I am Abe Burmeister, founder of Outlier, I accidentally built a clothing company. AMA
Five years ago I was a freelance graphic designer who was looking for a better pair of pants. I never found them. Eventually I realized I'd have to just make them myself. So I went into New York's Garment District and figured it out, I made a better pair of pants and wore them every day. Eventually I started wondering if maybe other people would want a pair too so I put them up on the internet and voila, people bought them. So we made some more and started designing even better product. Five years later Outlier is a real company, fully bootstrapped, mildly profitable and has 12 employees.
Obviously it took a lot more effort than that sounds, but in a lot of ways it was easy because the clothing industry left so many doors open. They were way late to the web and more concerned with keeping their old ways in place than figuring out how selling online could make things better. They also spent way too much time figuring out how to make things as cheap as possible, rather than how to make them as good as possible at the fairest possible price. That's the theory at least and so far it's seemed to work.
EDIT: Done for now, but I'm likely drop by from time to time if anyone wants to add some extra questions.