diff --git a/code/modules/mob/living/silicon/robot/robot.dm b/code/modules/mob/living/silicon/robot/robot.dm
index a469bf5258..2173910c26 100644
--- a/code/modules/mob/living/silicon/robot/robot.dm
+++ b/code/modules/mob/living/silicon/robot/robot.dm
@@ -90,7 +90,16 @@
 	/obj/item/clothing/head/wizard,
 	/obj/item/clothing/head/nursehat,
 	/obj/item/clothing/head/sombrero,
-	/obj/item/clothing/head/helmet/chaplain/witchunter_hat)
+	/obj/item/clothing/head/helmet/chaplain/witchunter_hat,
+	/obj/item/clothing/head/soft/, //All baseball caps
+	/obj/item/clothing/head/that, //top hat
+	/obj/item/clothing/head/collectable/tophat, //Not sure where this one is found, but it looks the same so might as well include
+	/obj/item/clothing/mask/bandana/, //All bandanas (which only work in hat mode)
+	/obj/item/clothing/head/fedora,
+	/obj/item/clothing/head/beanie/, //All beanies
+	/obj/item/clothing/ears/headphones,
+	/obj/item/clothing/head/helmet/skull,
+	/obj/item/clothing/head/crown/fancy)
 
 	can_buckle = TRUE
 	buckle_lying = FALSE
diff --git a/code/modules/mob/living/silicon/robot/robot_defense.dm b/code/modules/mob/living/silicon/robot/robot_defense.dm
index 0356c934ff..0a56ea2425 100644
--- a/code/modules/mob/living/silicon/robot/robot_defense.dm
+++ b/code/modules/mob/living/silicon/robot/robot_defense.dm
@@ -1,5 +1,8 @@
 /mob/living/silicon/robot/attackby(obj/item/I, mob/living/user)
 	if(hat_offset != INFINITY && user.a_intent == INTENT_HELP && is_type_in_typecache(I, equippable_hats))
+		if(!(I.slot_flags & ITEM_SLOT_HEAD))
+			to_chat(user, "<span class='warning'>You can't quite fit [I] onto [src]'s head.</span>")
+			return
 		to_chat(user, "<span class='notice'>You begin to place [I] on [src]'s head...</span>")
 		to_chat(src, "<span class='notice'>[user] is placing [I] on your head...</span>")
 		if(do_after(user, 30, target = src))