diff --git a/editor/plugins/tile_map_editor_plugin.cpp b/editor/plugins/tile_map_editor_plugin.cpp
index ed1fa9b217..b5e2a8675f 100644
--- a/editor/plugins/tile_map_editor_plugin.cpp
+++ b/editor/plugins/tile_map_editor_plugin.cpp
@@ -31,6 +31,7 @@
 #include "tile_map_editor_plugin.h"
 
 #include "canvas_item_editor_plugin.h"
+#include "core/math/math_funcs.h"
 #include "core/os/input.h"
 #include "core/os/keyboard.h"
 #include "editor/editor_scale.h"
@@ -65,13 +66,11 @@ void TileMapEditor::_notification(int p_what) {
 
 		case NOTIFICATION_ENTER_TREE: {
 
-			transp->set_icon(get_icon("Transpose", "EditorIcons"));
-			mirror_x->set_icon(get_icon("MirrorX", "EditorIcons"));
-			mirror_y->set_icon(get_icon("MirrorY", "EditorIcons"));
-			rotate_0->set_icon(get_icon("Rotate0", "EditorIcons"));
-			rotate_90->set_icon(get_icon("Rotate90", "EditorIcons"));
-			rotate_180->set_icon(get_icon("Rotate180", "EditorIcons"));
-			rotate_270->set_icon(get_icon("Rotate270", "EditorIcons"));
+			rotate_left_button->set_icon(get_icon("Rotate270", "EditorIcons"));
+			rotate_right_button->set_icon(get_icon("Rotate90", "EditorIcons"));
+			flip_horizontal_button->set_icon(get_icon("MirrorX", "EditorIcons"));
+			flip_vertical_button->set_icon(get_icon("MirrorY", "EditorIcons"));
+			clear_transform_button->set_icon(get_icon("Clear", "EditorIcons"));
 
 			search_box->set_right_icon(get_icon("Search", "EditorIcons"));
 			search_box->set_clear_button_enabled(true);
@@ -357,6 +356,10 @@ void TileMapEditor::_update_palette() {
 	if (!node)
 		return;
 
+	// Update the clear button
+	clear_transform_button->set_disabled(!flip_h && !flip_v && !transpose);
+
+	// Update the palette
 	Vector<int> selected = get_selected_tiles();
 	palette->clear();
 	manual_palette->clear();
@@ -429,9 +432,6 @@ void TileMapEditor::_update_palette() {
 		Ref<Texture> tex = tileset->tile_get_texture(entries[i].id);
 
 		if (tex.is_valid()) {
-			Color color = tileset->tile_get_modulate(entries[i].id);
-			palette->set_item_icon_modulate(palette->get_item_count() - 1, color);
-
 			Rect2 region = tileset->tile_get_region(entries[i].id);
 
 			if (tileset->tile_get_tile_mode(entries[i].id) == TileSet::AUTO_TILE || tileset->tile_get_tile_mode(entries[i].id) == TileSet::ATLAS_TILE) {
@@ -440,10 +440,25 @@ void TileMapEditor::_update_palette() {
 				region.position += (region.size + Vector2(spacing, spacing)) * tileset->autotile_get_icon_coordinate(entries[i].id);
 			}
 
-			if (!region.has_no_area())
+			// Transpose and flip
+			palette->set_item_icon_transposed(palette->get_item_count() - 1, transpose);
+			if (flip_h) {
+				region.size.x = -region.size.x;
+			}
+			if (flip_v) {
+				region.size.y = -region.size.y;
+			}
+
+			// Set region
+			if (region.size != Size2())
 				palette->set_item_icon_region(palette->get_item_count() - 1, region);
 
+			// Set icon
 			palette->set_item_icon(palette->get_item_count() - 1, tex);
+
+			// Modulation
+			Color color = tileset->tile_get_modulate(entries[i].id);
+			palette->set_item_icon_modulate(palette->get_item_count() - 1, color);
 		}
 
 		palette->set_item_metadata(palette->get_item_count() - 1, entries[i].id);
@@ -519,11 +534,11 @@ void TileMapEditor::_pick_tile(const Point2 &p_pos) {
 	selected.push_back(id);
 	set_selected_tiles(selected);
 
