When I was tying flies commercially, there was local fellow who purchased flies from me occasionally for trips. He stopped by the house once to pick up some flies, and his attire was IMO, quite appropriate for a day out on the bay fishing. Otherwise, he looked like a bum!
His clothes were badly wrinkled, and there was a few stains, & obvious wear. He however looked very comfortable!
This fellow owns a very large local real estate business & is a very rich man, a multi-millionaire who can afford anything he wishes to wear.
Great guy, avid fly angler too! His attire had nothing to do with anything except it was what he was comfortable in wearing. I've seen him in his business attire, and he's a sharp dresser!
Once in a local tackle shop, one I supplied with flies at the time, the owner pointed out an older fellow who was browsing some terminal tackle. He looked like a typical hard working fellow who could have been anyone in the area. Faded & worn jeans, an old worn flannel shirt & a worn hat. This man was also a very rich man. A local contracting legend who had built one of the most well designed communities in the area & who's work had a huge impact on the Inner Harbor area in Baltimore. He could also afford to wear anything he wanted.
Clothing or gear does not always tell the whole story. As the saying goes, never judge a book by it's cover!
I make a point to never try to judge anyone by their appearance, especially when it comes to fishing attire.