On the dictionary com. site, the adjective well-off is defined as "having sufficient money for a comfortable living; well-to-do".

At the same time, the adjective well-to-do is defined there as "prosperous; rich" (without mentioning well-off). As for the synonyms of each (1, 2) of the two, although they are almost the same, but there's a slight difference in their relevance for the one or the other.

Does this mean that anything/anyone which/who is well-off is also well-to-do, but not vice versa? Is there a fine difference between the two in usage?

Could there be a situation when the choice was to be made in favor of the one and not of the other?

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    They're both a bit colloquial. The only real difference is that well-to-do is relatively dated / literary, so you should probably avoid it unless you want to sound a bit old-fashioned and "posh". Jul 23 '16 at 19:25

I've been looking through dictionaries trying to corroborate my personal (UK-based) understanding of these terms.

Both certainly imply a degree of prosperity, but neither I think imply that person is very rich; say millionaires not billionaires.

I would agree with FumbleFingers that both are somewhat colloquial, and that well-to-do is rather dated; the biography of P.L.Travers (the author of Mary Poppins) describes her remembering her father as well-to-do.

I have always though of well-off as describing the financial status of a person. The Free Dictionary says moderately rich.

On the other hand I have thought of well-to-do being as much concerned with the outward behaviour arising from that wealth. Such a person not only has money but uses it to buy possessions, often those that increase their social standing.

The Collins dictionary gives this example:

In the seat in front of him a well-to-do matron and her paunchy husband were busy adjusting an expensive camcorder. Pacter, Trudi YELLOW BIRD

Note that the matron (woman) herself is described as well-to-do, and we immediately think of someone very well dressed.

This distinction is not clear in the dictionaries I have consulted, but I do think is implicit in the actual terms themselves. It would not, in my opinion, give the same impression to say

a well-off matron


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