If fashion means what the kids and twenty-somethings of today look like, in tight jeans from their sister's closet and long, unwashed hair in their eyes, day-glo sneakers and ratty old t-shirts, well, I'm out. In warmer weather I wear Carhartt carpenter shorts (which are short, not to the knee baggies but an appropriate, above the knee inseam) with a t-shirt and in cooler weather, Wrangler jeans. I wear the same kind of sneakers (black New Balance 473) all year long, or ankle length lightweight hiking shoes. I might add a favorite long sleeve flannel or chamois shirt in cooler weather. I always wear the same t-shirt, the Duluth Trading Longtail Tee, of which I have twenty, all black.
Yes, my wife is exasperated with my wardrobe.
I carry IWB, 4-5 0'clock strongside, and never forget it's there. I have yet to need to carry in a suit, or business casual, but when I do, I'll adapt.
By the way, fashion is fleeting but true style is forever. I've worn the same get-up with little variation for twenty odd years so I suppose as un-stylish as it might be, it's mine.