The platitude holds that you can’t teach an old dog new tricks, but there’s a 200-year-old mill in Scotland that strongly disagrees. In fact, it seems that more and more designers, mills, bootmakers and tailors—most of them founded more than 100 years ago—are re-inventing themselves, toying with innovations and trying to shed off at least part of the fustiness that comes with being so well established. After a century and a half of reliable service, a shoemaker might understandably want to try something a little new and a little daring. From Harris Tweed to Allen Edmonds, TIME looks at 10 established menswear brands who are casting old traditions in a modern light.