diff --git a/safeeyes/__main__.py b/safeeyes/__main__.py
index 929e1ede..e4e0d9f1 100755
--- a/safeeyes/__main__.py
+++ b/safeeyes/__main__.py
@@ -130,7 +130,7 @@ def main():
     utility.initialize_logging(args.debug)
     utility.initialize_platform()
     config = Config()
-    utility.create_user_stylesheet_if_missing()
+    utility.cleanup_old_user_stylesheet()
 
     if __running():
         logging.info("Safe Eyes is already running")
diff --git a/safeeyes/config/locale/safeeyes.pot b/safeeyes/config/locale/safeeyes.pot
index d9fe78c7..0747768a 100644
--- a/safeeyes/config/locale/safeeyes.pot
+++ b/safeeyes/config/locale/safeeyes.pot
@@ -557,3 +557,7 @@ msgstr ""
 
 msgid "License:"
 msgstr ""
+
+#, python-format
+msgid "Old stylesheet found at '%(old)s', ignoring. For custom styles, create a new stylesheet in '%(new)s' instead."
+msgstr ""
diff --git a/safeeyes/model.py b/safeeyes/model.py
index 2fc5f0e3..d397ffb1 100644
--- a/safeeyes/model.py
+++ b/safeeyes/model.py
@@ -327,8 +327,6 @@ def __init__(self, init=True):
                             self.__user_config, self.__system_config
                         )
                         self.__user_config = self.__system_config
-                        # Update the style sheet
-                        utility.replace_style_sheet()
 
             utility.merge_plugins(self.__user_config)
             self.save()
diff --git a/safeeyes/safeeyes.py b/safeeyes/safeeyes.py
index a43fcb3e..d7f743ef 100644
--- a/safeeyes/safeeyes.py
+++ b/safeeyes/safeeyes.py
@@ -104,12 +104,11 @@ def do_startup(self):
         else:
             self.context["session"] = {"plugin": {}}
 
+        # Initialize the theme
+        self._initialize_styles()
+
         self.break_screen = BreakScreen(
-            self,
-            self.context,
-            self.on_skipped,
-            self.on_postponed,
-            utility.STYLE_SHEET_PATH,
+            self, self.context, self.on_skipped, self.on_postponed
         )
         self.break_screen.initialize(self.config)
         self.plugins_manager = PluginManager()
@@ -166,6 +165,16 @@ def do_activate(self):
         elif self.cli_args.take_break:
             self.take_break()
 
+    def _initialize_styles(self):
+        utility.load_css_file(
+            utility.SYSTEM_STYLE_SHEET_PATH, Gtk.STYLE_PROVIDER_PRIORITY_APPLICATION
+        )
+        utility.load_css_file(
+            utility.CUSTOM_STYLE_SHEET_PATH,
+            Gtk.STYLE_PROVIDER_PRIORITY_USER,
+            required=False,
+        )
+
     def _retry_errored_plugins(self):
         if not self.plugins_manager.needs_retry():
             return
diff --git a/safeeyes/ui/break_screen.py b/safeeyes/ui/break_screen.py
index c385d7f0..3ff43469 100644
--- a/safeeyes/ui/break_screen.py
+++ b/safeeyes/ui/break_screen.py
@@ -43,9 +43,7 @@ class BreakScreen:
     interface.
     """
 
-    def __init__(
-        self, application, context, on_skipped, on_postponed, style_sheet_path
-    ):
+    def __init__(self, application, context, on_skipped, on_postponed):
         self.application = application
         self.context = context
         self.count_labels = []
@@ -64,15 +62,6 @@ def __init__(
         if not self.context["is_wayland"]:
             self.x11_display = Display()
 
