NEED COSPLAY IDEAS! And other stuff, too...

I mentioned in my first post that my first anime convention is coming up in January. I am quite excited for it, but I am also stuck with a big dilemma.

Who should I cosplay as?

My situation is this... I'm a guy, yet most of my favorite characters are girls. I might consider crossplay, but I'm afraid others might be weirded out:/ But the truth is, there are really only a few male characters I would be willing to go as. Top of the list are Archie of Team Aqua and Giovanni of Team Rocket.

Now, if I wanted to crossplay, my options open up a little:
Leaf/Blue (Pokemon)
Akari Kamigishi & Kotone Himekawa (To Heart)
Nanaka Yatsushiro (Myself; Yourself)
Haruka Nogizaka (Nogizaka Haruka no Himitsu)
Karen (Sister Princess)
Sakura Kinomoto (Cardcaptor Sakura)

Of these, I feel Leaf/Blue would be easiest. But I need suggestions from y'all. Who should I cosplay as? Is crossplay a good idea? Or should I just go as is? You can click on the second banner in the header (the purple one) to be directed to a list of anime I've watched on MyAnimeList. Please, don't suggest characters in shows I'm not familiar with. Thanks for your help.

Now the random stuff:
My dad's birthday is today. His age? That's a secret :P

I don't know why I'm mentioning this since you've already seen it, but I've got a new blog header banner! Further customizations to come...

That's it. HIT ME WITH YOUR COSPLAY IDEAS!

Oh yeah, free cookies for whoever can guess the model year of the LeSabre in my blog header :P

Buy Zorro's hat and cape, buy the staff online and modify the hat... you get a Sir Aaron costume ^^

LEAF! This is a Pokemon forum, so...

Crossplay is only non-creepy if you've got a naturally soft complexion and a relative lack of facial hair. (neither of which I have. :P)

If you can indeed crossplay, I vote for Leaf/Blue...whatever her real name is. XD

Otherwise, I'd love to see someone cosplaying as Archie...I"ve never seen that before. XD

I also vote for Archie to cosplay. Would love to see that. :P

I dare you to go as Dawn. >:0

I think Giovanni would be cool, and just a random stab, but should be close, '83ish

Leaf: 2
Archie: 2
Giovanni: 1
Dawn: 1
Sir Aaron: 1

Looks like Leaf and Archie are gonna have a face-off XD

And the LeSabre in the header banner is a 1985 model. I keep my cookies.