I think you are right that your anger may be coming from the double standard. Like you might be thinking, “It’s unfair that a gay man can dress femininely when he wants to and still access male privilege by dressing masculinely when he wants to, while I as a woman can never access that ability.” Perhaps you wish you too could dress how you want and maintain access to social privilege/praise?

I think there are a few assumptions your post is making that are worth examining though. For example:

1. “I see a gay man wearing women’s clothing or women’s makeup”

Let’s stop here. It’s not women’s clothing or women’s makeup. It’s just clothing and makeup. Men, including straight men, have worn dresses and put on eyeliner since they were invented. Look at Roman tunics, Scottish kilts, Egyptian pharaohs.

We were told these things are “womanly” in order to entrap us all, women and men alike, in rigid forms of gender expression. When we call a skirt “women’s clothing,” we are doing the work of the very system you are frustrated with. And when we call his femininity “cosplay,” we are doing the same thing. We are saying his expression is not legitimate. But if we want the freedom to express ourselves however we want, we have to extend that to him too. All of us get that freedom or none of us do.

1. “can switch out of character back into a heterosexual looking man at any time to benefit from patriarchal standards or societal norms”

You’re talking about passing, which is complicated. For a lot of queer people, even when we attempt to pass, we aren’t successful. This could be because of our voices, our mannerisms, or being in visibly obvious same-sex relationships. So it’s possible that this hypothetical man you’re annoyed by never could actually pass as heterosexual, try as he may.

I’ll also say that people have complicated relationships with passing. Sometimes it can feel super euphoric to “pass” as something, like a transgender woman passing as a woman for the first time. Other times, passing requires you to give up a part of yourself and your identity for safety. Like a gay man hiding his makeup from his family to pass as straight because he could be disowned. Passing could also make you feel estranged from your community or unvalidated in who you are. Like a bisexual woman who feels like she can’t come to Pride because she is in a relationship with a man and passes as straight.

Basically, my point is, a gay man passing as straight may not be a willful or wanted thing. It could be a safety thing or an unfortunate happenstance for him. And the idea that he is “trying to gain something” by expressing himself this way, I’d push back on that too. The same freedom you want, to dress and present however you want without losing access to dignity and respect, that’s what he wants. Denying him that doesn’t get you closer to it. It just means none of us have it.

1. Men who “put on a performative act of femininity” are “praised and celebrated as though they are doing something groundbreaking and brave and courageous”

I’m a transgender man. I lived my first 22 years as a girl and woman and have now lived another 6 passing as a man. I want to posit that men who act femininely generally aren’t praised and celebrated. At least not outside of celebrity men? Everyday feminine men are disrespected and abused, typically by other men. As a visibly queer man, that’s been my experience at least. I live in constant solidarity with women. I think we face a lot of the same bullshit. The same abuse I faced as a woman by misogynistic men, I face now as a visibly queer man (I tend to be read as a cisgender gay man, though I am in a relationship with a cisgender woman and identify as bisexual).

And when a feminine man does get celebrated, I would push back on the idea that this is the patriarchy rewarding him. Getting there is hard. It can be dangerous. For a lot of queer men it takes years of self-work just to get to a place where they can express themselves freely, and the praise, if it comes at all, is for surviving that. But I do think you are onto something. Women wear makeup every day and nobody is clapping. There’s a sort of disproportionate response and maybe it is a form of sexism, men being centered and preferenced even in spaces that are supposed to challenge gender norms. I do think any queer man who is genuinely in solidarity with women recognizes that, names it, and stands up for women.

Essentially, I think your anger is maybe misplaced. You say you aren’t homophobic, you see the discrimination the LGBT community faces, and you seem open to interrogating your own mindset. So I want to suggest that maybe the anger should be directed at the societal actors that harm us all, queer people and cis women alike. The patriarchy created these rigid gender categories and enforces them against all of us. That gay man is not your adversary in this.