I hope you don't mind me answering this from a GG's POV.
I think what you're missing is that most of us GGs don't feel as if we are being judged by others when we go about our daily business. If you just look around, you'll see women dressed casually with minimal makeup, if they're even wearing any. They feel comfortable in who they are.
It's true that everyone enjoys seeing a beautiful and well-put together person (male or female), but that's just the cherry on top of the sundae. Most of us do judge others based on their demeanor, what they say, their body language, their actions, basically who we perceive they are inside. Not on how they look. Little things like fashion or makeup are inconsequential, really, in our day to day lives. It's not to say that when a woman dresses up for an outing, she doesn't care about her appearance, and if she is competing with other women for men's attention she might have a glance or two in their direction to check out the competition. But, most of the time she does go about her daily business just like everyone else.
I think it is CDers, more than anyone else, who place such a priority on looks and have such a critical eye for what others are wearing. And this does makes sense because CDs are constantly taking notes to see what they are missing, to determine how they can pass in a gender different than assigned at birth. And perhaps in the process, in order to feel better about themselves, some CDs (not all) get into the habit of comparing themselves to GGs who do not place such a priority on their looks.
Well, I suppose there are some non-CDs, namely small segments of people who also form opinions of others based on what they have and this extends to how they look, but for the most part, if I look around at all the people I interact with in my daily life, I do not feel judged by others based on my appearance.
Does any of this make sense to you?If you feel evaluated, it is perhaps not on a scale of makeup or fashion expertise, but maybe it is more about people trying to understand why a GM would want to dress as a GG. You and I, and the people in our community understand all of this, but people in the mainstream don't. My SO and I go out together dressed frequently, and she always presents and dresses beautifully. But, if we are stared at, I believe it is because she has been read and people are just trying to understand who they are seeing. They are not evaluating her makeup, her nails, her jewelry, or her choice of sweater, shoes, or dress, as a CDer would.
Maybe this is why many TSs cease to place so much importance on their looks. They've altered their appearance with HRT, electrolysis, perhaps FFS, so they begin to feel comfortable in not looking like men even with nothing on, and this gives them the confidence to just be who they are without so much emphasis on fashion and makeup?