I get The Look a lot, and I'm not even wealthy yet!
I'm in my late twenties and on my days off I can probably pass for early twenties. I have long blonde hair, no kids in tow and dress casually and without makeup when I can.
When my partner and I were buying a house a few years back, a lot of sales and bank people behaved quite patronizing and sometimes downright mean to me. They thought I was either getting a house from the bank of mum and dad or was taking advantage of a rich husband. In fact it was neither: just hard work from two sides. I was temporarily without a job, but brought in a lot of savings and legal knowledge. As I was between jobs at that point, I was the contact person for the bank during the buying process. They would routinely forward every e-mail I sent to them to my partner to check if he knew what crazy stuff I was asking for this time. Needless to say we switched banks. That first bank also nearly interrogated to find out where the money from our downpayment came from. Savings wasn't an adequate answer. In their mind it was absolutely impossible for two mid-twenties kids who don't even look professional to be able to save one gross yearly income as a downpayment. Since my partner has wild hair and a beard I'm sure they thought it was crime related.
The second bank was very commercial and was only interested in fixing us a mortgage asap. Since we had the knowledge and limited time, this was ideal for us, we just disregarded the bad overall financial advice they gave us. ( A few of those are post-worthy in themselves: like that we definitely needed expensive travel insurance, even if we weren't planning on travelling for a while because we just bought a fixer upper. Because you just might decide to travel tomorrow and then you'll be left without insurance. You can't plan life, it happens to you, so you definitely need to be covered by travel insurance always, just in case).
I'm always conscious that people perceive me as poor because I don't have a car and live in a small house in a 'bad' neighbourhood. The area we live in is actually very convenient for us and not dangerous at all - in fact, even a bike theft is rare. It has a bad reputation because it's a working class neighbourhood, but we were born and bred in areas like these and we feel right at home here. Sometimes we slip up with neighbours though, and get The Look from them, because despite having modest jobs and living in this house, we're not living paycheck to paycheck. We try to avoid showing off that we have money.
Because I live under these circumstances, my boss feels sorry for me and gives me a big raise every year. I need to pretend to him that I really need this job and the yearly pay rise, because he's known to stop giving them once he feels you're financially comfortable. So I don't tell him that I could live off half of my modest paycheck if I had to and invest all the extra money I get from him. My family never knows what to make of our financial situation either. On one hand, they know we're doing all right, because I tell them so they don't have to worry. On the other hand they try to give us things and small sums in cash because they think we're going without. While I like to get used stuff so I don't have to buy new, I don't want them to feel they have to give me anything, because they don't. And they shouldn't take pity on us because we take the train because we choose to.