Questions: Fashion & Beauty

True story: I started wearing glasses at age six. They weren't cool, they weren't pretty and they were definitely not comfortable. I hated wearing them and would take them off whenever my parents and teachers would look away. But! 23 years passed and at one point glasses became a chic and sexy accessory.

From 4 styles, which looks the sexiest on girls?

So I want a pair of Timberlands (the tan 6" pair that a lot of people have). I'm 6' and very skinny (for an American lmao)
I asked my mom for a pair and she said they were too "ghetto". Are they really tho? Yes I am white, I listen to rap music, I'm also sort of a sneakerhead, so you could say I'm not a "white boy". But im not white trash. I don't say the n word , or talk lik dis my fam what it do uhhh yeah moo dat dopeee. So what I'm trying to say is that I don't want them so i can be "ghetto". I know I'll wear them, and no one will really make fun of you just because they're timberlands. It's a classic model. I know what to wear with them, I'll get good use out of them, and like them. So anyways: main questions A) Are timberlands too "ghetto" for an east coast white male B) Would anyone question me about anything just based off my timberlands C) Where can i find a pair exactly like the one in the picture (mens 6" waterproof timberland waterproof boot) for under retail (so under $190) and D) What do you think of timberland boots? Thanks for reading

I'd like to know your opinion...

Would you say it's Ok for guys to wear tights or leggings or something like that in public? Athletic wear aside, of course lol. I think it would be super comfortable if not for the embarrassment factor! Would you assume they are gay or something? Nobody wants to send the wrong message so it's important to know.

Also, ladies would you date/support a guy doing this? Do you think it's more or less attractive or what?