-        # Initialize the theme
-        css_provider = Gtk.CssProvider()
-        css_provider.load_from_path(style_sheet_path)
-
-        display = Gdk.Display.get_default()
-        Gtk.StyleContext.add_provider_for_display(
-            display, css_provider, Gtk.STYLE_PROVIDER_PRIORITY_APPLICATION
-        )
-
     def initialize(self, config):
         """Initialize the internal properties from configuration."""
         logging.info("Initialize the break screen")
diff --git a/safeeyes/utility.py b/safeeyes/utility.py
index 7bc8532d..b6f0fe0b 100644
--- a/safeeyes/utility.py
+++ b/safeeyes/utility.py
@@ -19,6 +19,7 @@
 """This module contains utility functions for Safe Eyes and its plugins."""
 
 import errno
+import hashlib
 import inspect
 import importlib
 import json
@@ -38,13 +39,14 @@
 import gi
 
 gi.require_version("Gtk", "4.0")
+gi.require_version("Gdk", "4.0")
+
+from gi.repository import Gdk
 from gi.repository import Gtk
 from gi.repository import GLib
 from gi.repository import GdkPixbuf
 from packaging.version import parse
 
-gi.require_version("Gdk", "4.0")
-
 BIN_DIRECTORY = os.path.dirname(os.path.realpath(__file__))
 HOME_DIRECTORY = os.environ.get("HOME") or os.path.expanduser("~")
 CONFIG_DIRECTORY = os.path.join(
@@ -55,7 +57,10 @@
 CONFIG_FILE_PATH = os.path.join(CONFIG_DIRECTORY, "safeeyes.json")
 CONFIG_RESOURCE = os.path.join(CONFIG_DIRECTORY, "resource")
 SESSION_FILE_PATH = os.path.join(CONFIG_DIRECTORY, "session.json")
-STYLE_SHEET_PATH = os.path.join(STYLE_SHEET_DIRECTORY, "safeeyes_style.css")
+OLD_STYLE_SHEET_PATH = os.path.join(STYLE_SHEET_DIRECTORY, "safeeyes_style.css")
+CUSTOM_STYLE_SHEET_PATH = os.path.join(
+    STYLE_SHEET_DIRECTORY, "safeeyes_custom_style.css"
+)
 SYSTEM_CONFIG_FILE_PATH = os.path.join(BIN_DIRECTORY, "config/safeeyes.json")
 SYSTEM_STYLE_SHEET_PATH = os.path.join(BIN_DIRECTORY, "config/style/safeeyes_style.css")
 LOG_FILE_PATH = os.path.join(HOME_DIRECTORY, "safeeyes.log")
@@ -372,8 +377,32 @@ def merge_configs(new_config, old_config):
     return new_config
 
 
+def sha256sum(filename):
+    """Get the sha256 hash of the given file."""
+    h = hashlib.sha256()
+    b = bytearray(128 * 1024)
+    mv = memoryview(b)
+    with open(filename, "rb", buffering=0) as f:
+        for n in iter(lambda: f.readinto(mv), 0):
+            h.update(mv[:n])
+    return h.hexdigest()
+
+
+def load_css_file(style_sheet_path, priority, required=True):
+    if not os.path.isfile(style_sheet_path):
+        if required:
+            logging.warning("Failed loading required stylesheet")
+        return
+
+    css_provider = Gtk.CssProvider()
+    css_provider.load_from_path(style_sheet_path)
+
+    display = Gdk.Display.get_default()
+    Gtk.StyleContext.add_provider_for_display(display, css_provider, priority)
+
+
 def initialize_safeeyes():
-    """Create the config file and style sheet in XDG_CONFIG_HOME(or
+    """Create the config file in XDG_CONFIG_HOME(or
     ~/.config)/safeeyes directory.
     """
     logging.info("Copy the config files to XDG_CONFIG_HOME(or ~/.config)/safeeyes")
@@ -388,8 +417,6 @@ def initialize_safeeyes():
     shutil.copy2(SYSTEM_CONFIG_FILE_PATH, CONFIG_FILE_PATH)
     os.chmod(CONFIG_FILE_PATH, 0o666)
 
