Wearing any type of clothes are sometimes funny. Others laugh. Sometimes different marks are available while wearing clothes. What about that? Anyhow have to wear proper dress always.
One thing that I've always found disappointing is when I have to iron a lot. If I had one recommendation about clothing it would be to find a fabric blend that has polyester with the usual cotton. Look for a 60/40 blend of cotton/polyester.
As said, it's not a costume, wear what you want. I wear totally torn jeans and a ripped t-shirt right now. 100% barefoot all the time, have no shoes. Yesterday I got a used zipped hoodie which is really great cause it's getting colder here, but I try to life as minimalist as I can.
Well, make your own? Wear whatever you want. Creativity and freedom are what's important, don't stick to items because you think you ought to. I make and customize my own things, and pretty much anything I own is thrifted and unboring or at least, I think so. Experiment a little with color, have fun, loosen up ^^ I had to laugh out loud at the plaid condom comment. Thanks. Made my evening.
I've now found that you can get shirts that have 98% Cotton and 2% Elastane that won't wrinkle nearly as much as 100% Cotton. Very useful to know because there are way more brands making 98 and 97 percent cotton shirts with the 2 or 3 percent elastane than there are making 60/40 polyester blends. Just thought I'd add that!
Jane thought that my leather shorts were quite cool. Or did she say hot, I can't quite remember. Anyway, she still posts them as our avatar 30 years later. LOL.
That. Polyester doesn't breathe very well. I personally prefer natural materials, but elasthane goes a long way in terms of ironing issues! Also, bamboo makes for pretty damn awesome material when it comes to tees for instance. Very soft, doesn't wrinkle at all, and comfy too. Also a very fast growing resource, which is good. I don't know where you stand in terms of environmental load concerning clothing, OP, but I'd recommend looking into second hand and natural organic stuff for that reason too, not just comfort and aesthetics.
I got hubby some bamboo socks and he loves them. https://www.amazon.com/gp/product/B01LJBTXQA/ref=oh_aui_detailpage_o07_s00?ie=UTF8&psc=1
Flanalette shirts for me. They aren't really "cool" but I find them to be the easiest thing to throw on and do anything in without fears of destroying them. Also let's other people know I really don't think too much of social attire. Slap my boots on and my bootcut jeans and akubra, I'm ready for any event.
I have these yoga pants. Kinda baggy around the ass. Goes well with my flouncy medieval shirt, although that shrunk a bit in the wash to more sensible proportions.