Besides the pat answers of being wealthy (good health, the love of friends and family, etc). I think wealthy or well off is being able to afford what I want/need without having to over analyze the purchase. Some examples: I keep my home at 69-70 in the summer months (May to August) running the a/c 24/7 because it feels more comfortable and I can afford it. Having said that, it isn't something I do on May 1st, it is when the days are getting uncomfortably hot and the nights are 74+ all night. It is the same in the winter, I keep the heater at 71 because that is comfortable for me and the family. But we could bump to 80 if we wanted.
If I have to fly, which is rarely, I pay 'extra' for a direct flight and don't even entertain the thought of getting the less expensive flight that might have a plane change and layover because I can afford it and it is worth the convenience. I plan on flying 1st class when we retire for more room, but it won't be every month, it would be when we feel the need to travel.
I think going out to eat in general is kind of extravagant, I don't have a problem with going to Denny's, IHOP, or Sizzler. How can you mess up eggs, hash browns or bacon. DW does prefer IHOP's pancakes to Denny's though. I know what I am getting at Sizzler and don't order steak there, because it is usually a cheap cut of meat and chewy. If I want a better meal I will spring for a filet at Outback or better steakhouse. Ruth Chris'? - maybe, if their steak is that much better than Outback, etc. It is kind of relative, if we were eating at IHOP and similarly priced eateries then we would go out to eat a few times a week, 3 to 4. If we were eating at outback then it would be 1 or 2 times just because I know of the price differences. Sometimes I feel that Sizzler is within $10-15 of Outback then I would rather go to Outback
Can afford a decent middle of the road car, not the base model tinny feel of the cheaper Hyundai, KIA, or even Toyota yaris. Splurge for the solid feeling Tundra vs the Tacoma, have some upgrades that I can use. I don't have to get a Lexus RX because the Toyota Highlander is built on the same platform, etc. etc.
Haagan Daz, Ben and Jerry's or Tillamok for good ice cream. Going to the grocery store and just buying what I need to stock up the house without looking at prices or keeping a running total (like when we were poor college students). I always try the store brand because I like to save money, but if I don't like the Kroger gravy, I will spring for McCormick. I don't clip coupons, but I will take any discounts the store offers or what they send me in the mail due to my shopping habits.
I have noticed when talking to some co-workers about a new product I have tasted or used and sometimes they will ask, 'how much was it' (like a new salsa that I got at Costco) and I reply I don't know or didn't look, I will get comments like, "I wish I could not look at the price". That is wealth to me.
Then of course there is the ultra wealthy, to me that is more than two houses (which home should we stay at this month, Reginald?), multiple high end cars(Mercedes, bmw, Porsche) , own private jet, yacht, etc.