Many higher end preamps are dated and ugly, why is this?

Dated and ugly?  I think you might mean simplistic with no frills, which I am just fine with.

If Schiit is "pretty" to you, I have to seriously question your taste.

Yeah, Schiit to me is very utilitarian… not attractive. But aesthetics change, they are a social / personal construct. I am an old fart, so I like traditional. The stream punk look of Dan d’ Agosino really offends me. As a group the people that can afford high end audio components we dictate through purchases what manufacturers can sell profitably. My violin red Sonus Faber Amati Traditional speakers sound like I want speakers to sound like and look like… to me, speakers should look like a Stradivarius violin. I value a traditional sophisticated look. I / we will die… the next generation decides what to buy.

Not to mention most power amps……uuggggly! Let there be meters, digital displays, touch screens! Even just a few goshdern LEDs! Now we are talking! Something worth looking at!  Lights camera……action!

I like the look of Schiit stuff, 

Me too

Mike

Beauty is in the eye of the beholder.   One man’s ugly,is another man’s gorgeous.