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Recently purchased two pair of Hey Si Mey loafers, introduced this year. Unlike previous heels of theirs these were disproportionate, see right side 1st image. To correct this I added two additional tips, left side of image. I love the results, the heels no longer look like the leaning tower of Pisa. Better look and I'm sure increased durability. 

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You had to have known when you posted this that your explanation was incomplete. Perhaps this was purposeful in an effort to get some more traffic on here. Soooo.  .  . I will be the first one to take the bait and ask exactly how you accomplished sticking several heel tips together like that. Did you remove the original nails and add a single, longer nail? Please elaborate.

Secondly, and this is not really a question that you can probably answer, but I wonder if the manufacturer got a little lazy or cheaped out on the original heel? Perhaps the original heel, unmodified, would be correct, or at least closer to correct, in my size (USW 9).

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I did cut the nails, Dremmel, then ruffled up the mating surfaces and super glued them.

I mentioned that Hey Si Mey does typically increase heel height with size but for some reason they didn't on these. In your size these may be fine or possible you'd need one added tip thickness. 

I wore the beige pair for 12hrs straight yesterday with no ill effects.

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I purchased replacement tips that were nearly perfect. Your idea may work well although not sure if nailing would be doable unless you add some pilot holes just a bit smaller than the nails. These are about .75 inch across and a little more front to back with the full radius at the back.

If you're thinking of getting a pair I'd recommend them. I bought mine through alliexpress. 

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