-    create_user_stylesheet_if_missing()
-
     # initialize_safeeyes gets called when the configuration file is not present, which
     # happens just after installation or manual deletion of
     # .config/safeeyes/safeeyes.json file. In these cases, we want to force the creation
@@ -397,15 +424,38 @@ def initialize_safeeyes():
     create_startup_entry(force=True)
 
 
-def create_user_stylesheet_if_missing():
+def cleanup_old_user_stylesheet():
     # Create the XDG_CONFIG_HOME(or ~/.config)/safeeyes/style directory
     if not os.path.isdir(STYLE_SHEET_DIRECTORY):
         mkdir(STYLE_SHEET_DIRECTORY)
 
-    # Copy the new style sheet
-    if not os.path.isfile(STYLE_SHEET_PATH):
-        shutil.copy2(SYSTEM_STYLE_SHEET_PATH, STYLE_SHEET_PATH)
-        os.chmod(STYLE_SHEET_PATH, 0o666)
+    # Delete the old stylesheet, unless it has customizations
+    if os.path.isfile(OLD_STYLE_SHEET_PATH):
+        hash = sha256sum(OLD_STYLE_SHEET_PATH)
+        old_default_versions = [
+            # 2.2.3
+            "fdc2a305613ae4eeb269650452789d35df3df5bdf1c56eb576cd5ebac70a6f09",
+            # 2.1.0 - 2.2.2
+            "fbde048fc234db757461971a7542df43a467869035ca3d05ff9b236ca250e4c5",
+            # 2.0.9
+            "70ca55c12d83ad7a6a4e1c5e7758a38617a43f5d32f28709ede75426d3186713",
+            # 2.0.7 - 2.0.8
+            "7a15f985e0da6d92c8a62d49ce151781e6d423f87e66d205cc1dc4536e369e19",
+            # 2.0.6 and earlier
+            "f26621a883e323ca7685a4adba25027e70daa471e0db4a21c261e6c15caaa5ee",
+        ]
+        if hash in old_default_versions:
+            logging.info("Deleting old stylesheet containing default content")
+            delete(OLD_STYLE_SHEET_PATH)
+        else:
+            # Stylesheet was likely customized, don't delete but warn
+            logging.warning(
+                _(
+                    "Old stylesheet found at '%(old)s', ignoring. For custom styles, "
+                    "create a new stylesheet in '%(new)s' instead.",
+                )
+                % {"old": OLD_STYLE_SHEET_PATH, "new": CUSTOM_STYLE_SHEET_PATH}
+            )
 
 
 def create_startup_entry(force=False):
@@ -517,26 +567,16 @@ def initialize_platform():
 def reset_config():
     # Remove the ~/.config/safeeyes/safeeyes.json and safeeyes_style.css
     delete(CONFIG_FILE_PATH)
-    delete(STYLE_SHEET_PATH)
 
     # Copy the safeeyes.json and safeeyes_style.css
     shutil.copy2(SYSTEM_CONFIG_FILE_PATH, CONFIG_FILE_PATH)
-    shutil.copy2(SYSTEM_STYLE_SHEET_PATH, STYLE_SHEET_PATH)
 
     # Add write permission (e.g. if original file was stored in /nix/store)
     os.chmod(CONFIG_FILE_PATH, 0o666)
-    os.chmod(STYLE_SHEET_PATH, 0o666)
 
     create_startup_entry()
 
 
-def replace_style_sheet():
-    """Replace the user style sheet by system style sheet."""
-    delete(STYLE_SHEET_PATH)
-    shutil.copy2(SYSTEM_STYLE_SHEET_PATH, STYLE_SHEET_PATH)
-    os.chmod(STYLE_SHEET_PATH, 0o666)
-
-
 def initialize_logging(debug):
     """Initialize the logging framework using the Safe Eyes specific
     configurations.