Most Helpful Guy
Alright, first I just want to say there's absolutely NOTHING wrong with doing this. With that being said, I want you to also think about something. Imagine you're having one of those days, go food shopping dressed with sweats and all that. But that day just happens to be the day that a guy you would have loved to date/get to know better is also food shopping.
He sees you. He goes off his first impression of you. What he sees is somebody that doesn't really care about her appearance or the opinion of others in that regards. She's not bad looking, but her lack of effort out in public says that she might be the kind of person you really don't want to approach. After all, when I think about somebody who "doesn't care what others think" there's a certain attitude/personality that also goes with that. A personality that would make me hesitant to outright talk to her.
Now had you gone out looking well dressed, I'm not talking formal event dressed, just comfortably dressed on that line between casual and class, things might go an entirely different way. He sees you. He goes off his first impression of you. He sees somebody who cares about the impression they're sending to other people. What items you wear will send different messages but regardless, he's going to infer that you don't go out in public without putting some forethought into what you're wearing. That says something about self-respect. You respect yourself enough to care about your image. If you don't respect yourself enough to care, others won't either. He also notices you're attractive. You're looks are now standing out for him. He decides to talk to you because all the things he's subconsciously looking out for are going "this girl stands out" and that's what matters. If you don't stand out, there's not motivation for a guy to talk to you over another woman.
That's how we are. Even the confident ones who are willing to strike up a conversation and make the first move. We can't go out of our way to talk to every mildly attractive woman we see. For starters that would just be too much. And second, we pick and choose our battles. We pick the women that stand out to us. If we're going to put our time and ego on the line, we're going to go for the woman that stands out.
But forget relationships entirely. What if you run into a co-worker? Or your boss? People do remember those things. It wouldn't be the end of the world, but if those same people saw you looking like somebody who knows how to dress for the situation, that is also going to stick in their memory. "Clothes make the man. Naked people have little or no influence on society."- Mark Twain. That quote means that if people judge you based on looks, which EVERYBODY does, and 90% of your body is covered in clothes...what do you think people base their first impression on? What you wear.
Do what makes you happy, but just keep in mind of what "consequences" there may be as a result.
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