Male, and I could probably pull it off.
When I'm at work I wear mostly the same outfit every day as it is. A solid-color polo with an undershirt (white or black t-shirt) tucked into a pair of khakis with a black belt and black shoes, and a black leather jacket if it's cold out.
When I'm not at work, I wear mostly the same outfit every day too. Typically a black t-shirt (either solid color or with some kind of logo), a black patrol cap, sunglasses, BDU pants (either woodland camo, Marine digital woodland camo, olive green drab, khaki, or urban camo), a black belt, and black combat boots. If it's cold I'll throw on a hoody or zip-up sweatshirt, a black leather jacket, or if it's particularly cold an olive green M65 field jacket with an inner liner.
I very rarely vary from that, and no one's ever called me out on it. When I was at university I pretty much exclusively wore solid black t-shirts and olive green BDU pants every single day for four years with no problems. My closet looked like what I imagine a cartoon character's closet would look like.