I wear the same thing everyday. All the time.
I have EIGHT shirts that are exactly the same. Short sleeve henleys. Green body, grey sleeves. I search this shirt out on Poshmark and ebay. Whenever I find one, I buy it.
I also have about 10 pairs of pants that are exactly the same. They are black. They are actually lounge pants, but they don't look like lounge pants. They are really sharp looking. They have a nice crease, and I've had all of them professionally hemmed. Since I don't tuck my shirt in, they look like dress pants. Very high quality.
I have about 14 pairs of wild socks. All striped, each pair in the same pattern, only they are different colors.
I almost never wear anything different than the above. When I go to a doctors appointment and have to "dress up", I simply wear these clothes with some dress shoes.
Sometimes a friend will say "Didn't you have those clothes on the last time I saw you? I always say no.
There is one exception though.
The "kitchen shirt" and the "kitchen sneakers".
I remodeled my kichen about 4 years ago. Took me 10 months. I got attached to a different green shirt at the time, as well as a pair of Adidas sneakers. I wore them almost every day. This shirt and shoes represent an accomplishment for me, so I refuse to give them up. I'll wear this shirt about once every two weeks. It is so threadbare, that you can clearly see my nipples and the outline of my navel. The best part of the shirt is the number of holes it has in it. Big holes. There are so many holes that it doesn't look like a shirt anymore. It takes me about 10 minutes to figure out how to put it on because I usually mistake a regular hole in it for the hole your head goes through.
I mow the lawn in the sneakers. They have essentially disintegrated to the point where it feels like I am barefoot. They are hard to walk in. The outer edge of the left one has an 8 inch by 2 inch hole in it and my foot just blows out the side of the sneaker when I walk.
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The only difference is that when I am not at a job, I wear tour shirts, mostly, and sometimes shirts I got from a favorite woodworker of mine. I also had a drawing of mine, no matter how horrible I am at drawing, made into a tee shirt and one hoodie.
People ask me the same question about wearing the same thing. I was vindicated one day when someone else said, nope, those pants are clean. I asked how they knew. There was a fabric softener they spotted just then, hanging out one of my pants legs, 
I didn't even notice it was there. It was morning. I hate morning time. I am surprised my paint shirt (It was college, so I wore a plain shirt there) wasn't inside out....again. That same semester, another student told me my shirt was on inside out. I did not even know. I hate mornings, like I said.
I have numerous pairs of the cargo pants and numerous tee shirts, including some duplicates that I didn't realize I already had. I have had some of the tour shirts since the 1990s and 2000s but because I rarely leave the house, I rarely wear shirts. They stay newer longer. I hate wearing shirts. That is why I like the soft cotton tee shirts. For anything I have to leave the house for, like work or classes, which I still take from time to time just because I like to, I wear a plain tee shirt. I don't like to start conversations based on what I am wearing in those settings. I'd rather get done what I have to get done so I can get back to my part of my life I like, where I am home alone or with friends.
People are so surprising. 
