I know many people lease cars which saves a ton of $ on the monthly side.
The guy that lives across the street from me makes pretty good money (not as much as me + Mrs Dex), but he lives in a house worth 80k more, had 2 NEW Mercedes, just bought a new 5th wheel camper, etc. and his wife stays home with their 3yr old. Turns out the company that he works for pays for one of the cars, he leases the other (low miles since it stays home with his wife), the company paid a HUGE relocation fee (essentially his down payment).
Another guy down the street works from home, has the biggest/most expensive house on the block, drives a Corvette, wife drives an Escalade, just dropped $40k cash to finish his basement, his wife doesn't work, he has an autistic son, and he pays cash for everything. He is just really smart with his money and he uses the system. The Vette was bought used from some old guy who never drove it, wife got the Escalade because some drunk driver ran a light and hit her so they cleaned him out, the county provides "assistance" because his son is disabled.
Sometimes it just comes down to the "luck of the draw" with employers, family situations, investment timing, etc. But I think more often than not, they are up to their eyeballs in debt with no financial planning for the future.