diff --git a/src/gfx.cpp b/src/gfx.cpp
index 147a717a85..43a2072d4a 100644
--- a/src/gfx.cpp
+++ b/src/gfx.cpp
@@ -922,6 +922,21 @@ Dimension GetStringBoundingBox(StringID strid, FontSize start_fontsize)
 	return GetStringBoundingBox(buffer, start_fontsize);
 }
 
+/**
+ * Get maximum width of a list of strings.
+ * @param list List of strings, terminated with INVALID_STRING_ID.
+ * @param fontsize Font size to use.
+ * @return Width of longest string within the list.
+ */
+uint GetStringListWidth(const StringID *list, FontSize fontsize)
+{
+	uint width = 0;
+	for (const StringID *str = list; *str != INVALID_STRING_ID; str++) {
+		width = std::max(width, GetStringBoundingBox(*str, fontsize).width);
+	}
+	return width;
+}
+
 /**
  * Get the leading corner of a character in a single-line string relative
  * to the start of the string.
diff --git a/src/gfx_func.h b/src/gfx_func.h
index 882f6482ec..78891e1dc7 100644
--- a/src/gfx_func.h
+++ b/src/gfx_func.h
@@ -148,6 +148,7 @@ static inline void GfxFillRect(const Rect &r, int colour, FillRectMode mode = FI
 Dimension GetStringBoundingBox(const char *str, FontSize start_fontsize = FS_NORMAL);
 Dimension GetStringBoundingBox(const std::string &str, FontSize start_fontsize = FS_NORMAL);
 Dimension GetStringBoundingBox(StringID strid, FontSize start_fontsize = FS_NORMAL);
+uint GetStringListWidth(const StringID *list, FontSize fontsize = FS_NORMAL);
 int GetStringHeight(const char *str, int maxw, FontSize fontsize = FS_NORMAL);
 int GetStringHeight(StringID str, int maxw);
 int GetStringLineCount(StringID str, int maxw);
diff --git a/src/group_gui.cpp b/src/group_gui.cpp
index 5a423a7cde..6b50133880 100644
--- a/src/group_gui.cpp
+++ b/src/group_gui.cpp
@@ -27,6 +27,7 @@
 #include "gui.h"
 #include "group_cmd.h"
 #include "vehicle_cmd.h"
+#include "gfx_func.h"
 
 #include "widgets/group_widget.h"
 
