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If I was to see somebody dressed like the people in the above Ralph Lauren clip, I would: a) despise their impeccable attire; b) despise their confidence to dress in a flamboyant outdated manner; and c) despise myself for despising them. :)
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Honestly, I personally love to see people dressed well but for me originality is what makes or breaks a look. I've seen street style looks of people who amazingly look like they've stepped out from another era but at the same time they wouldn't look effortless as they may have looked within that particular time; or they border on appearing contrived.
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