-	mirror_x->set_pressed(node->is_cell_x_flipped(p_pos.x, p_pos.y));
-	mirror_y->set_pressed(node->is_cell_y_flipped(p_pos.x, p_pos.y));
-	transp->set_pressed(node->is_cell_transposed(p_pos.x, p_pos.y));
+	flip_h = node->is_cell_x_flipped(p_pos.x, p_pos.y);
+	flip_v = node->is_cell_y_flipped(p_pos.x, p_pos.y);
+	transpose = node->is_cell_transposed(p_pos.x, p_pos.y);
 
-	_update_transform_buttons();
+	_update_palette();
 	CanvasItemEditor::get_singleton()->update_viewport();
 }
 
@@ -1366,22 +1381,19 @@ bool TileMapEditor::forward_gui_input(const Ref<InputEvent> &p_event) {
 		}
 		if (ED_IS_SHORTCUT("tile_map_editor/mirror_x", p_event)) {
 			flip_h = !flip_h;
-			mirror_x->set_pressed(flip_h);
-			_update_transform_buttons();
+			_update_palette();
 			CanvasItemEditor::get_singleton()->update_viewport();
 			return true;
 		}
 		if (ED_IS_SHORTCUT("tile_map_editor/mirror_y", p_event)) {
 			flip_v = !flip_v;
-			mirror_y->set_pressed(flip_v);
-			_update_transform_buttons();
+			_update_palette();
 			CanvasItemEditor::get_singleton()->update_viewport();
 			return true;
 		}
 		if (ED_IS_SHORTCUT("tile_map_editor/transpose", p_event)) {
 			transpose = !transpose;
-			transp->set_pressed(transpose);
-			_update_transform_buttons();
+			_update_palette();
 			CanvasItemEditor::get_singleton()->update_viewport();
 			return true;
 		}
@@ -1664,7 +1676,10 @@ void TileMapEditor::_bind_methods() {
 	ClassDB::bind_method(D_METHOD("_canvas_mouse_enter"), &TileMapEditor::_canvas_mouse_enter);
 	ClassDB::bind_method(D_METHOD("_canvas_mouse_exit"), &TileMapEditor::_canvas_mouse_exit);
 	ClassDB::bind_method(D_METHOD("_tileset_settings_changed"), &TileMapEditor::_tileset_settings_changed);
-	ClassDB::bind_method(D_METHOD("_update_transform_buttons"), &TileMapEditor::_update_transform_buttons);
+	ClassDB::bind_method(D_METHOD("_rotate"), &TileMapEditor::_rotate);
+	ClassDB::bind_method(D_METHOD("_flip_horizontal"), &TileMapEditor::_flip_horizontal);
+	ClassDB::bind_method(D_METHOD("_flip_vertical"), &TileMapEditor::_flip_vertical);
+	ClassDB::bind_method(D_METHOD("_clear_transform"), &TileMapEditor::_clear_transform);
 	ClassDB::bind_method(D_METHOD("_palette_selected"), &TileMapEditor::_palette_selected);
 	ClassDB::bind_method(D_METHOD("_palette_multi_selected"), &TileMapEditor::_palette_multi_selected);
 
@@ -1689,37 +1704,66 @@ TileMapEditor::CellOp TileMapEditor::_get_op_from_cell(const Point2i &p_pos) {
 	return op;
 }
 
-void TileMapEditor::_update_transform_buttons(Object *p_button) {
-	//ERR_FAIL_NULL(p_button);
-	ToolButton *b = Object::cast_to<ToolButton>(p_button);
-	//ERR_FAIL_COND(!b);
+void TileMapEditor::_rotate(int steps) {
+	const bool normal_rotation_matrix[][3] = {
+		{ false, false, false },
+		{ true, true, false },
+		{ false, true, true },
+		{ true, false, true }
+	};
 
