I should've specified whether it was 1956 dollars or 2022 dollars. "Real" means inflation-adjusted. I was thinking of 2022 dollars, so you can't have the automobile.
Were we doing it the other way around, $1000 1956 dollars is only $10,700 2022 dollars. You might be able to get a car for $1k in 1956, but it's going to be strictly worse than a 2022 car--the two things aren't comparable. Which is a large part of my point.
Then I'll take three sets of skirts and dresses (total $30), made of cotton and available in size 16(!) (not a plus size, just, in the regular size lineup!). I'll take a grocery shopping trip, which not only will cost me less than $10 but all of the food will be local and in-season. And I'll take a month of rent in Montreal ($60) to round it out.
If you prefer, I could have blown it all on a single college course, but that seems to belie the idea of a basket. :P
The declining prices are primarily in durable consumer goods, fuel energy, and consumer electronics. Food, healthcare, education, and rent (the things you need to live) have far outpaced "inflation" -- and this is more relevant to the average person because you don't buy a TV every year, but surely you buy bread every week.
That car from 1956 would look cool, assuming everyone else wasn't driving the same thing, but would be objectively worse in almost every way compared to the cars of today.