@@ -72,15 +73,21 @@ static const NWidgetPart _nested_group_widgets[] = {
 		/* right part */
 		NWidget(NWID_VERTICAL),
 			NWidget(NWID_HORIZONTAL),
-				NWidget(WWT_TEXTBTN, COLOUR_GREY, WID_GL_GROUP_BY_ORDER), SetMinimalSize(81, 12), SetDataTip(STR_STATION_VIEW_GROUP, STR_TOOLTIP_GROUP_ORDER),
-				NWidget(WWT_DROPDOWN, COLOUR_GREY, WID_GL_GROUP_BY_DROPDOWN), SetMinimalSize(167, 12), SetDataTip(0x0, STR_TOOLTIP_GROUP_ORDER),
-				NWidget(WWT_PANEL, COLOUR_GREY), SetMinimalSize(12, 12), SetResize(1, 0), EndContainer(),
-			EndContainer(),
-			NWidget(NWID_HORIZONTAL),
-				NWidget(WWT_PUSHTXTBTN, COLOUR_GREY, WID_GL_SORT_BY_ORDER), SetMinimalSize(81, 12), SetDataTip(STR_BUTTON_SORT_BY, STR_TOOLTIP_SORT_ORDER),
-				NWidget(WWT_DROPDOWN, COLOUR_GREY, WID_GL_SORT_BY_DROPDOWN), SetMinimalSize(167, 12), SetDataTip(0x0, STR_TOOLTIP_SORT_CRITERIA),
-				NWidget(WWT_DROPDOWN, COLOUR_GREY, WID_GL_FILTER_BY_CARGO), SetMinimalSize(167, 12), SetDataTip(STR_JUST_STRING, STR_TOOLTIP_FILTER_CRITERIA),
-				NWidget(WWT_PANEL, COLOUR_GREY), SetMinimalSize(12, 12), SetResize(1, 0), EndContainer(),
+				NWidget(NWID_VERTICAL),
+					NWidget(WWT_TEXTBTN, COLOUR_GREY, WID_GL_GROUP_BY_ORDER), SetFill(1, 0), SetMinimalSize(0, 12), SetDataTip(STR_STATION_VIEW_GROUP, STR_TOOLTIP_GROUP_ORDER),
+					NWidget(WWT_PUSHTXTBTN, COLOUR_GREY, WID_GL_SORT_BY_ORDER), SetFill(1, 0), SetMinimalSize(0, 12), SetDataTip(STR_BUTTON_SORT_BY, STR_TOOLTIP_SORT_ORDER),
+				EndContainer(),
+				NWidget(NWID_VERTICAL),
+					NWidget(WWT_DROPDOWN, COLOUR_GREY, WID_GL_GROUP_BY_DROPDOWN), SetFill(1, 0), SetMinimalSize(0, 12), SetDataTip(0x0, STR_TOOLTIP_GROUP_ORDER),
+					NWidget(WWT_DROPDOWN, COLOUR_GREY, WID_GL_SORT_BY_DROPDOWN), SetFill(1, 0), SetMinimalSize(0, 12), SetDataTip(0x0, STR_TOOLTIP_SORT_CRITERIA),
+				EndContainer(),
+				NWidget(NWID_VERTICAL),
+					NWidget(WWT_PANEL, COLOUR_GREY), SetMinimalSize(0, 12), SetResize(1, 0), EndContainer(),
+					NWidget(NWID_HORIZONTAL),
+						NWidget(WWT_DROPDOWN, COLOUR_GREY, WID_GL_FILTER_BY_CARGO), SetMinimalSize(0, 12), SetDataTip(STR_JUST_STRING, STR_TOOLTIP_FILTER_CRITERIA),
+						NWidget(WWT_PANEL, COLOUR_GREY), SetMinimalSize(0, 12), SetResize(1, 0), EndContainer(),
+					EndContainer(),
+				EndContainer(),
 			EndContainer(),
 			NWidget(NWID_HORIZONTAL),
 				NWidget(WWT_MATRIX, COLOUR_GREY, WID_GL_LIST_VEHICLE), SetMinimalSize(248, 0), SetMatrixDataTip(1, 0, STR_NULL), SetResize(1, 1), SetFill(1, 0), SetScrollbar(WID_GL_LIST_VEHICLE_SCROLLBAR),
@@ -406,6 +413,20 @@ public:
 				size->height = 4 * resize->height;
 				break;
 
+			case WID_GL_GROUP_BY_DROPDOWN:
+				size->width = GetStringListWidth(this->vehicle_group_by_names) + padding.width;
+				break;
+
+			case WID_GL_SORT_BY_DROPDOWN:
+				size->width = GetStringListWidth(this->vehicle_group_none_sorter_names);
+				size->width = std::max(size->width, GetStringListWidth(this->vehicle_group_shared_orders_sorter_names));
+				size->width += padding.width;
+				break;
+
+			case WID_GL_FILTER_BY_CARGO:
+				size->width = GetStringListWidth(this->cargo_filter_texts) + padding.width;
+				break;
+
 			case WID_GL_MANAGE_VEHICLES_DROPDOWN: {
 				Dimension d = this->GetActionDropdownSize(true, true);
 				d.height += padding.height;
diff --git a/src/vehicle_gui.cpp b/src/vehicle_gui.cpp
index a0388a6c54..c7273a885a 100644
--- a/src/vehicle_gui.cpp
+++ b/src/vehicle_gui.cpp
@@ -1504,18 +1504,23 @@ static const NWidgetPart _nested_vehicle_list[] = {
 	EndContainer(),
 