-	if (b == rotate_0) {
-		mirror_x->set_pressed(false);
-		mirror_y->set_pressed(false);
-		transp->set_pressed(false);
-	} else if (b == rotate_90) {
-		mirror_x->set_pressed(true);
-		mirror_y->set_pressed(false);
-		transp->set_pressed(true);
-	} else if (b == rotate_180) {
-		mirror_x->set_pressed(true);
-		mirror_y->set_pressed(true);
-		transp->set_pressed(false);
-	} else if (b == rotate_270) {
-		mirror_x->set_pressed(false);
-		mirror_y->set_pressed(true);
-		transp->set_pressed(true);
+	const bool mirrored_rotation_matrix[][3] = {
+		{ false, true, false },
+		{ true, true, true },
+		{ false, false, true },
+		{ true, false, false }
+	};
+
+	if (transpose ^ flip_h ^ flip_v) {
+		// Odd number of flags activated = mirrored rotation
+		for (int i = 0; i < 4; i++) {
+			if (transpose == mirrored_rotation_matrix[i][0] &&
+					flip_h == mirrored_rotation_matrix[i][1] &&
+					flip_v == mirrored_rotation_matrix[i][2]) {
+				int new_id = Math::wrapi(i + steps, 0, 4);
+				transpose = mirrored_rotation_matrix[new_id][0];
+				flip_h = mirrored_rotation_matrix[new_id][1];
+				flip_v = mirrored_rotation_matrix[new_id][2];
+			}
+		}
+	} else {
+		// Even number of flags activated = normal rotation
+		for (int i = 0; i < 4; i++) {
+			if (transpose == normal_rotation_matrix[i][0] &&
+					flip_h == normal_rotation_matrix[i][1] &&
+					flip_v == normal_rotation_matrix[i][2]) {
+				int new_id = Math::wrapi(i + steps, 0, 4);
+				transpose = normal_rotation_matrix[new_id][0];
+				flip_h = normal_rotation_matrix[new_id][1];
+				flip_v = normal_rotation_matrix[new_id][2];
+				break;
+			}
+		}
 	}
 
-	flip_h = mirror_x->is_pressed();
-	flip_v = mirror_y->is_pressed();
-	transpose = transp->is_pressed();
+	_update_palette();
+}
 
-	rotate_0->set_pressed(!flip_h && !flip_v && !transpose);
-	rotate_90->set_pressed(flip_h && !flip_v && transpose);
-	rotate_180->set_pressed(flip_h && flip_v && !transpose);
-	rotate_270->set_pressed(!flip_h && flip_v && transpose);
+void TileMapEditor::_flip_horizontal() {
+	flip_h = !flip_h;
+	_update_palette();
+}
+
+void TileMapEditor::_flip_vertical() {
+	flip_v = !flip_v;
+	_update_palette();
+}
+
+void TileMapEditor::_clear_transform() {
+	transpose = false;
+	flip_h = false;
+	flip_v = false;
+	_update_palette();
 }
 
 TileMapEditor::TileMapEditor(EditorNode *p_editor) {
@@ -1752,10 +1796,8 @@ TileMapEditor::TileMapEditor(EditorNode *p_editor) {
 	ED_SHORTCUT("tile_map_editor/mirror_x", TTR("Mirror X"), KEY_A);
 	ED_SHORTCUT("tile_map_editor/mirror_y", TTR("Mirror Y"), KEY_S);
 
-	HBoxContainer *tool_hb1 = memnew(HBoxContainer);
-	add_child(tool_hb1);
-	HBoxContainer *tool_hb2 = memnew(HBoxContainer);
-	add_child(tool_hb2);
+	HBoxContainer *tool_hb = memnew(HBoxContainer);
+	add_child(tool_hb);
 
 	manual_button = memnew(CheckBox);
 	manual_button->set_text("Disable Autotile");
@@ -1840,52 +1882,37 @@ TileMapEditor::TileMapEditor(EditorNode *p_editor) {
 	p->connect("id_pressed", this, "_menu_option");
 
 	toolbar->add_child(options);
+	rotate_left_button = memnew(ToolButton);
+	rotate_left_button->set_tooltip(TTR("Rotate left"));
+	rotate_left_button->set_focus_mode(FOCUS_NONE);
+	rotate_left_button->connect("pressed", this, "_rotate", varray(-1));
+	tool_hb->add_child(rotate_left_button);
 
