diff --git a/Clocker/Menu Bar/StatusContainerView.swift b/Clocker/Menu Bar/StatusContainerView.swift
index d3ca6b5..c0cfa2c 100644
--- a/Clocker/Menu Bar/StatusContainerView.swift	
+++ b/Clocker/Menu Bar/StatusContainerView.swift	
@@ -5,18 +5,22 @@ import Cocoa
 func bufferCalculatedWidth() -> Int {
     var totalWidth = 55
 
-    if DataStore.shared().shouldShowDateInMenubar() {
-        totalWidth += 8
+    if DataStore.shared().shouldShowDayInMenubar() {
+        totalWidth += 12
     }
 
     if DataStore.shared().shouldDisplay(.twelveHour) {
-        totalWidth += 18
+        totalWidth += 20
     }
 
     if DataStore.shared().shouldDisplay(.seconds) {
         totalWidth += 15
     }
 
+    if DataStore.shared().shouldShowDateInMenubar() {
+        totalWidth += 20
+    }
+
     return totalWidth
 }
 
@@ -24,12 +28,12 @@ func compactWidth(for timezone: TimezoneData) -> Int {
     var totalWidth = 55
     let timeFormat = timezone.timezoneFormat()
 
-    if DataStore.shared().shouldShowDateInMenubar() {
-        totalWidth += 8
+    if DataStore.shared().shouldShowDayInMenubar() {
+        totalWidth += 12
     }
 
     if timeFormat == DateFormat.twelveHour || timeFormat == DateFormat.twelveHourWithSeconds {
-        totalWidth += 18
+        totalWidth += 20
     } else if timeFormat == DateFormat.twentyFourHour || timeFormat == DateFormat.twentyFourHourWithSeconds {
         totalWidth += 0
     }
@@ -39,6 +43,10 @@ func compactWidth(for timezone: TimezoneData) -> Int {
         totalWidth += 15
     }
 
+    if DataStore.shared().shouldShowDateInMenubar() {
+        totalWidth += 20
+    }
+
     return totalWidth
 }
 
diff --git a/Clocker/Overall App/DataStore.swift b/Clocker/Overall App/DataStore.swift
index 38c7f23..f2b1ee7 100644
--- a/Clocker/Overall App/DataStore.swift	
+++ b/Clocker/Overall App/DataStore.swift	
@@ -21,7 +21,8 @@ class DataStore: NSObject {
     private static var sharedStore = DataStore(with: UserDefaults.standard)
     private var userDefaults: UserDefaults!
 
-    // Since this pref can accessed every second, let's cache this
+    // Since these pref can accessed every second, let's cache this
+    private var shouldDisplayDayInMenubar: Bool = false
     private var shouldDisplayDateInMenubar: Bool = false
 
     class func shared() -> DataStore {
@@ -31,7 +32,8 @@ class DataStore: NSObject {
     init(with defaults: UserDefaults) {
         super.init()
         userDefaults = defaults
-        shouldDisplayDateInMenubar = shouldDisplay(.dayInMenubar)
+        shouldDisplayDayInMenubar = shouldDisplay(.dayInMenubar)
+        shouldDisplayDateInMenubar = shouldDisplay(.dateInMenubar)
     }
 
     func timezones() -> [Data] {
@@ -43,7 +45,15 @@ class DataStore: NSObject {
     }
 
     func updateDayPreference() {
-        shouldDisplayDateInMenubar = shouldDisplay(.dayInMenubar)
+        shouldDisplayDayInMenubar = shouldDisplay(.dayInMenubar)
+    }
+
+    func updateDateInPreference() {
+        shouldDisplayDateInMenubar = shouldDisplay(.dateInMenubar)
+    }
+
+    func shouldShowDayInMenubar() -> Bool {
+        return shouldDisplayDayInMenubar
     }
 
     func shouldShowDateInMenubar() -> Bool {
diff --git a/Clocker/Panel/Data Layer/TimezoneDataOperations.swift b/Clocker/Panel/Data Layer/TimezoneDataOperations.swift
index 18a24ed..fed6044 100644
--- a/Clocker/Panel/Data Layer/TimezoneDataOperations.swift	
+++ b/Clocker/Panel/Data Layer/TimezoneDataOperations.swift	
@@ -35,13 +35,23 @@ extension TimezoneDataOperations {
     func compactMenuHeader() -> String {
         var subtitle = CLEmptyString
 
-        let shouldDayBeShown = DataStore.shared().shouldShowDateInMenubar()
+        let shouldDayBeShown = DataStore.shared().shouldShowDayInMenubar()
 
         if shouldDayBeShown {
             let substring = date(with: 0, displayType: CLDateDisplayType.menuDisplay)
             subtitle.append(substring)
         }
 
+        let shouldDateBeShown = DataStore.shared().shouldShowDateInMenubar()
+        if shouldDateBeShown {
+            let date = Date().formatter(with: "MMM d", timeZone: dataObject.timezone())
+            if subtitle.isEmpty == false {
+                subtitle.append(" \(date)")
+            } else {
+                subtitle.append("\(date)")
+            }
+        }
+
         subtitle.isEmpty ? subtitle.append(time(with: 0)) : subtitle.append(" \(time(with: 0))")
 
         return subtitle
@@ -53,8 +63,8 @@ extension TimezoneDataOperations {
         let dataStore = DataStore.shared()
 
         let shouldCityBeShown = dataStore.shouldDisplay(.placeInMenubar)
-        let shouldDayBeShown = dataStore.shouldShowDateInMenubar()
-        let shouldDateBeShown = dataStore.shouldDisplay(.dateInMenubar)
+        let shouldDayBeShown = dataStore.shouldShowDayInMenubar()
+        let shouldDateBeShown = dataStore.shouldShowDateInMenubar()
 
         if shouldCityBeShown {
             if let address = dataObject.formattedAddress, address.isEmpty == false {
diff --git a/Clocker/Preferences/Appearance/AppearanceViewController.swift b/Clocker/Preferences/Appearance/AppearanceViewController.swift
index f05bbda..a205f48 100644
--- a/Clocker/Preferences/Appearance/AppearanceViewController.swift
+++ b/Clocker/Preferences/Appearance/AppearanceViewController.swift
@@ -250,6 +250,7 @@ class AppearanceViewController: ParentViewController {
     }
 
     @IBAction func displayDateInMenubarAction(_: Any) {
+        DataStore.shared().updateDateInPreference()
         updateStatusItem()
     }
 
@@ -288,6 +289,6 @@ class AppearanceViewController: ParentViewController {
     // We don't support showing day or date in the menubar for compact mode yet.
     // Disable those options to let the user know.
     private func updateMenubarControls(_ isEnabled: Bool) {
-        [includePlaceNameControl, includeDateInMenubarControl].forEach { $0?.isEnabled = isEnabled }
+        [includePlaceNameControl].forEach { $0?.isEnabled = isEnabled }
     }
 }