The thing that gets me about Harry's disco throwback clothing is that, in the game setting, disco wasn't that long ago. The game is set in '51 and disco was a late 20s-30's phenomenon. Him walking around in flared pants and a green crocodile skin shoes seems quirky to us, the audience, but in the context of the game he's wearing the worst fashion from 25 years ago. Imagine having to talk to the cops and the detective interviewing you is dressed like this:
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