diff --git a/code/datums/greyscale/config_types/greyscale_configs/greyscale_clothes.dm b/code/datums/greyscale/config_types/greyscale_configs/greyscale_clothes.dm
index ea4233623a2..377a2fa1693 100644
--- a/code/datums/greyscale/config_types/greyscale_configs/greyscale_clothes.dm
+++ b/code/datums/greyscale/config_types/greyscale_configs/greyscale_clothes.dm
@@ -797,3 +797,30 @@
 /datum/greyscale_config/gi/worn
 	name = "Gi (Worn)"
 	icon_file = 'icons/mob/clothing/under/costume.dmi'
+
+/datum/greyscale_config/jester_suit
+	name = "Jester Suit"
+	icon_file = 'icons/obj/clothing/under/civilian.dmi'
+	json_config = 'code/datums/greyscale/json_configs/jester_suit.json'
+
+/datum/greyscale_config/jester_suit/worn
+	name = "Jester Suit (Worn)"
+	icon_file = 'icons/mob/clothing/under/civilian.dmi'
+
+/datum/greyscale_config/jester_shoes
+	name = "Jester Shoes"
+	icon_file = 'icons/obj/clothing/shoes.dmi'
+	json_config = 'code/datums/greyscale/json_configs/jester_shoes.json'
+
+/datum/greyscale_config/jester_shoes/worn
+	name = "Jester Shoes (Worn)"
+	icon_file = 'icons/mob/clothing/feet.dmi'
+
+/datum/greyscale_config/jester_hat
+	name = "Jester Hat"
+	icon_file = 'icons/obj/clothing/head/costume.dmi'
+	json_config = 'code/datums/greyscale/json_configs/jester_hat.json'
+
+/datum/greyscale_config/jester_hat/worn
+	name = "Jester Hat (Worn)"
+	icon_file = 'icons/mob/clothing/head/costume.dmi'
diff --git a/code/datums/greyscale/json_configs/jester_hat.json b/code/datums/greyscale/json_configs/jester_hat.json
new file mode 100644
index 00000000000..b5147e7a009
--- /dev/null
+++ b/code/datums/greyscale/json_configs/jester_hat.json
@@ -0,0 +1,21 @@
+{
+	"jester_map": [
+		{
+			"type": "icon_state",
+			"icon_state": "jester_a",
+			"blend_mode": "overlay",
+			"color_ids": [ 1 ]
+		},
+		{
+			"type": "icon_state",
+			"icon_state": "jester_b",
+			"blend_mode": "overlay",
+			"color_ids": [ 2 ]
+		},
+		{
+			"type": "icon_state",
+			"icon_state": "jester_bells",
+			"blend_mode": "overlay"
+		}
+	]
+}
diff --git a/code/datums/greyscale/json_configs/jester_shoes.json b/code/datums/greyscale/json_configs/jester_shoes.json
new file mode 100644
index 00000000000..b5147e7a009
--- /dev/null
+++ b/code/datums/greyscale/json_configs/jester_shoes.json
@@ -0,0 +1,21 @@
+{
+	"jester_map": [
+		{
+			"type": "icon_state",
+			"icon_state": "jester_a",
+			"blend_mode": "overlay",
+			"color_ids": [ 1 ]
+		},
+		{
+			"type": "icon_state",
+			"icon_state": "jester_b",
+			"blend_mode": "overlay",
+			"color_ids": [ 2 ]
+		},
+		{
+			"type": "icon_state",
+			"icon_state": "jester_bells",
+			"blend_mode": "overlay"
+		}
+	]
+}
diff --git a/code/datums/greyscale/json_configs/jester_suit.json b/code/datums/greyscale/json_configs/jester_suit.json
new file mode 100644
index 00000000000..aac60f18be7
--- /dev/null
+++ b/code/datums/greyscale/json_configs/jester_suit.json
@@ -0,0 +1,16 @@
+{
+	"jester_map": [
+		{
+			"type": "icon_state",
+			"icon_state": "jester_a",
+			"blend_mode": "overlay",
+			"color_ids": [ 1 ]
+		},
+		{
+			"type": "icon_state",
+			"icon_state": "jester_b",
+			"blend_mode": "overlay",
+			"color_ids": [ 2 ]
+		}
+	]
+}
diff --git a/code/modules/clothing/head/hat.dm b/code/modules/clothing/head/hat.dm
index 846f49ad957..6fbc2232b1b 100644
--- a/code/modules/clothing/head/hat.dm
+++ b/code/modules/clothing/head/hat.dm
@@ -192,9 +192,15 @@
 /obj/item/clothing/head/costume/jester
 	name = "jester hat"
 	desc = "A hat with bells, to add some merriness to the suit."
-	icon_state = "jester_hat"
+	icon_state = "jester_map"
+	greyscale_colors = "#00ff00#ff0000"
+	greyscale_config = /datum/greyscale_config/jester_hat
+	greyscale_config_worn = /datum/greyscale_config/jester_hat/worn
+	flags_1 = IS_PLAYER_COLORABLE_1
 
