The idea of "how a pipe looks on me" is alien. It's like a carpenter buying a hammer based on how it looks in his hand. I also don't care what people think of my looks. I have a girl who thinks I look great.
Now...you put me in a room with some really nice, old fashioned flannels? Like Woolrich flannels that are thick and warm? Yeah. That's my fashion statement right there.
I wear either $10 Walmart junk shoes or $300 Redwing work boots. Neither for fashion, of course, but practicality. It's the same with pipes.