/fa/ - Fashion

I dress like shit and want to change it.

So basically, I BMX, so a majority of my clothes (80%) are beat to hell vans high-tops, band tees, and BMX brand clothing. I just moved to Boston a little under a year and it seems like everyone I work with + know seems a little more well, put together.
I used to own a pair or two of jordans back in HS, but it seems that the whole style scene has changed. And I need help.

Current wardrobe
American eagle/no name flannels
Hardcore band t-shirts
Like 4 or 5 pairs of jeans?
Ripped up/vans that lost their shape
Windbreakers from BMX Companies (Cult, Kink, ETHIK)
Fucking military BDUs (but I draw on the back so they're a little custom).
BMX Brand dad caps, polo dad caps, trucker caps

I'm looking to get a couple neutral pieces where I could build out some good outfits for work, days I'm not biking, dates, etc. Just so I don't look like a huge sack of shit.
I really like earthy colors like brown, black, olive and cream. But wouldn't know where to start. Ideally, I'd be looking for 1 decent pair of shoes (I was thinking like Flyknit 4.0s in black), maybe 3 pairs of pants, 5 tees and maybe a few hats? That way I could swap them out and make a few outfits.

Price range: I'm a developer so I make a decent amount, so I guess these would be the max prices for each of the outfit pieces:
Hat - $20-30
Shirts - $25
Pants - $40-50
Shoes - Maybe $175
Jacket - Maybe $75 - 100
I'm also a pretty slender dude, about 6ft tall, 150lbs.
Thanks for any of the direction you guys can give me, really appreciate it!

TL:DR; I dress like shit, hook a brother up with some ideas to help me get started in streetwear fashion.

pic related: some ideas of what I'm looking for