I admit I've felt a tiny bit jealous of people who own something flashy that I've secretly wanted but can't justify buying. But I wouldn't judge the rider. Along with the idea that riding a bike is supposed to be fun, it's also a process. The person who seems unfit for an expensive performance bike today may be training and will become a muscled, speed machine sometime down the road.
I have a custom built road bike that isn't flashy looking at all, but boy is it a joy to ride. I had the wheels custom built, and I believe wheels determine the feel of the ride. I pass my "ballast assisted" friends on descents, which always makes me smile. It was worth every penny.
I also have an Electra Townie cruiser that I bought to have something after knee surgery, the "flat foot" geometry made it safe to ride when my knee was very weak. I assumed I'd sell it later, particularly because it looks like an oversized kid's bike, and, well, I'm a serious rider with the custom bike and all, blah blah... But I really like using for errands and tooling around the MUP trails, where you have to be ready to stop for kids and such. And now I can haul a$$ on the thing, and keeping a good speed on fat tires is pretty good for my fitness.