That guy sounds genuine, but it gets weird when the very wealthy decide that dressing like 'regular people' is the style they want to go for. That's when you create a market for $250 pocket t-shirts and $600 denim jeans. Talk about not getting it!
I have been buying $150 jeans most of my adult life and recently read a comment on Reddit that expressed disbelief that someone would pay more than $30 for a pair of jeans.
I'm one of those $30 jeans people. An old girlfriend once convinced me to try on a pair of $200 jeans ("you don't have to buy them, just try them on"). I did it just to shut her up and looked at myself wearing $200 jeans in the mirror. Fit exactly the same, material seemed better quality, stitching was the same, etc. Yes, better. But definitely not $170 better.
Then again, I think Levi's are overpriced these days.
...I assume you weren't surprised when she decided to change her status to your "old" girlfriend.
In other places I've rented I've had absolute arseh*oles for landlords. They wouldn't give you the time of day, but I bet their tenants were quick to move out! (I was)
With that said, not all wealthy people do it.
It makes plenty of sense to spend money to look good when aesthetics aren't your strong suit, but are important to you. People hire landscapers to make their houses look nice and appealing. This is the same thing, but for your body.