It happens allot but at the moment not so much as we are making direct to retail (apart from wholesale to Japan) so we have a sense of freedom in terms of design/resources but at a low key small level.
First step..learn at a brand large or small that can offer you experince you can then use later.
Myself? i am quite narrow i wear my own clothes and a very limited selection from others...Save Khaki chino's,RRL Jeans,Crockett & Jones/Alden shoes..and i love really technical outwear..its not that i am so arrogant i don't like other brands i am just influenced by other things.
That's very very difficult...one that many friends always name check ( one in the archive but i don't have one as i will soon re-make better!) is the double Harrington made in Italy around 2000 which is two jackets that button together but can exist as two separate jackets.