The hate for Trek is strong in this forum.
I own 4 Treks, but if it makes me any "cooler"... I may be in the market for a gravel bike soon, particularly a Motobecane (with 105 components) from Bikes Direct. Trek's Boone and Crockett are nice, but I can get more bike for less $ with the Motobecane.
As far as uncool goes... no one brand really offends me. I'm not a fan of comfort or hybrid bikes. Cool bikes in my world are road bikes (with drop bars), gravel/xc bikes, hardtail mountain bikes and fat bikes.