It depends on the individual - if you take someone with a great personality and this man is very well known, you could almost assume that everyone will laugh when he wears a cheerleader uniform.
If it's the "Average Joe" - dress to express not to impress. Rather than buying a $3,000 tux aim for a more casual look. If you are shopping at the salvation army, try out a wholesale store like "Ross".
- By dressing "overboard" or expensive : you look like a try-hard (which takes you down a notch)
- By dressing "under" or cheap : You look like a wanna-be (which takes you down a notch)
Dress like you would dress yourself, you don't need peoples' thoughts or opinions (especially mom's). Go out there and be who you are. If the girl can't accept you, she is missing out.
Beauty is difficult to hide, expecially with clothing. Personally I like plain white t-shirts. They're usually soft and fall across a guys shoulders and chest nicely. Honestly, do you think a gorgeous girl with her hair a bit messed up in comfy pajama bottoms is ugly? NO! She actually looks more attractive because she appears more 'human' like you and she's not even trying to be hot - she just IS! Same applies for guys. We see much more beauty that what you see when you look in the mirror. :)
I don't think it matters that much as long as you put some effort into it. For example, my ex ALWAYS wore sweats, and I didn't notice it right away but it started to bother me after a while. They're more comfortable so I understand if a guy wears them sometimes, but every day is excessive. On the other hand, I dated him, so it wasn't a huge turn off. He would've looked better in jeans or something else though.
I'm not sure what you mean by "cheap" pants, but I don't think the cost of your clothes matters much. My current boyfriend could afford all the designer brands if he wanted to, but just sticks to Levi's and casual t-shirts he likes and it looks great on him.
it won't make you ugly if your already attractive, but you won't look as good and you will have less appeal
I was just talking about this with some of my friends. To be honest, style does count! I've seen tons of attractive men who just don't know how to put on clothes. I mean a plain t shirt and jeans is cute, but if your wearing something extremely clashing and out of date then not many people will want to go to know you. If you want someone to get to want you, you have to at least dress decent so they won't be embarrassed to be out in public with you. Yknow what I mean?