When would you say someone is Englander and when say he's English?
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There is no common situation where you would expect to use 'Englander' to denote an English person. There are of course, 'New Englanders' but they are from a different place altogether!
One might deploy 'Englander' as part of the term 'Little Englander', defined in the OED as a noun meaning:
Chiefly depreciative. An opponent of an active international policy or role for England (in effect for Britain), originally (now hist.) with regard to the British Empire; (now also) spec. an opponent of England's (or Britain's) active involvement in or membership of the European Union (or its predecessors).
1962 Hudson Rev. 15 587 Already there is hardly room on the Continent of Europe for all the..nations, and now that they have begun to roll themselves into one enormous nation,..the feeling in England is that if we don't get in and co-operate we shall simply be buried. There are Little Englanders..who want to keep out.
In this use the person is an advocate of a 'Little England' rather than being an English person of diminutive stature.
The OED also gives an interesting definition of 'Englander' as a stand alone noun (note the parts I have bolded):
A native or inhabitant of England (also †Britain); (occasionally) one with nationalist views. Cf. Englisher n. 1, Britisher n.
Not used as a self-designation by the English.
I note that you phrased the question ‘when would you say someone is Englander’ rather than ‘when would you say someone is an Englander’. In the limited contexts where the word might be used, it is always a noun, never an adjective.
The two options would be "John is an Englander" or "John is English".
As @Max Williams says the first option is not used nowadays, despite being in the dictionary.
However it is used for other locations, eg. "Cathy's a die-hard New Yorker". This is common and acceptable. Of course the difference here may be due to referring to a city or region versus a nationality.
As a side note, from a literary perspective, when you say some one is a something-er you are associating that person with characteristics of that location, as opposed to just attributing an origin to that person. However sometimes phrases such as "an Englander" are just not used nowadays. It might be used in the past though, in the recent movie "Murder On The Orient Express" an American character refers to another character as a "Britisher", which I thought was interesting.
Engländer is, the German word for English people.
However, Englander is not used on its own in English. That doesn't mean it doesn't exist. The expression New Englander does exist:
someone from New England
So yes, Englander is used as part of New Englander, but not for people from England, but rather from a part of North America.