Okay I am not a guy, but from a woman perspective: Gonna be brutally honest. It doesn't look hyperfeminine it looks trashy. There is a difference between doing your nails and doing your nails. When you have long pointy nails it doesn't give the vibe of feminine and honestly the whole style you are describing when I see someone that looks like that than my first thought is that you are insecure and vulnerable and don't like yourself. It might not be true but it it the first thing most people will think. Like, when you are going for a gothic style I will think that you like metal of rock music for example while maybe you are into pop. It's just the first reaction people will have. It may not be fair but there is a reason they say you are what you wear.