What is a bootleg cut? Here it means a broad flare at the bottom of jeans to accommodate western boots. Regardless of the definition, I strongly recommend ignoring all trends in suits. I order my suits today much the same way I did a dozen years ago and am therefore happy with any suit I pull out of the closet. Suits were done evolving in the 30s and 40s. I strongly recommend you hunt for some of the Esquire or Apparal Arts illustrations, which ran through the 50s, and you will see what I mean. There is very little from that series that I wouldn't wear today, and I don't pretend to dress in period clothes.