Will push back here some. Because there is a strong difference between rich, And class, And most people can not tell the difference. 

A tailored suit- Worth it if you know how the suit maker is relevant to you. Did you grow up in an Italian family that knows where they come from? Go there and find the oldest tailor in town and buy a suit. Three of you feel generous. 
Are you someone with your first 100k and know nothing about your family history? Mens wear house. The suit makes the man, But the man needs to know his stuff, Or the suit looks cheap anyway. 

Supercar- Are you planning on track days? Because if not this is basically for having the pick of prostitutes in Miami. You are not impressing anyone with a very expensive toy, You are proving you are “only rich”. Wealthy people drive slow anyway. They do not bother themselves for anyone. The harder you flex the more insecure you look. 

Luxury hotel rooms- Agreed. Especially if it is a historically significant hotel like the Savoy or the Brown. Worth seeing what millionaires lived like 100+ years ago. Being affluent is about knowing where you came from and living to the best of that potential. Corporate hotels are literally all the same- Modern. 

Watch- If you look at it as a collectible. Rich people buy things to consume and wealthy people buy things to keep as assets. You should never wear anything more than a Rolex out in public. Your 40,000$ Lange & Sohn lost 5000$ in value by wearing it once. A Rolex is plenty for the rich person value signal. 

Clothes- Wear what makes you comfortable. It is good to understand formal dress, But it is awkward to overdress. If you don’t work on Wall Street nobody is going to know the difference in what suit you wear and otherwise- And LV and Gucci are perfect tax deductible gifts for prostitutes, So keep that in mind when you give your daughter her first handbag. 

The Mansion- Is it a Virginia or Miami McMansion? A modernist piece of crap that anyone with the money can buy? Or is it a French Chateau? Does your house have character or are you just a rich douche? 

Yacht and Maid- this falls into a certain income bracket. Most people think being a billionaire sounds awesome, But they are actually the most hated people on earth, Thus they live on a boat and answer to no one. That guy did not make his money by being polite to your grandmother waiting in line to buy groceries. They are literally so detestable they need to live on a private boat away from civilians. If you do not understand this you are just rich. 

Fancy food- Italians emphasise the fresh ingredients from the garden. Definitely worth eating fresh food no matter what your income is. Eating cheap takes years off your life unless you are Warren Buffet and Coca-Cola has a vested interest in keeping you alive. Cancer is real. 

Fancy booze- in moderation. I feel like there is a well designed built in cost disincentive to drinking, Just like food. Quality is everything but don’t overpay if you just want to get drunk. If you still drink to get hammered you aren’t even rich. A good scotch or Tequila, A fine wine, Even a decent quality beer is still better than being a cheap drunk. Do your research before you indulge- Kind of the whole premise between being a rich asshole and a refined gentleman. 

All in all remember-The finer things are expensive for good reasons and nobody can survive on just cake. Hard work and patience built every prosperous fortune and everybody bleeds red. The moment you start believing you are better than other people because of your money and status is the moment your wife is fucking her cheap ex boyfriend from high school. Money is a tool not a right. 

Rant over.