[DISCUSSION] I need a major makeover. I'm a 30/M who dresses like a 40+ dad/professor. It's starting to effect my self esteem, and probably negatively effects other areas of my life. How can I fix this?

*I Posted this on MFA too. I figured I'd post it here to get another subreddit's unique perspective. I hope this is allowed.I felt this way for a while but never really took the initiative to get any advice about it. My work requires me to need to wear collared shirts and that has pretty much overtaken my wardrobe. But for the longest time I felt like I come across as a dork/geek, and that I dress like some middle aged dad/professor.I have heard on more than 1 occasion people referencing that I'm "Bill Gates".The type of clothes I always like when I see others wear them is "street wear" I guess. I'm not really interested in looking "smart professional" or whatever it is called. I prefer more urban style if that makes sense. However, I am open to everything.For example, I actually like the deadmau5, graphic t-shirt/jeans skater look even though it's probably frowned upon here. (MFA)I exclusively always wear jeans, and prefer wearing t-shirts when I am able, but for the work week just wear the collared shirts. However, even when I put on a normal t-shirt, I still don't feel like I look "cool" for lack of a better term. I see people while commuting to work, or when watching youtube videos of celebs who wear just simple jeans and a t-shirt and they always look "cooler"and more put together. I can't explain it.In the fall, I , I like to wear long sleeve flannel shirts.I have a few pairs of the same type of jeans, Levi 559. I have tree trunk legs, with huge fat calves. These are the only pair I know of that I feel like I have enough room. A lot of other jeans I try on, are a struggle to put on or take off because they get stuck at my calves area.For shoes I wear charcoal/grey Vans Slip Ons.Like I said above, no matter what I wear though I feel like I still look like a nerd/dork/geek/dad/professor.I also feel like a lot of it has to do with the glasses that I wear and my hair. I almost never style my hair. When I get haircut and have it short, It's easier to style because I can just lift the front up a little and it looks much better, but once it gets to the length I have in my pictures, I don't know what to do with it. These pictures were taken today, and it's been about 5 weeks since my last haircut.I feel like my glasses are outdated looking and I should either ditch them for contacts and/or get a more modern looking pair that fits my face better.It's all starting to negatively affect my self esteem. I never get any attention from women and I feel my style heavily contributes to that. When I am in a group of guys, always feel inferior and like I look the worst. Even when I look at pictures of myself in groups with other guys, I don't feel I fit inMy pictures are at the link below. I included everything I normally wear during the week, and a couple of the long sleeves I wear during Fall/Winter. I also included a couple t-shirts that I wear over the weekend, or whenever I am able.I apologize in advance as the camera on my phone is not the greatest.I'm hoping I can finally find out the truth and get the advice and help that can put me in the right direction.I think it's at the point where I wouldn't be against maybe hiring some university fashion student to go clothes shopping with me. It's something I've considered.https://ift.tt/2LWYSdm via /r/streetwear https://ift.tt/2LKpj9a