Is calling someone "old school"- offensive/derogatory? [closed]

My colleague, a relatively young school teacher, prefers not to use e-mails. He is digitally absent.

During a recent teacher's meeting, while I appreciated his efforts towards content development, I also called him "old school". (associating a sense of pride in being Old School)

I can tell, the comment has made a difference, our relation has dived south.

• Is calling someone "old school"- offending/derogatory?

The safest answer is: Yes. There is a very strong derogatory flavour often associated with the noun-as-adjective. According to this article from The Age:

To say something is "old school" has become a pejorative [usage]. It implies out-of-date thinking.

This association is not guaranteed to be assumed by a listener or intended by a speaker, but the term should only be used with great caution, carefully thought out contextualisation.

If one includes the views of the former Google Dictionary, the situation with connotations is seen to be bipolar:

old school: used, usually approvingly, to refer to someone or something that is old-fashioned or traditional.

But better safe than sorry (and I suspect that a younger audience might rather assume the pejorative nuance).

I once complimented a speaker on the way he communicated in such an acceptable, gentle (though not weak) manner. It's hard to give compliments without sounding mushy or patronising (I find). However, my 'You're an expert at hedging' wasn't exactly the best way I could have phrased it.

It could be taken either way, or as a neutral, matter-of-fact description, depending on context:

Urban Dictionary:

Anything that is from an earlier era and looked upon with high regard or respect. Can be used to refer to music, clothing, language, or anything really.

Client: We have three PC's running MS-Dos 6.
Consultant: Shi'...that's old school.

Oxford Dictionaries

Used, usually approvingly, to refer to someone or something that is old-fashioned or traditional:

amenities that my parents, being of the old school, still take for granted'

The Online Slang Dictionary

Old. Used when describing something you remember from a long time ago like in the 80's or early 90s.

To do something in a way that is more in line with traditional technique/style rather than modern or progressive style

Old fashioned, out of style, uncool. Opposite of "new school," which is hip, with it, in fashion.

The old school is any group of people who are traditionalists: they do things the way they've been done in the past.

It’s a term with pride woven around it.

• However, considering the situation- the teacher's meeting- the young guy did not buy your compliment.

When someone calls themselves "old school", it usually means something positive. It means that they consider themselves diligent, conscientious, and honest in contrast to the perceived tendency of the younger generation to avoid hard work and to find an "easy way out." When you call somebody else "old school", the possibility of offensiveness depends on the context, specifically whether you said something positive or negative about them. Some examples - You could say: "Your handwriting is excellent-you're old school!" and that would be a compliment. Or you could say: "You don't know how to use current technology-you're old school." That would be offensive. Some relationship advice: Why don't you tell your colleague what specifically you want him to do? So instead of telling him that "there's something wrong with him" for not using digital communication technology, tell him that "the school needs this report and that response in computer form because those are the guidelines, thanks for your understanding. We'll be happy to help if you need help with this and that software."