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On what sort of occasion would you wear this jacket?

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It looks kind of "90s" to me? I know there was an interval of that decade where black & white houndstooth was trendy.

Ignoring that it could come off as "dated", I can see it with a black turtleneck and black trousers (or jeans). Maybe a black Chelsea boot or similar. It would definitely be "a look".

DH
 
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