Hooked side up on the board, so I can scratch my itchy toe whilst playing barefooted.
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Who cares which what round you stick it! Just think yourself lucky you can buy a ready made, modern age miracle like Velcro to start with. Back when I was a lad we had to make our own Velcro like material with matted sheep's wool as the fuzzy side and shark skin as the hooky side. Plus we had to sheer the sheep and then catch and skin the shark first!

Might be worth making a thread about. I haven't seen any on here for a good while... or this
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Here's my thought process with anything velcro, FWIW. The non-moving part (ie, the board in this case) gets the loop part, because the hook part is way more prone to gathering hair/dustballs/etc and so on, so I want the stationary part to collect less hair/dustballs/etc. The hook can go on the part that gets removed/replaced/swapped. But that's just me.