 	NWidget(NWID_HORIZONTAL),
-		NWidget(WWT_TEXTBTN, COLOUR_GREY, WID_VL_GROUP_ORDER), SetMinimalSize(81, 12), SetFill(0, 1), SetDataTip(STR_STATION_VIEW_GROUP, STR_TOOLTIP_GROUP_ORDER),
-		NWidget(WWT_DROPDOWN, COLOUR_GREY, WID_VL_GROUP_BY_PULLDOWN), SetMinimalSize(167, 12), SetFill(0, 1), SetDataTip(0x0, STR_TOOLTIP_GROUP_ORDER),
-		NWidget(WWT_PANEL, COLOUR_GREY), SetMinimalSize(12, 12), SetFill(1, 1), SetResize(1, 0), EndContainer(),
-	EndContainer(),
-
-	NWidget(NWID_HORIZONTAL),
-		NWidget(WWT_PUSHTXTBTN, COLOUR_GREY, WID_VL_SORT_ORDER), SetMinimalSize(81, 12), SetFill(0, 1), SetDataTip(STR_BUTTON_SORT_BY, STR_TOOLTIP_SORT_ORDER),
-		NWidget(WWT_DROPDOWN, COLOUR_GREY, WID_VL_SORT_BY_PULLDOWN), SetMinimalSize(167, 12), SetFill(0, 1), SetDataTip(0x0, STR_TOOLTIP_SORT_CRITERIA),
-		NWidget(NWID_SELECTION, INVALID_COLOUR, WID_VL_FILTER_BY_CARGO_SEL),
-			NWidget(WWT_DROPDOWN, COLOUR_GREY, WID_VL_FILTER_BY_CARGO), SetMinimalSize(167, 12), SetFill(0, 1), SetDataTip(STR_JUST_STRING, STR_TOOLTIP_FILTER_CRITERIA),
+		NWidget(NWID_VERTICAL),
+			NWidget(WWT_TEXTBTN, COLOUR_GREY, WID_VL_GROUP_ORDER), SetMinimalSize(0, 12), SetFill(1, 0), SetDataTip(STR_STATION_VIEW_GROUP, STR_TOOLTIP_GROUP_ORDER),
+			NWidget(WWT_PUSHTXTBTN, COLOUR_GREY, WID_VL_SORT_ORDER), SetMinimalSize(0, 12), SetFill(1, 0), SetDataTip(STR_BUTTON_SORT_BY, STR_TOOLTIP_SORT_ORDER),
+		EndContainer(),
+		NWidget(NWID_VERTICAL),
+			NWidget(WWT_DROPDOWN, COLOUR_GREY, WID_VL_GROUP_BY_PULLDOWN), SetMinimalSize(0, 12), SetFill(1, 0), SetDataTip(0x0, STR_TOOLTIP_GROUP_ORDER),
+			NWidget(WWT_DROPDOWN, COLOUR_GREY, WID_VL_SORT_BY_PULLDOWN), SetMinimalSize(0, 12), SetFill(1, 0), SetDataTip(0x0, STR_TOOLTIP_SORT_CRITERIA),
+		EndContainer(),
+		NWidget(NWID_VERTICAL),
+			NWidget(WWT_PANEL, COLOUR_GREY), SetMinimalSize(0, 12), SetFill(1, 1), SetResize(1, 0), EndContainer(),
+			NWidget(NWID_HORIZONTAL),
+				NWidget(NWID_SELECTION, INVALID_COLOUR, WID_VL_FILTER_BY_CARGO_SEL),
+					NWidget(WWT_DROPDOWN, COLOUR_GREY, WID_VL_FILTER_BY_CARGO), SetMinimalSize(0, 12), SetFill(0, 0), SetDataTip(STR_JUST_STRING, STR_TOOLTIP_FILTER_CRITERIA),
+				EndContainer(),
+				NWidget(WWT_PANEL, COLOUR_GREY), SetMinimalSize(0, 12), SetFill(1, 1), SetResize(1, 0), EndContainer(),
+			EndContainer(),
 		EndContainer(),
-		NWidget(WWT_PANEL, COLOUR_GREY), SetMinimalSize(12, 12), SetFill(1, 1), SetResize(1, 0), EndContainer(),
 	EndContainer(),
 
 	NWidget(NWID_HORIZONTAL),
@@ -1868,6 +1873,20 @@ public:
 				break;
 			}
 
+			case WID_VL_GROUP_BY_PULLDOWN:
+				size->width = GetStringListWidth(this->vehicle_group_by_names) + padding.width;
+				break;
+
+			case WID_VL_SORT_BY_PULLDOWN:
+				size->width = GetStringListWidth(this->vehicle_group_none_sorter_names);
+				size->width = std::max(size->width, GetStringListWidth(this->vehicle_group_shared_orders_sorter_names));
+				size->width += padding.width;
+				break;
+
+			case WID_VL_FILTER_BY_CARGO:
+				size->width = GetStringListWidth(this->cargo_filter_texts) + padding.width;
+				break;
+
 			case WID_VL_MANAGE_VEHICLES_DROPDOWN: {
 				Dimension d = this->GetActionDropdownSize(this->vli.type == VL_STANDARD, false);
 				d.height += padding.height;