-/obj/item/clothing/head/costume/jester/alt
+/obj/item/clothing/head/costume/jesteralt
+	name = "jester hat"
+	desc = "A hat with bells, to add some merriness to the suit."
 	icon_state = "jester2"
 
 /obj/item/clothing/head/costume/rice_hat
diff --git a/code/modules/clothing/shoes/costume.dm b/code/modules/clothing/shoes/costume.dm
index 1e15f25e1f6..bf8000d9a08 100644
--- a/code/modules/clothing/shoes/costume.dm
+++ b/code/modules/clothing/shoes/costume.dm
@@ -105,8 +105,12 @@
 /obj/item/clothing/shoes/jester_shoes
 	name = "jester shoes"
 	desc = "Shoes that jingle with every step!!"
-	icon_state = "green_jester_shoes"
+	icon_state = "jester_map"
 	inhand_icon_state = null
+	greyscale_colors = "#00ff00#ff0000"
+	greyscale_config = /datum/greyscale_config/jester_shoes
+	greyscale_config_worn = /datum/greyscale_config/jester_shoes/worn
+	flags_1 = IS_PLAYER_COLORABLE_1
 
 /obj/item/clothing/shoes/jester_shoes/Initialize(mapload)
 	. = ..()
diff --git a/code/modules/clothing/under/jobs/civilian/clown_mime.dm b/code/modules/clothing/under/jobs/civilian/clown_mime.dm
index cb5a89990b0..98571182f29 100644
--- a/code/modules/clothing/under/jobs/civilian/clown_mime.dm
+++ b/code/modules/clothing/under/jobs/civilian/clown_mime.dm
@@ -76,9 +76,15 @@
 /obj/item/clothing/under/rank/civilian/clown/jester
 	name = "jester suit"
 	desc = "A jolly dress, well suited to entertain your master, nuncle."
-	icon_state = "jester"
+	icon_state = "jester_map"
+	greyscale_colors = "#00ff00#ff0000"
+	greyscale_config = /datum/greyscale_config/jester_suit
+	greyscale_config_worn = /datum/greyscale_config/jester_suit/worn
+	flags_1 = IS_PLAYER_COLORABLE_1
 
-/obj/item/clothing/under/rank/civilian/clown/jester/alt
+/obj/item/clothing/under/rank/civilian/clown/jesteralt
+	name = "jester suit"
+	desc = "A jolly dress, well suited to entertain your master, nuncle."
 	icon_state = "jester2"
 
 /obj/item/clothing/under/rank/civilian/clown/sexy
diff --git a/icons/mob/clothing/feet.dmi b/icons/mob/clothing/feet.dmi
index 612d82302e7..3ae1eb68e86 100644
Binary files a/icons/mob/clothing/feet.dmi and b/icons/mob/clothing/feet.dmi differ
diff --git a/icons/mob/clothing/head/costume.dmi b/icons/mob/clothing/head/costume.dmi
index 4bce495a291..1f4f12ff8c8 100644
Binary files a/icons/mob/clothing/head/costume.dmi and b/icons/mob/clothing/head/costume.dmi differ
diff --git a/icons/mob/clothing/under/civilian.dmi b/icons/mob/clothing/under/civilian.dmi
index 7283996c3b1..d172185d4a4 100644
Binary files a/icons/mob/clothing/under/civilian.dmi and b/icons/mob/clothing/under/civilian.dmi differ
diff --git a/icons/obj/clothing/head/costume.dmi b/icons/obj/clothing/head/costume.dmi
index e72c278b6eb..25bc62a5314 100644
Binary files a/icons/obj/clothing/head/costume.dmi and b/icons/obj/clothing/head/costume.dmi differ
diff --git a/icons/obj/clothing/shoes.dmi b/icons/obj/clothing/shoes.dmi
index 37f561bb44b..ec2a128a865 100644
Binary files a/icons/obj/clothing/shoes.dmi and b/icons/obj/clothing/shoes.dmi differ
diff --git a/icons/obj/clothing/under/civilian.dmi b/icons/obj/clothing/under/civilian.dmi
index 8552c5b9660..8f7c28ca047 100644
Binary files a/icons/obj/clothing/under/civilian.dmi and b/icons/obj/clothing/under/civilian.dmi differ
diff --git a/tools/UpdatePaths/Scripts/82339_jester_repath.txt b/tools/UpdatePaths/Scripts/82339_jester_repath.txt
new file mode 100644
index 00000000000..1c7012ebf58
--- /dev/null
+++ b/tools/UpdatePaths/Scripts/82339_jester_repath.txt
@@ -0,0 +1,2 @@
+/obj/item/clothing/head/costume/jester/alt : /obj/item/clothing/head/costume/jesteralt {@OLD}
+/obj/item/clothing/under/rank/civilian/clown/jester/alt : /obj/item/clothing/under/rank/civilian/clown/jesteralt {@OLD}