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 54ea9f41857..886c6637c62 100644
--- a/code/datums/greyscale/config_types/greyscale_configs/greyscale_clothes.dm
+++ b/code/datums/greyscale/config_types/greyscale_configs/greyscale_clothes.dm
@@ -832,3 +832,12 @@
 /datum/greyscale_config/jester_hat/worn
 	name = "Jester Hat (Worn)"
 	icon_file = 'icons/mob/clothing/head/costume.dmi'
+
+/datum/greyscale_config/fedora
+	name = "Fedora"
+	icon_file = 'icons/obj/clothing/head/hats.dmi'
+	json_config = 'code/datums/greyscale/json_configs/fedora.json'
+
+/datum/greyscale_config/fedora/worn
+	name = "Fedora (Worn)"
+	icon_file = 'icons/mob/clothing/head/hats.dmi'
diff --git a/code/datums/greyscale/json_configs/fedora.json b/code/datums/greyscale/json_configs/fedora.json
new file mode 100644
index 00000000000..2b7f6d0f89f
--- /dev/null
+++ b/code/datums/greyscale/json_configs/fedora.json
@@ -0,0 +1,16 @@
+{
+	"fedora_greyscale": [
+		{
+			"type": "icon_state",
+			"icon_state": "fedora_base",
+			"blend_mode": "overlay",
+			"color_ids": [ 1 ]
+		},
+		{
+			"type": "icon_state",
+			"icon_state": "fedora_sash",
+			"blend_mode": "overlay",
+			"color_ids": [ 2 ]
+		}
+	]
+}
diff --git a/code/modules/clothing/head/fedora.dm b/code/modules/clothing/head/fedora.dm
index 51c5afa2eba..ff192c96f7a 100644
--- a/code/modules/clothing/head/fedora.dm
+++ b/code/modules/clothing/head/fedora.dm
@@ -1,10 +1,10 @@
 /obj/item/clothing/head/fedora
 	name = "fedora"
+	desc = "A really cool hat if you're a mobster. A really lame hat if you're not."
+	icon_state = "fedora"
 	icon = 'icons/obj/clothing/head/hats.dmi'
 	worn_icon = 'icons/mob/clothing/head/hats.dmi'
-	icon_state = "fedora"
-	inhand_icon_state = "fedora"
-	desc = "A really cool hat if you're a mobster. A really lame hat if you're not."
+	hair_mask = HAIR_MASK_HIDE_ABOVE_45_DEG_LOW
 
 /obj/item/clothing/head/fedora/Initialize(mapload)
 	. = ..()
@@ -45,3 +45,11 @@
 	desc = "A beige fedora with a piece of paper saying \"PRESS\" stuck in its rim."
 	icon_state = "fedora_press"
 	inhand_icon_state = null
+
+/obj/item/clothing/head/fedora/greyscale
+	icon_state = "fedora_greyscale"
+	inhand_icon_state = null
+	greyscale_colors = "#F0DAB4#794D2E"
+	greyscale_config = /datum/greyscale_config/fedora
+	greyscale_config_worn = /datum/greyscale_config/fedora/worn
+	flags_1 = IS_PLAYER_COLORABLE_1
diff --git a/code/modules/clothing/head/jobs.dm b/code/modules/clothing/head/jobs.dm
index a0d7dafcfd7..0e78e4859bd 100644
--- a/code/modules/clothing/head/jobs.dm
+++ b/code/modules/clothing/head/jobs.dm
@@ -175,7 +175,6 @@
 	desc = "There's only one man who can sniff out the dirty stench of crime, and he's likely wearing this hat."
 	armor_type = /datum/armor/fedora_det_hat
 	icon_state = "detective"
-	inhand_icon_state = "det_hat"
 	interaction_flags_click = NEED_DEXTERITY|NEED_HANDS|ALLOW_RESTING
 	dog_fashion = /datum/dog_fashion/head/detective
 	/// Path for the flask that spawns inside their hat roundstart
@@ -242,7 +241,6 @@
 	desc = "There's only one man can try to stop an evil villain."
