As a former member of the SCA for 10 years, in HOT Riverside, Ca. I can attest to the 'sweating rivers under the bodice' syndrome. I also tried, as much as possible, to stay with period materials and look. However, the proliferation of self-appointed costume police got to be really old. When my husband and I did a lot of the horse games, safety came before historical acuracy. I saw a former SCA Queen get dragged off her horse because her long skirt got tangled with the horses hind legs.
As for pirate garb, I think the vary nature of pirates lends itself to exaggeration and fun. Yeah, be historical when you have to, but roll with it when you don't. I'm making a pirate coat to wear this winter as an every day coat. A major pattern company put out a halloween costume pattern with a Capt. Jack Sparrow look alike on the front. I'd been looking for a pattern of that style coat for a long time, so snagged it when on sale for only 99 cents. Can't wait to whip it up and wear it everywhere.
I just wish there were more pirates and pirate events in my neck of the woods. I loved and miss costumes and taking on a persona, so wearing my pirate coat will have to serve. If someone happens to ask me if I'm a pirate, I'll just point to my truck, which has a window sticker of a skull and crossbones, and says "Pirate Girl.