[DISCUSSION] Dressing outside comfort zones

I know this may not be so much of a discussion(although it can be) but it's just a problem that I've been facing and would like help with​So I have many inspo on how I'd like to dress and the styles that I like but generally...people are pretty closed up on it. From where I live(SG), I feel that people generally dress pretty conservatively yknow tshirt, flannel, skinny jeans. Nothing wrong with that, of course. It's a look that works and will always work but to me, I'm really obsessed with clothing and I'd love to dress differently.​For example, in the recent year I've switched over to the oversized look and I love it and I thought people would too but yknow that's what I hoped. I'm too skinny, oversized isn't nice. You look like you're homeless with that oversized clothing.​Bought an Adibreak Track pants(my first real baggy bottoms) and I've rly been messing with it and all I got from my friends were "what are you wearing?" and honestly if you were to tell me they're just jealous I don't think they are i mean they all dress well and all(maybe not all of them) and tbh i dont think ppl generally have time to be jealous over clothes lol​Even my girlfriend every piece of clothing i've showed her, she'll break it to me nicely i guess by saying its just not her style but hearing it for a year i've kinda gotten numb to it. the only place i really feel good is when i dress to go school where nobody i hang out with goes there (only a few) and nobody really judges me lol.​I composed a look where I throw an oversized guess tee over white button up with skinny black ripped jeans i thought it was dope but literally zero ppl shared my views. just got a bit bummed out. maybe i just dont look as good as i thought i would in those clothing and they were right​just wondering how do you guys dress outside of ur comfort zones? because i rly dig the fits over on here, but it'll probably be seen as a tryhard over where i am :/ via /r/streetwear https://ift.tt/2PftCvO