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Might be age dependant in terms of how it's perceived. I wore otk boots (black suede, chunky heel) with a shortish denim dress and black opaques and my mum (who is late 60s) kindly said I looked like a streetwalker.
To be fair, Little, my DM wouldn't stop at OTK boots to disapprove of my outfits. She pretty much sees anything other than a shapeless Laura Ashley frock from the 1970s as dangerously tarty and confirmation that the world has gone to the dogs.
Fortunately, I stopped listening to her fashion advice years ago and she knows better than to say anything now!