-	transp = memnew(ToolButton);
-	transp->set_toggle_mode(true);
-	transp->set_tooltip(TTR("Transpose") + " (" + ED_GET_SHORTCUT("tile_map_editor/transpose")->get_as_text() + ")");
-	transp->set_focus_mode(FOCUS_NONE);
-	transp->connect("pressed", this, "_update_transform_buttons", make_binds(transp));
-	tool_hb1->add_child(transp);
-	mirror_x = memnew(ToolButton);
-	mirror_x->set_toggle_mode(true);
-	mirror_x->set_tooltip(TTR("Mirror X") + " (" + ED_GET_SHORTCUT("tile_map_editor/mirror_x")->get_as_text() + ")");
-	mirror_x->set_focus_mode(FOCUS_NONE);
-	mirror_x->connect("pressed", this, "_update_transform_buttons", make_binds(mirror_x));
-	tool_hb1->add_child(mirror_x);
-	mirror_y = memnew(ToolButton);
-	mirror_y->set_toggle_mode(true);
-	mirror_y->set_tooltip(TTR("Mirror Y") + " (" + ED_GET_SHORTCUT("tile_map_editor/mirror_y")->get_as_text() + ")");
-	mirror_y->set_focus_mode(FOCUS_NONE);
-	mirror_y->connect("pressed", this, "_update_transform_buttons", make_binds(mirror_y));
-	tool_hb1->add_child(mirror_y);
+	rotate_right_button = memnew(ToolButton);
+	rotate_right_button->set_tooltip(TTR("Rotate right"));
+	rotate_right_button->set_focus_mode(FOCUS_NONE);
+	rotate_right_button->connect("pressed", this, "_rotate", varray(1));
+	tool_hb->add_child(rotate_right_button);
 
-	rotate_0 = memnew(ToolButton);
-	rotate_0->set_toggle_mode(true);
-	rotate_0->set_tooltip(TTR("Rotate 0 degrees"));
-	rotate_0->set_focus_mode(FOCUS_NONE);
-	rotate_0->connect("pressed", this, "_update_transform_buttons", make_binds(rotate_0));
-	tool_hb2->add_child(rotate_0);
-	rotate_90 = memnew(ToolButton);
-	rotate_90->set_toggle_mode(true);
-	rotate_90->set_tooltip(TTR("Rotate 90 degrees"));
-	rotate_90->set_focus_mode(FOCUS_NONE);
-	rotate_90->connect("pressed", this, "_update_transform_buttons", make_binds(rotate_90));
-	tool_hb2->add_child(rotate_90);
-	rotate_180 = memnew(ToolButton);
-	rotate_180->set_toggle_mode(true);
-	rotate_180->set_tooltip(TTR("Rotate 180 degrees"));
-	rotate_180->set_focus_mode(FOCUS_NONE);
-	rotate_180->connect("pressed", this, "_update_transform_buttons", make_binds(rotate_180));
-	tool_hb2->add_child(rotate_180);
-	rotate_270 = memnew(ToolButton);
-	rotate_270->set_toggle_mode(true);
-	rotate_270->set_tooltip(TTR("Rotate 270 degrees"));
-	rotate_270->set_focus_mode(FOCUS_NONE);
-	rotate_270->connect("pressed", this, "_update_transform_buttons", make_binds(rotate_270));
-	tool_hb2->add_child(rotate_270);
+	flip_horizontal_button = memnew(ToolButton);
+	flip_horizontal_button->set_tooltip(TTR("Flip horizontally"));
+	flip_horizontal_button->set_focus_mode(FOCUS_NONE);
+	flip_horizontal_button->connect("pressed", this, "_flip_horizontal");
+	tool_hb->add_child(flip_horizontal_button);
 
