Luxury that is distinguishable is about impressing people (especially people who can't afford the item). Indistinguishable luxury is about impressing yourself.
Is this correlated to low self-esteem or a touch of arriviste/imposter syndrome? Probably.
I've seen it argued that that's a much more effective way to enjoy money: rather than making drastic changes to your lifestyle, just make every little thing you do that little bit nicer.
I remember my friend getting an internship at <MegaCorp> on about £15k for the year (totally tax free). While he was on that wage he refused to pay less than £30 for a t-shirt, whilst I would expect at least 2 or 3 t-shirts for that price.
When I was learning to play guitar (self-taught), I had the expected hard time. I didn't know what I was doing. So, sometimes, when something went wrong, I was inclined to blame the instrument. I mean, I'd only paid $200 for this guitar, amp, headphones, etc., in one package. They can't be any good, right?
When that guitar broke, I still wasn't any good at guitar, but I went out and bought myself a Les Paul. Les Pauls are expensive guitars but, most importantly, they're used by people who play guitar for a living and are taken on tours and all that jazz. I paid for the privilege of not having an excuse to blame the instrument any more. It's more guitar than I'll likely ever need.
Now, when I do something wrong, I at least know that the fault is mine and not the instrument. (Yes, I know it's a poor craftsman what blames his tools, but I was indeed a poor craftsman, and didn't know any better.)
I suspect it's the same thing with bikes, jeans, etc. You're buying a better quality product because it's better, and gives you a sense of satisfaction that you won't have to worry about a loose thread on those jeans, or a squeaky chain on that bike. You're rich, so it doesn't matter that it costs 10x the cost of the next best bike, and is probably only 2x better.
"Wearing a coat thought to be a doctor’s may improve attention." http://www.nytimes.com/2012/04/03/science/clothes-and-self-p...
"I wear a 1.2k jean and ride a 20k bike. I justify my success"