive mind, wanted to tune up and customize to work better. I've found that my unique design behind my outfits is that they're mostly made from everyday clothes in the right combination, and so they're meant to withstand the rigors of weather and travel.
Other than the one time when I worked, I always feel nervous cosplaying in public alone without a group. Though when I cosplay as a pirate and battle down at the park with my LARP Amtgard chapter, I do walk to the local store, and from home to the park and back by myself. I don't feel nervous then, just alone.
And yes, like most male cosplayers at some point, I dreamed of making a character cosplay that could reel in a hundred fangirls, a chance to be admired, and reap the rewards that would follow. A dream which has diminished over time for many reasons, but never faded. Popularity at a con is a good thing, but not the only thing. It's a privilege not to be demanded and expected of.
So for the fun of building, the fun of being in character, and the fun of being a mascot to the fans and their icons. That is my reason to cosplay. What's yours?