I'll share my secret. Rather than trying to initiate a conversation with others, make it easy to initiate a conversation with you.

I started wearing hats outdoors to keep the sun off my balding head (I've had a sunburn up there, and I don't want another one), and the hat I had around to wear was from when I went as Ash Ketchum for Halloween. Or even just looking at my hat and smiling...

Nearly everywhere I go with that hat, I'll get someone saying nice hat, or professing their love for Pokemon, or asking me if I've caught them all.

This provides an opportunity for conversation and a shared interest. I can ask them if they're into the show, the books, the card game, the video games. How did they get started? What Pokemon is their favorite? Who's the best trainer? When did they start liking Jesse and James? Do they like old stuff or new stuff (I've got the OG hat from season 1).

It takes almost no effort to wear a hat and it helps me use my social skills when I'm out and about. And keeps the sun off my face a bit, and is handy for napping at conventions. You don't have to be Ash Ketchum, any character hat will do.

Also, bonus secret. When I'm sleep deprived, I get chatty... You may or may not, but if you do, use it for practice when it happens... and if you say something embarassing, you can always blame the lack of sleep. I was just at First Robotics worlds and the setup is harsh for sleep hygiene, but I had a ton of nice conversations with random robot people. Shared interest, opportunities and sleep deprivation combined. Otoh, much fewer notices of my hat at the convention center than I expected.