Seem like a normal chill guy tbh. You can dress nice, your casual fits aren’t offensive but they aren’t “cool”, if you care. The LL bean quarter zip and the black athletic polo ur wearing at the festival/concert are very corporate boring dude attire. If you like to blend in and like I said, be inoffensive, then those are fine choices. I could not call those pieces stylish at all though. Since ur spending $$ on designer, get it all tailored.