From
http://www.xbox360achievements.org/forum/showthread.php?t=109141
Miner (Stone Quarry)
Lumberjack (Forest)
Carrier (Trained to carry goods for you)
Wool Harvester (Sheep, Sheers are found to the west of town center, embedded in a forest)
Crystal Harvester (Crystals, Rod found southeast of town, surrounded by Stone Quarries)
Primary School Student (Kefling placed in Primary School)
Secondary School Student (Kefling placed in Secondary School)
Guild Kelfing (Kefling placed in Guildhall)
Mayor (Kefling placed in Town Hall)
Lord (Mayor placed in Keep)
King (Lord placed in Castle)
Artist (After creating an Artist's Plaza, select it and choose a color to get a Kefling with the hat)
*NOTE: Artist Hat tends to glitch. If you are positive that you have all the hats but still aren't getting that achievement, select you Artist's Plaza and a color again. This hat seems to reset after each game reboot.