When my friends find out that I write this blog, I usually get a couple very similar responses, one of them being, "oh shoot, this means I probably should dress better when I'm around you."
This cracks me up, and here's why.
People who have tons of information about a particular subject can often engage in some sort of snobbery around that subject. Think wine connoisseurs or coffee enthusiasts. When people find out that this person has this wealth of knowledge, they might get self conscious about their own knowledge on the subject, and start to worry if they're being judged by their ignorance.
I get it, I'm sometimes self conscious about enjoying a crappy wine if I'm with my wine-freak friends. However, unlike a lot of subjects, here are a couple great things about style:
1. There is no true right or wrong. Yeah sure, there are rules you can adhere to, like not wearing the same color denim on your jacket as your pants, or having your suit pants end at a half break instead of dragging on the floor, etc. However, people break these rules all the time, and this includes people who are in the know about fashion inside out. I see well-dressed folk wearing oversized this, or baggy that, on purpose! It's all subjective.
2. The more confidence you have, the more your outfit starts to fade away. Yes, I believe style is important and that's why I continue to write simpler man. However, the one major thing people forget is that style is largely about showcasing you, not just your clothing. You do you, man. As long as you do that, no one will even notice that you're wearing a jacket that doesn't complement your denim very well.
Either way, when it comes to me personally, I have zero expectation of my friends to dress better around me. In fact, when certain friends have a lot to learn about style, I actually get excited, and want to help them if they have any desire to learn more. Knowing that I have information that can potentially help these folks makes me happy.
The only thing that may tick me off is someone's insistence on caring less. People who refuse to learn anything more about dressing better, simply because they think they know it all already, or are too lazy to ever care. Don't be one of those people please.
Anyhow, if you ever come across style bloggers or fashion enthusiasts in the city, don't ever feel self conscious about your outfit. You dressed that way because it's probably a part of who you are, and most people would rather you be more genuine than staged. Doesn't mean don't continue to learn, but just be real. Plus, I may just be wearing some ill-fitting sweats and a nasty T-shirt myself, don't judge.