Made popular by Americana work wear, made available by Daiki Suzuki via Engineered Garments and Woolrich Woolen Mills and made awesome by great Japanese styling. While a lot of us have grown with more traditional 'fits' of slim pants, denim, jackets and shirting, there is something extremely appealing in the aesthetic conducted by some of Japan's designers and stylists which page homage to some classic Americana pieces. The baggy work pants, loose fitting blazer, wool vests, big knotted ties and more often than not, some great boots. A great example can be found in the last two Engineered Garments look books. It is however a slightly tough transition from a slim, well fitted outfit, to either incorporate some of these pieces or go all the way into the 'anti-fit'. I personally really like the look and have been doing a more slow incorporation with a couple items. It's been a common topic with a couple friends lately so I thought I should touch on the subject. When done right, there isn't much better, but doing it right isn't a particularly easy task unless you're buying full EG collections and happen to be aesthetically blessed.
I think the keys are cohesive materials, tonal colors, use of wools and the footwear and how the pants hit the shoe. Of course these are general points but any of them done right or wrong can make or break the entire look.