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Don't know how to classify on 1 to 5 scale, but for couple of years I have for 99% of time used 5-6 cm oxfords or ankle boots. Conservative looking with block heels, real leather, great with a dark suit. Maybe cannot call that "heeling" because people just don't notice. Or are already used to my footwear as last time a had male oxfords was in 2013.

Out of office, prefer leggings and wedge heeled trainers. Maybe 6-7cm. Don't use them for running, but returning to car change shoes right after doing stretching. Again, nobody seems to notice. Could be the wetlook leggings that draw the attention ;)

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