-	rotate_0->set_pressed(true);
+	flip_vertical_button = memnew(ToolButton);
+	flip_vertical_button->set_tooltip(TTR("Flip vertically"));
+	flip_vertical_button->set_focus_mode(FOCUS_NONE);
+	flip_vertical_button->connect("pressed", this, "_flip_vertical");
+	tool_hb->add_child(flip_vertical_button);
+
+	clear_transform_button = memnew(ToolButton);
+	clear_transform_button->set_tooltip(TTR("Clear transform"));
+	clear_transform_button->set_focus_mode(FOCUS_NONE);
+	clear_transform_button->connect("pressed", this, "_clear_transform");
+	tool_hb->add_child(clear_transform_button);
+
+	clear_transform_button->set_disabled(true);
 }
 
 TileMapEditor::~TileMapEditor() {
diff --git a/editor/plugins/tile_map_editor_plugin.h b/editor/plugins/tile_map_editor_plugin.h
index 3d44647a1b..68e5806ee5 100644
--- a/editor/plugins/tile_map_editor_plugin.h
+++ b/editor/plugins/tile_map_editor_plugin.h
@@ -93,13 +93,13 @@ class TileMapEditor : public VBoxContainer {
 
 	Label *tile_info;
 	MenuButton *options;
-	ToolButton *transp;
-	ToolButton *mirror_x;
-	ToolButton *mirror_y;
-	ToolButton *rotate_0;
-	ToolButton *rotate_90;
-	ToolButton *rotate_180;
-	ToolButton *rotate_270;
+
+	ToolButton *flip_horizontal_button;
+	ToolButton *flip_vertical_button;
+	ToolButton *rotate_left_button;
+	ToolButton *rotate_right_button;
+	ToolButton *clear_transform_button;
+
 	CheckBox *manual_button;
 
 	Tool tool;
@@ -196,11 +196,15 @@ class TileMapEditor : public VBoxContainer {
 	void _tileset_settings_changed();
 	void _icon_size_changed(float p_value);
 
+	void _clear_transform();
+	void _flip_horizontal();
+	void _flip_vertical();
+	void _rotate(int steps);
+
 protected:
 	void _notification(int p_what);
 	static void _bind_methods();
 	CellOp _get_op_from_cell(const Point2i &p_pos);
-	void _update_transform_buttons(Object *p_button = NULL);
 
 public:
 	HBoxContainer *get_toolbar() const { return toolbar; }
diff --git a/scene/gui/item_list.cpp b/scene/gui/item_list.cpp
index 494995fb85..cb37fa396d 100644
--- a/scene/gui/item_list.cpp
+++ b/scene/gui/item_list.cpp
@@ -36,6 +36,7 @@ void ItemList::add_item(const String &p_item, const Ref<Texture> &p_texture, boo
 
 	Item item;
 	item.icon = p_texture;
+	item.icon_transposed = false;
 	item.icon_region = Rect2i();
 	item.icon_modulate = Color(1, 1, 1, 1);
 	item.text = p_item;
@@ -54,6 +55,7 @@ void ItemList::add_icon_item(const Ref<Texture> &p_item, bool p_selectable) {
 
 	Item item;
 	item.icon = p_item;
+	item.icon_transposed = false;
 	item.icon_region = Rect2i();
 	item.icon_modulate = Color(1, 1, 1, 1);
 	//item.text=p_item;
@@ -124,6 +126,22 @@ Ref<Texture> ItemList::get_item_icon(int p_idx) const {
 	return items[p_idx].icon;
 }
 
