diff --git a/code/modules/client/preference/loadout/loadout_hat.dm b/code/modules/client/preference/loadout/loadout_hat.dm
index 82d215e7b4f..4657893bec7 100644
--- a/code/modules/client/preference/loadout/loadout_hat.dm
+++ b/code/modules/client/preference/loadout/loadout_hat.dm
@@ -97,21 +97,21 @@
 	display_name = "cowboy hat"
 	path = /obj/item/clothing/head/cowboyhat
 
-/datum/gear/hat/cowboyhat_brown
-	display_name = "cowboy hat, brown"
-	path = /obj/item/clothing/head/cowboyhat
+/datum/gear/hat/cowboyhat/brown
+	display_name = "cowboy hat, dark brown"
+	path = /obj/item/clothing/head/cowboyhat/darkbrown
 
-/datum/gear/hat/cowboyhat_black
+/datum/gear/hat/cowboyhat/black
 	display_name = "cowboy hat, black"
-	path = /obj/item/clothing/head/cowboyhat_black
+	path = /obj/item/clothing/head/cowboyhat/black
 
-/datum/gear/hat/cowboyhat_white
+/datum/gear/hat/cowboyhat/white
 	display_name = "cowboy hat, white"
-	path = /obj/item/clothing/head/cowboyhat_white
+	path = /obj/item/clothing/head/cowboyhat/white
 
-/datum/gear/hat/cowboyhat_pink
+/datum/gear/hat/cowboyhat/pink
 	display_name = "cowboy hat, pink"
-	path = /obj/item/clothing/head/cowboyhat_pink
+	path = /obj/item/clothing/head/cowboyhat/pink
 
 /datum/gear/hat/pr_beret
 	display_name = "beret, purple"
diff --git a/code/modules/client/preference/loadout/loadout_shoes.dm b/code/modules/client/preference/loadout/loadout_shoes.dm
index f39b25aabf6..89ccd952065 100644
--- a/code/modules/client/preference/loadout/loadout_shoes.dm
+++ b/code/modules/client/preference/loadout/loadout_shoes.dm
@@ -26,21 +26,21 @@
 	path = /obj/item/clothing/shoes/centcom
 
 /datum/gear/shoes/cowboyboots
-	display_name = "cowboy boots"
+	display_name = "cowboy boots, dark brown"
 	cost = 1
 	path = /obj/item/clothing/shoes/cowboyboots
 
 /datum/gear/shoes/cowboyboots_black
 	display_name = "cowboy boots, black"
 	cost = 1
-	path = /obj/item/clothing/shoes/cowboyboots_black
+	path = /obj/item/clothing/shoes/cowboyboots/black
 
-/datum/gear/shoes/cowboyboots_white
+/datum/gear/shoes/cowboyboots/white
 	display_name = "cowboy boots, white"
 	cost = 1
-	path = /obj/item/clothing/shoes/cowboyboots_white
+	path = /obj/item/clothing/shoes/cowboyboots/white
 
-/datum/gear/shoes/cowboyboots_pink
+/datum/gear/shoes/cowboyboots/pink
 	display_name = "cowboy boots, pink"
 	cost = 1
-	path = /obj/item/clothing/shoes/cowboyboots_pink
+	path = /obj/item/clothing/shoes/cowboyboots/pink
diff --git a/code/modules/clothing/head/misc.dm b/code/modules/clothing/head/misc.dm
index ee16f4129c8..e8b6ab50d92 100644
--- a/code/modules/clothing/head/misc.dm
+++ b/code/modules/clothing/head/misc.dm
@@ -188,25 +188,25 @@
 	item_state = "fedora"
 	desc = "There's a new sheriff in town. Pass the whiskey."
 
-/obj/item/clothing/head/cowboyhat_brown
-	name = "cowboy hat"
-	icon_state = "cowboyhat_brown"
-	item_state = "cowboyhat_brown"
+/obj/item/clothing/head/cowboyhat/darkbrown
+	name = "dark brown cowboy hat"
+	icon_state = "cowboyhat_darkbrown"
+	item_state = "cowboyhat_darlbrown"
 	desc = "For the Rancher in us all."
 
-/obj/item/clothing/head/cowboyhat_black
+/obj/item/clothing/head/cowboyhat/black
 	name = "black cowboy hat"
 	icon_state = "cowboyhat_black"
 	item_state = "cowboyhat_black"
 	desc = "This station aint big enough for the two ah' us."
 
-/obj/item/clothing/head/cowboyhat_white
+/obj/item/clothing/head/cowboyhat/white
 	name = "white cowboy hat"
 	icon_state = "cowboyhat_white"
 	item_state = "cowboyhat_white"
 	desc = "Authentic Marshall hair case. Now ya can protect this here homestead. Navy Model not included."
 
-/obj/item/clothing/head/cowboyhat_pink
+/obj/item/clothing/head/cowboyhat/pink
 	name = "cowgirl hat"
 	icon_state = "cowboyhat_pink"
 	item_state = "cowboyhat_pink"
diff --git a/code/modules/clothing/shoes/miscellaneous.dm b/code/modules/clothing/shoes/miscellaneous.dm
index 9ad55d65e7a..923a8b4e5ab 100644
--- a/code/modules/clothing/shoes/miscellaneous.dm
+++ b/code/modules/clothing/shoes/miscellaneous.dm
@@ -235,23 +235,23 @@
 
 /obj/item/clothing/shoes/cowboyboots
 	name = "cowboy boots"
-	desc = "A pair a' brown boots."
+	desc = "A pair a' dark brown boots."
 	icon_state = "cowboyboots"
 	item_color = "cowboyboots"
 
-/obj/item/clothing/shoes/cowboyboots_black
+/obj/item/clothing/shoes/cowboyboots/black
 	name = "black cowboy boots"
 	desc = "A pair a' black rustlers' boots"
 	icon_state = "cowboyboots_black"
 	item_color = "cowboyboots_black"
 
-/obj/item/clothing/shoes/cowboyboots_white
+/obj/item/clothing/shoes/cowboyboots/white
 	name = "white cowboy boots"
 	desc = "For the rancher in us all."
 	icon_state = "cowboyboots_white"
 	item_color = "cowboyboots_white"
 
-/obj/item/clothing/shoes/cowboyboots_pink
+/obj/item/clothing/shoes/cowboyboots/pink
 	name = "pink cowgirl boots"
 	desc = "For a Rustlin' tustlin' cowgirl."
 	icon_state = "cowboyboots_pink"
diff --git a/icons/mob/head.dmi b/icons/mob/head.dmi
index f41205fb0fd..3f37086edb0 100644
Binary files a/icons/mob/head.dmi and b/icons/mob/head.dmi differ
diff --git a/icons/obj/clothing/hats.dmi b/icons/obj/clothing/hats.dmi
index abcd031c8ed..d1b9bb901fc 100644
Binary files a/icons/obj/clothing/hats.dmi and b/icons/obj/clothing/hats.dmi differ