I can’t tell you the last time I tried on an article of clothing?
Hell, I can’t even remember the last time I purchased any??
My wife typically just says, I bought you a new pair of work slacks, a new button up or new boxers.
99.9% of my t-shirts are beer shirts, so there’s that.
I do pick out my own hats and shoes...I’m picky about my hats and my J’s
We are the same, but my roommate Jase is the same size as I am or close enough and he loves clothes and looking preppy, so whenever I want to look nice, I just wear his stuff. For her own reasons, my mom insists that I have a double breasted black suit, a light weight brown suit (shoes, belt etc to match) AND a custom fit tuxedo because we go to corporate events where everyone wears a tux.
Dad and I, "Bond, james Bond" when we have our tuxes on which, I'll admit take on really handsome look when they're tailored to your body.
But day to day you and I are the same, HOWEVER, I do one thing that all my friends ultimately appreciate: Every birthday, Christmas AND Valentines Day I buy all of them a 12 pack of black Dickies socks, some boxers, some boxer trunks and some kind of sleepwear/pajamas.
My mom insisted that she know the measurements of all my friends so she could buy them slacks, jeans, dress shirts, ties, and on and on for their Bdays, Christmas and Valentines Day. I was in charge of buying them something more fun like games or whatever.
Her goal was to spend that money so their parents could easily afford a singular or several big gifts and that our gifts didn't outshine their parent's gifts and she'd work with their parents.
And then, there was me, "I don't really want anything" so that's part of the reason she buys other kids so much stuff.
Doesn't an old pair of jeans or whatever just FEEL better than new stuff? It does IMO.