"Richest Looking" Areas

[ProgressiveModerate]

This is an interesting question. Reminds me of San Fransisco where many upper-middle-class and wealthy neighborhoods look almost like something in a 3rd world countries.

Wealthiest looking can be a bit subjective, especially depending on whether you're viewing it through the lens of old or new money.

From my experience the wealthiest looking areas are usually high-end vacation areas with high concentrations of second homes. Because many of these are second homes, the true extent of the wealth may not be captured by census stats and stuff.

Parts of the Hamptons, Nantucket MA or Aspen CO fit this vibe. I think what helps is these places all have coherent vibes and in the case of Colorado mountain resorts the vibes is heavily enhanced by natural beauty.

I'd also argue many parts of Manhattan just because of seeing all the large corporate glass office buildings.

There’s definitely a lot of flashy sort of wealth in the Miami area but to me it all feels very cheap and you often have situations where it’s only in small pockets and not consistent and a lot of it still feels somewhat cheap to me

I'll have to sleep on this question a bit though.