diff --git a/code/game/machinery/vendors/wardrobe_vendors.dm b/code/game/machinery/vendors/wardrobe_vendors.dm
index 61c2e51e4da..e8bac692664 100644
--- a/code/game/machinery/vendors/wardrobe_vendors.dm
+++ b/code/game/machinery/vendors/wardrobe_vendors.dm
@@ -23,6 +23,7 @@
 					/obj/item/clothing/under/rank/security/officer/fancy = 4,
 					/obj/item/clothing/under/rank/security/officer/skirt/fancy = 4,
 					/obj/item/clothing/head/soft/sec/corp = 4,
+					/obj/item/clothing/head/cowboyhat/sec = 4,
 					/obj/item/clothing/head/officer = 4,
 					/obj/item/clothing/head/beret/sec = 4,
 					/obj/item/clothing/head/soft/sec = 4,
@@ -62,6 +63,7 @@
 				/obj/item/clothing/head/officer = 40,
 				/obj/item/clothing/head/beret/sec = 40,
 				/obj/item/clothing/head/soft/sec = 40,
+				/obj/item/clothing/head/cowboyhat/sec = 50,
 				/obj/item/clothing/head/drillsgt = 40,
 				/obj/item/clothing/mask/bandana/red = 40,
 				/obj/item/clothing/mask/balaclava = 60,
diff --git a/code/modules/client/preference/loadout/loadout_hat.dm b/code/modules/client/preference/loadout/loadout_hat.dm
index c67f34595a5..5589f7f2522 100644
--- a/code/modules/client/preference/loadout/loadout_hat.dm
+++ b/code/modules/client/preference/loadout/loadout_hat.dm
@@ -148,6 +148,11 @@
 	display_name = "Cowboy hat, pink"
 	path = /obj/item/clothing/head/cowboyhat/pink
 
+/datum/gear/hat/cowboyhat/sec
+	display_name = "Cowboy hat, security"
+	path = /obj/item/clothing/head/cowboyhat/sec
+	allowed_roles = list("Head of Security", "Warden", "Security Officer")
+
 /datum/gear/hat/beret_purple
 	display_name = "Beret, purple"
 	path = /obj/item/clothing/head/beret/purple_normal
diff --git a/code/modules/clothing/head/misc_hats.dm b/code/modules/clothing/head/misc_hats.dm
index 02e7d94c90e..1e4577a7cd7 100644
--- a/code/modules/clothing/head/misc_hats.dm
+++ b/code/modules/clothing/head/misc_hats.dm
@@ -247,6 +247,12 @@
 	item_state = "cowboyhat"
 	desc = "For the Rancher in us all."
 
+	sprite_sheets = list(
+		"Vox" = 'icons/mob/clothing/species/vox/head.dmi',
+		"Drask" = 'icons/mob/clothing/species/drask/head.dmi',
+		"Grey" = 'icons/mob/clothing/species/grey/head.dmi'
+		)
+
 /obj/item/clothing/head/cowboyhat/tan
 	name = "tan cowboy hat"
 	icon_state = "cowboyhat_tan"
@@ -271,6 +277,12 @@
 	item_state = "cowboyhat_pink"
 	desc = "For those buckle bunnies wanta' become a real buckaroo."
 
+/obj/item/clothing/head/cowboyhat/sec
+	name = "security cowboy hat"
+	desc = "Secway is your horse."
+	icon_state = "cowboyhat_sec"
+	item_state = "cowboyhat_sec"
+
 /obj/item/clothing/head/fedora
 	name = "fedora"
 	desc = "A great hat ruined by being within fifty yards of you."
diff --git a/icons/mob/clothing/head.dmi b/icons/mob/clothing/head.dmi
index bd4029c619f..e7831943479 100644
Binary files a/icons/mob/clothing/head.dmi and b/icons/mob/clothing/head.dmi differ
diff --git a/icons/mob/clothing/species/drask/head.dmi b/icons/mob/clothing/species/drask/head.dmi
index 4304dbd35b9..4bf588269a3 100644
Binary files a/icons/mob/clothing/species/drask/head.dmi and b/icons/mob/clothing/species/drask/head.dmi differ
diff --git a/icons/mob/clothing/species/grey/head.dmi b/icons/mob/clothing/species/grey/head.dmi
index 72c0c290982..dc37f60988d 100644
Binary files a/icons/mob/clothing/species/grey/head.dmi and b/icons/mob/clothing/species/grey/head.dmi differ
diff --git a/icons/mob/clothing/species/vox/head.dmi b/icons/mob/clothing/species/vox/head.dmi
index 5acee49cd61..cbf99e636e7 100644
Binary files a/icons/mob/clothing/species/vox/head.dmi and b/icons/mob/clothing/species/vox/head.dmi differ
diff --git a/icons/obj/clothing/hats.dmi b/icons/obj/clothing/hats.dmi
index 9cef001574b..4f327db6928 100644
Binary files a/icons/obj/clothing/hats.dmi and b/icons/obj/clothing/hats.dmi differ
diff --git a/tools/loadout_converter/loadout_converter.json b/tools/loadout_converter/loadout_converter.json
index 055841f3c71..54cf28b2975 100644
--- a/tools/loadout_converter/loadout_converter.json
+++ b/tools/loadout_converter/loadout_converter.json
@@ -174,6 +174,7 @@
 		"cowboy+hat%2c+white": "/datum/gear/hat/cowboyhat/white",
 		"cowboy+hat%2c+pink": "/datum/gear/hat/cowboyhat/pink",
 		"cowboy+hat%2c+brown": "/datum/gear/hat/cowboyhat",
+		"cowboy+hat%2c+sec": "/datum/gear/hat/cowboyhat/sec",
 		"cowboy+hat": "/datum/gear/hat/cowboyhat",
 		"beret%2c+purple": "/datum/gear/hat/beret_purple",
 		"beret%2c+black": "/datum/gear/hat/beret_black",