I get lots of dorfs with one sock or two socks on one foot if I say "socks", but they wear a sock on each foot if I put socks twice.
My civilian armor experiment worked great. New migrants show up, I disable miners/woodcutters/hunters, set up the new squad, with this uniform:
leather armor
leather leggings
leather low boot
leather low boot
sock
sock
shield
shield
Then I unschedule everything, remove all supplies, and activate long enough for them to gear up, then deactivate. No bad thoughts from the draft, extra survivability in case of random attacks, and no bad thoughts from worn clothing!
Though now I'm picturing a bunch of hairy little men running around dressed like S&M fetishists... which is unfortunate.
I do socks because I still get random cloth and it seems to keep them happier, tracking sock supplies is way easier than full clothing as well.
Oh, regarding exact matches, mail shirt+breastplate never has any problems with me, they always wear both immediately after I activate them. I highly recommend using exact gearing for your main military dorfs, as the civvy uniforms lead to lots of swapping armor as new stuff is produced and the "higher ranking" civvy dorfs will do the "grab the best armor for the slot" stuff, leaving periodic explosions of leather armor laying around.