HOW DARE YOU! You don't get to to judge my nephew! He's braver and smarter then you'll ever know!
And I definitely do not want to hear any sort of talk about how my children all look identical. They are not clones! The technology doesn't even exist!
My best guess is there's an incorrect flag or lack of one on a character template. I've only seen this with Imperial characters, but be good to know if it's an issue with other cultures. Though in my case I'm almost positive it's the result of the empire non-combatant default template. Flags should probably be set to be more sex specific. I'm guessing nobody notices it with females, because male oriented clothing doesn't usually look out of place on a female character. It's only when your son is wearing a dress that the issue becomes obvious.
Code:
<EquipmentRoster id="emp_noncom_template_default"
culture="Culture.empire">
<EquipmentSet civilian="true">
<Equipment slot="Head"
id="Item.head_scarf" />
<Equipment slot="Body"
id="Item.imperial_robes" />
<Equipment slot="Leg"
id="Item.ladys_shoe" />
<Equipment slot="Horse"
id="Item.noble_horse_imperial" />
<Equipment slot="HorseHarness"
id="Item.light_harness" />
</EquipmentSet>
<EquipmentSet civilian="true">
<Equipment slot="Head"
id="Item.headscarf_d" />
<Equipment slot="Body"
id="Item.empire_dress_b" />
<Equipment slot="Leg"
id="Item.ladys_shoe" />
<Equipment slot="Horse"
id="Item.noble_horse_imperial" />
<Equipment slot="HorseHarness"
id="Item.light_harness" />
</EquipmentSet>
<EquipmentSet civilian="true">
<Equipment slot="Head"
id="Item.headscarf_c" />
<Equipment slot="Body"
id="Item.vlandian_dress" />
<Equipment slot="Leg"
id="Item.ladys_shoe" />
<Equipment slot="Cape"
id="Item.scarf" />
<Equipment slot="Horse"
id="Item.noble_horse_imperial" />
<Equipment slot="HorseHarness"
id="Item.light_harness" />
</EquipmentSet>
<Flags IsFemaleTemplate="true"
IsCivilianTemplate="true"
IsNoncombatantTemplate="true"
IsNobleTemplate="true" />
Pretty sure IsNobleTemplate is to blame... that or more serious bug. But there's about 36 equipment rosters flagged for nobles, and I believe new characters like Children and Rebels are assigned gear randomly based on Flags.