Gay men love Halloween or as it is often called Gay Christmas or the Gay High Holy Days. We identify with it. That's the myth at least.
It's hard for me to objective on this topic. Halloween is not really my holiday. First, it's not a holiday. And when did it get to be for adults? Don't get me wrong: I love seeing kids in their costumes and I am happy to eat the Fun Size version of anything.
If you're going to do Halloween, do it well. Tossing on a wig, some lipstick, and a stuffed bra does not make a costume. You better work it. Like my friends who host a Halloween party every year. They plan, execute, and spend money and time for months. One year, they transformed their entire house into the Titanic, including having guests 'come a board' on a gang plank to the second-floor deck.
That's the appeal of Halloween: To transform. To be something you are not. To make something different than it was. I like that part. For a lot of guys, Halloween is permission to slip into a pair of heels and venture out in drag -- and that's some straight guys, too. Drag is just a fraction of Halloween, but no matter what you wear or make or how you decorate your house, Halloween makes it easy to be creative and to feel free from criticism while doing it.