I have black Thorogoods and brown Red Wing mocs. I usually wear them with black, or blue straight jeans cuffed a little above where the break would be. Besides denim a wider leg millitary cut olive pant, or Carhartts sometimes cuffed sometimes not. As for tops I don’t really think about it too much. Sweaters, flannels, t shirts, hoodies, button downs, denim jackets all work well. A felt or wool jacket will definitely work.