The best example of a fashion startup I've seen is Indochino (www.indochino.com). They were faced with many of these issues and have gone and taken full control of their end to end supply chain. They are selling "physical fucking product" but they are making it more personalized and custom tailored (pardon the pun), direct to the customer. I don't have much need for wearing a suit these days, but the moment I do, the…
As for wanting to learn more, I'm currently teaching a university of reddit course on menswear customs, history, and how tos. Its under menswear 101. Go check it out.