Something that is “old school” is old-fashioned in some way. It could be an old clothing style reworn in a new way, or an old procedure or method of getting work done. Being “old school” could be negative or very positive (even trendy) depending on the context. A teacher using “old school ways” would be likely represented in a negative context as being unchanging or not adapting to modern ways. But a rebuilt old school car from the 70’s would look really fashionable and cool.
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