A couple of things have to be in place...
1) You have to have skin downloads set to on. Which you appear to have.
2) The server you're on has to have skin downloads also set to on. If the server does not have this feature enabled skins will not be downloaded regardless of what your individual setting is.
Assuming those two items have been met, then the server has to trickle download each custom skin to each player. This has to be done without significantly compromising the network performance (i.e. increase the latency or ping time). Each skin is 1.00 MB in size, however, multiply an entire server full of custom skins that have to be downloaded for each player and you can have a lot of data flying around. Particularly in a dogfight server scenario where you could see twice as many players over the course of an hour (some joining and some leaving).
This is a long winded way of saying that it will take time for custom skins to propagate.
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