+void ItemList::set_item_icon_transposed(int p_idx, const bool p_transposed) {
+
+	ERR_FAIL_INDEX(p_idx, items.size());
+
+	items.write[p_idx].icon_transposed = p_transposed;
+	update();
+	shape_changed = true;
+}
+
+bool ItemList::is_item_icon_transposed(int p_idx) const {
+
+	ERR_FAIL_INDEX_V(p_idx, items.size(), false);
+
+	return items[p_idx].icon_transposed;
+}
+
 void ItemList::set_item_icon_region(int p_idx, const Rect2 &p_region) {
 
 	ERR_FAIL_INDEX(p_idx, items.size());
@@ -416,6 +434,7 @@ void ItemList::set_icon_mode(IconMode p_mode) {
 	update();
 	shape_changed = true;
 }
+
 ItemList::IconMode ItemList::get_icon_mode() const {
 
 	return icon_mode;
@@ -435,10 +454,15 @@ Size2 ItemList::Item::get_icon_size() const {
 
 	if (icon.is_null())
 		return Size2();
-	if (icon_region.has_no_area())
-		return icon->get_size();
 
-	return icon_region.size;
+	Size2 size_result = Size2(icon_region.size).abs();
+	if (icon_transposed) {
+		Size2 size_tmp = size_result;
+		size_result.x = size_tmp.y;
+		size_result.y = size_tmp.x;
+	}
+
+	return size_result;
 }
 
 void ItemList::_gui_input(const Ref<InputEvent> &p_event) {
@@ -1067,10 +1091,14 @@ void ItemList::_notification(int p_what) {
 				if (items[i].disabled)
 					modulate.a *= 0.5;
 
-				if (items[i].icon_region.has_no_area())
-					draw_texture_rect(items[i].icon, draw_rect, false, modulate);
-				else
-					draw_texture_rect_region(items[i].icon, draw_rect, items[i].icon_region, modulate);
+				// If the icon is transposed, we have to swith the size so that it is drawn correctly
+				if (items[i].icon_transposed) {
+					Size2 size_tmp = draw_rect.size;
+					draw_rect.size.x = size_tmp.y;
+					draw_rect.size.y = size_tmp.x;
+				}
+
+				draw_texture_rect_region(items[i].icon, draw_rect, items[i].icon_region, modulate, items[i].icon_transposed);
 			}
 
 			if (items[i].tag_icon.is_valid()) {
@@ -1405,6 +1433,9 @@ void ItemList::_bind_methods() {
 	ClassDB::bind_method(D_METHOD("set_item_icon", "idx", "icon"), &ItemList::set_item_icon);
 	ClassDB::bind_method(D_METHOD("get_item_icon", "idx"), &ItemList::get_item_icon);
 
+	ClassDB::bind_method(D_METHOD("set_item_icon_transposed", "idx", "rect"), &ItemList::set_item_icon_transposed);
+	ClassDB::bind_method(D_METHOD("is_item_icon_transposed", "idx"), &ItemList::is_item_icon_transposed);
+
 	ClassDB::bind_method(D_METHOD("set_item_icon_region", "idx", "rect"), &ItemList::set_item_icon_region);
 	ClassDB::bind_method(D_METHOD("get_item_icon_region", "idx"), &ItemList::get_item_icon_region);
 
diff --git a/scene/gui/item_list.h b/scene/gui/item_list.h
index 58771c1777..acd17986eb 100644
--- a/scene/gui/item_list.h
+++ b/scene/gui/item_list.h
@@ -53,6 +53,7 @@ private:
 	struct Item {
 
 		Ref<Texture> icon;
+		bool icon_transposed;
 		Rect2i icon_region;
 		Color icon_modulate;
 		Ref<Texture> tag_icon;
@@ -133,6 +134,9 @@ public:
 	void set_item_icon(int p_idx, const Ref<Texture> &p_icon);
 	Ref<Texture> get_item_icon(int p_idx) const;
 
+	void set_item_icon_transposed(int p_idx, const bool transposed);
+	bool is_item_icon_transposed(int p_idx) const;
+
 	void set_item_icon_region(int p_idx, const Rect2 &p_region);
 	Rect2 get_item_icon_region(int p_idx) const;