 	armor_type = /datum/armor/fedora_det_hat
 	icon_state = "detective"
-	inhand_icon_state = "det_hat"
 	dog_fashion = /datum/dog_fashion/head/detective
 	interaction_flags_click = FORBID_TELEKINESIS_REACH|ALLOW_RESTING
 	///prefix our phrases must begin with
diff --git a/code/modules/unit_tests/screenshots/screenshot_antag_icons_spy.png b/code/modules/unit_tests/screenshots/screenshot_antag_icons_spy.png
index 103e9d60faf..fbfbae1aeec 100644
Binary files a/code/modules/unit_tests/screenshots/screenshot_antag_icons_spy.png and b/code/modules/unit_tests/screenshots/screenshot_antag_icons_spy.png differ
diff --git a/code/modules/vending/clothesmate.dm b/code/modules/vending/clothesmate.dm
index 738ba83e158..df34918a5dc 100644
--- a/code/modules/vending/clothesmate.dm
+++ b/code/modules/vending/clothesmate.dm
@@ -32,6 +32,9 @@
 				/obj/item/clothing/head/chaplain/taqiyah/red = 3,
 				/obj/item/clothing/head/hats/tophat = 3,
 				/obj/item/clothing/head/fedora = 3,
+				/obj/item/clothing/head/fedora/white = 3,
+				/obj/item/clothing/head/fedora/beige = 3,
+				/obj/item/clothing/head/fedora/greyscale = 3,
 				/obj/item/clothing/head/hats/bowler = 3,
 				/obj/item/clothing/head/cowboy/white = 3,
 				/obj/item/clothing/head/cowboy/grey = 3,
diff --git a/icons/mob/clothing/head/hats.dmi b/icons/mob/clothing/head/hats.dmi
index 1ff429b68b1..7d603fed0fa 100644
Binary files a/icons/mob/clothing/head/hats.dmi and b/icons/mob/clothing/head/hats.dmi differ
diff --git a/icons/mob/clothing/suits/jacket.dmi b/icons/mob/clothing/suits/jacket.dmi
index 869966528b2..3cd0f0c464b 100644
Binary files a/icons/mob/clothing/suits/jacket.dmi and b/icons/mob/clothing/suits/jacket.dmi differ
diff --git a/icons/mob/clothing/under/suits.dmi b/icons/mob/clothing/under/suits.dmi
index e8fd6a820d3..b858489717d 100644
Binary files a/icons/mob/clothing/under/suits.dmi and b/icons/mob/clothing/under/suits.dmi differ
diff --git a/icons/mob/human/hair_masks.dmi b/icons/mob/human/hair_masks.dmi
index bb7b55e0cc3..dd54ce1e886 100644
Binary files a/icons/mob/human/hair_masks.dmi and b/icons/mob/human/hair_masks.dmi differ
diff --git a/icons/mob/inhands/clothing/hats_lefthand.dmi b/icons/mob/inhands/clothing/hats_lefthand.dmi
index 6ad1f8886c9..3ea3bd8ae5b 100644
Binary files a/icons/mob/inhands/clothing/hats_lefthand.dmi and b/icons/mob/inhands/clothing/hats_lefthand.dmi differ
diff --git a/icons/mob/inhands/clothing/hats_righthand.dmi b/icons/mob/inhands/clothing/hats_righthand.dmi
index 3aba15568ef..f0d5f3fa3e2 100644
Binary files a/icons/mob/inhands/clothing/hats_righthand.dmi and b/icons/mob/inhands/clothing/hats_righthand.dmi differ
diff --git a/icons/obj/clothing/head/hats.dmi b/icons/obj/clothing/head/hats.dmi
index 2ce0eebb2ad..70872619f9b 100644
Binary files a/icons/obj/clothing/head/hats.dmi and b/icons/obj/clothing/head/hats.dmi differ
diff --git a/icons/obj/clothing/suits/jacket.dmi b/icons/obj/clothing/suits/jacket.dmi
index b867e7da3a7..53d035518e7 100644
Binary files a/icons/obj/clothing/suits/jacket.dmi and b/icons/obj/clothing/suits/jacket.dmi differ
diff --git a/icons/obj/clothing/under/suits.dmi b/icons/obj/clothing/under/suits.dmi
index 42c79981df6..22699ebf0c6 100644
Binary files a/icons/obj/clothing/under/suits.dmi and b/icons/obj/clothing/under/suits.dmi differ