Is this the new hatless thing, or is one of the hats his headset?
In Source SDK, i loaded up scout.mdl, and in the tab next to 'Sequences' (I forget what it's called), i clicked the model drop-down list and saw three choices 'scout', 'hat' and 'headset', scout is the normal scout, hat gets rid of the hat, and headset, i dunno, i didn't try that, but i think it gets rid of the hat? You need to turn Normal Mapping off then back on to make the changes otherwise it'll stay the same for some odd reason
You can do this to the ragdolls in Gmod by placing one of the TF2 ragdolls and typing this in the console 'ent_fire !picker setbodygroup #', with out the 's and # can be replaced with a 0 for a normal appearence, 1 for hatless (Spy masks for the Spy though), and i think that's it