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The main problem I see in dying socks is colorfastness. Because socks get damp, one is likely to experience some "bleed" from a do-it-yourself dying. That's a bit risky inside shoes, especially nice ones with all that absorbent leather.

Then there's the question of how they will come out and whether that shade will be any better. Dying is tricky business when trying to alter an existing color. Besides, it's terribly messy:(

I think I would ask myself just how vital it is to have these socks a different shade of brown (or black?). Most of the time socks are not particularly visible, as trousers cover them except for the occasional exposure when one walks, and while sitting they are mostly invisible under tables or desks.
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