Yes, it very much happens to us.
We travel internationally (pre covid) about 4 months a year. Sometimes longer. We travel with carry on only and we are spontaneous travelers.
We can be happy at a no star chalet on an island in Thailand, in a six star resort, or a cruise ship.
We do carry on only because we can find ourselves climbing two or three flights of stairs in a European B&B or climbing over moored ferry boats or climbing in and out of long tail boat in Thailand, or have the valet insist on taking our bag in a luxury hotel or resort.
Clearly, our selection of clothing is limited. No extras. That means on a cruise or high end hotel we are always casual. Shorts or dockers. We pass on the formal night (do not like them anyway). We also avoid those people who seem to want to judge us by what our occupations were prior to retirement. I mean really, who cares. Or they want to regale us with how important their children are or how well they are doing. We do not care.
This really varies by nationality of those we meet.
At one point one seven month trip we met a couple who seemed shocked that we were homeless simply because we had sold our home and placed everything in storage for a year. I could see in their faces that they could not understand how we could even be on this high end cruise. The other question was so did you sell your home in order to pay for your travel.
Some very strange responses except from the growing number of early retirees who are doing exactly what we are doing. We have met some wonderful friends along the way who we visit in Australia from time to time. But the bottom line.....NO we simply could care less what other people think. We are long past that on our life's journey. We view that concern as a complete waste of time and effort.
We also now live on a cul de sac. Most of our neighbors are early retirees. Usually two late model vehicles, often Acuras, Lexus, Mercs, etc. in the drive.
We have a 2006 Accord and a 2007 Solara convertable. Do we care? No? Do we feel that we need to keep up? Absolutely not. Especially when we are out of town so often during the year.