Well, I'll post my story.
I've got a problem when it comes to cosplaying: I'm black. I've got very few options if I want to be an accurate cosplayer, and most of the characters I don't like or I've never heard of them. ....<snip>
I'd say don't worry about race / skin color. I asked my Japanese exchange students and they said that they feel that nearly all anime characters are Japanese (there are a few characters in some shows that declare that they are not Japanese, but all the rest are considered Japanese).
So, given that about 98+% of Kumoricon attendees are decidedly NOT Japanese, it means NONE of us are the "correct race" for the characters. So pick a character you like and go for it. The Japanese choose the very pale skin color for the characters because that's the color they have traditionally used in their artwork for skin color - despite the fact that it's not even close to actual skin color of the average Japanese person. It's art - they can do that. (This is likely because they want to increase the contrast between the skin color and the character's clothing, features, etc. This is also why many anime characters have non-natural hair colors - it's easier to tell which character is which)
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As for gaining confidence in cosplaying, here are a few tips:
* Don't start with a costume that is totally different from your usual clothing - if you normally don't wear revealing clothing, then you'll feel uncomfortable walking around in something that's just barely more than a bikini. There are even some characters that wear ordinary-looking clothing with a few "quirks" that makes them recognizable (but only by those who have seen the anime... I call that "stealth cosplay" because when you wear it outside of convention, no one notices, but when you arrive at Kumoricon, everyone addresses you by the character's name).
* SMILE
You'll be amazed how far that gets you.
* Wear comfortable shoes - yes, your character wears 6" heels, but can YOU walk around in those all day? Probably not. Bring footwear you can walk in comfortably. You can always carry the stilettos in a bag and wear them only for photoshoots.
* Think about what you'll be doing during the day - the chairs in all of the rooms are wool, and lots of others (some unwashed) have sat on them. Do you REALLY want to have a skirt so short that you have bare skin on the seat? (ewwwwww)
* Remember - cosplay is just interesting / different clothing. Yes people will stare at you on the train, but I bet they're thinking "cool clothes!"
* There will always be mean people. Ignore them. The rest of us think you look awesome.
* If you want help improving your cosplay, ask for advice from cosplayers who have done it for a long time
* Cosplay is supposed to be fun - it's "Costume Play"...