P.s. that first shirt is simply for hunting. Look up Woolrich hunting shirts for the red and black. The orange is a common hunting colour for safety. Wear it with the brown brogues or some boots with denim at the hunt camp or the folk music festival. It could be a sexy lumberjack shirt only in the correct context.
Not to advertise a business, but the website grailed.com is a user to user marketplace (don't think the creator takes a cut) for men's clothing with both designer brands and a "Basic" version of the site with cheap brands. There's a lot of lightly worn stuff so if you can figure out sizing, this is a great place to barter and dress really well for cheap. View it on a full computer monitor.