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does it hurts you through your socks? looks like they can possibly cause irritation?
Anchors are best if the laces aren't bulky/non-compressable, and that your shoe tongue is big and padded enough to reliably cover both eyelets. An Anchor sits flat against the eyelet to remain low-profile and reduce chafing, but it's possible depending on how far up the eyelets are. Do a cursory check on your shoes while wearing them before considering also the possibility of relacing them.
I have yet to wear them on a pair of shoes where they cause discomfort. Even on shoes where the eyelets are not covered. I use them on Nike frees, Converse, and Vans which does not have a padded tongue. Maybe Andy and the Massdrop team can chime in to how they feel on the Converse as they had the chance to try them out.
We tested them out and they sit flush against the side of your shoe. I was running on the treadmill with Adidas Sambas + ankle socks and I didn't feel any irritation.