diff --git a/tests/unit/api/test_settings.py b/tests/unit/api/test_settings.py
index ead9dc0a0..3f488c7ba 100644
--- a/tests/unit/api/test_settings.py
+++ b/tests/unit/api/test_settings.py
@@ -151,3 +151,21 @@ def ask_question(*args, **kwargs):
     mocker.patch("vimiv.api.prompt.ask_question", ask_question)
 
     assert bool(prompt_setting) == answer
+
+
+def test_set_order_setting():
+    o = settings.OrderSetting("order", "alphabetical")
+    o.value = "alphabetical-desc"
+    assert o.value == "alphabetical-desc"
+
+
+def test_set_order_setting_non_str():
+    o = settings.OrderSetting("order", "alphabetical")
+    with pytest.raises(ValueError, match="must be one of"):
+        o.value = 1
+
+
+def test_set_order_setting_non_valid():
+    o = settings.OrderSetting("order", "alphabetical")
+    with pytest.raises(ValueError, match="must be one of"):
+        o.value = "invalid"
diff --git a/tests/unit/utils/test_files.py b/tests/unit/utils/test_files.py
index 041e9de10..a3007b50d 100644
--- a/tests/unit/utils/test_files.py
+++ b/tests/unit/utils/test_files.py
@@ -87,12 +87,6 @@ def test_listdir_wrapper_returns_abspath(mocker):
     assert files.listdir("directory") == expected
 
 
-def test_listdir_wrapper_sort(mocker):
-    mocker.patch("os.listdir", return_value=["b.txt", "a.txt"])
-    mocker.patch("os.path.abspath", return_value="")
-    assert files.listdir("directory") == ["a.txt", "b.txt"]
-
-
 def test_listdir_wrapper_remove_hidden(mocker):
     mocker.patch("os.listdir", return_value=[".dotfile.txt", "a.txt"])
     mocker.patch("os.path.abspath", return_value="")
@@ -122,6 +116,27 @@ def test_images_supported(mocker):
     assert not directories
 
 
+@pytest.mark.parametrize(
+    "input_img, input_dir, sorted_img, sorted_dir",
+    (
+        (
+            ["a.j", "c.j", "b.j"],
+            ["a", "c", "b"],
+            ["a.j", "b.j", "c.j"],
+            ["a", "b", "c"],
+        ),
+        (
+            ["a2.j", "a3.j", "a1.j"],
+            ["a2", "a3", "a1"],
+            ["a1.j", "a2.j", "a3.j"],
+            ["a1", "a2", "a3"],
+        ),
+    ),
+)
+def test_order(input_img, input_dir, sorted_img, sorted_dir):
+    assert files.order(input_img, input_dir) == (sorted_img, sorted_dir)
+
+
 def test_tar_gz_not_an_image(tmp_path):
     """Test if is_image for a tar.gz returns False.
 
diff --git a/tests/unit/utils/test_utils.py b/tests/unit/utils/test_utils.py
index 3a08ae85f..7a42874fb 100644
--- a/tests/unit/utils/test_utils.py
+++ b/tests/unit/utils/test_utils.py
@@ -332,3 +332,19 @@ def test_is_hex_true(text):
 @pytest.mark.parametrize("text", ("00x234", "0xGC7", "not-hex", "A-67", "a:9e"))
 def test_is_hex_false(text):
     assert not utils.is_hex(text)
+
+
+@pytest.mark.parametrize(
+    "input_list, sorted_list",
+    (
+        (["a100a", "a10a", "a1a"], ["a1a", "a10a", "a100a"]),
+        (
+            ["a10a1a", "a1a10a", "a10a10a", "a1a1a"],
+            ["a1a1a", "a1a10a", "a10a1a", "a10a10a"],
+        ),
+        (["100", "50", "10", "20"], ["10", "20", "50", "100"]),
+        (["aa", "a", "aaa"], ["a", "aa", "aaa"]),
+    ),
+)
+def test_natural_sort(input_list, sorted_list):
+    assert sorted(input_list, key=utils.natural_sort) == sorted_list
diff --git a/vimiv/api/settings.py b/vimiv/api/settings.py
index 36f4a7fcd..31149b411 100644
--- a/vimiv/api/settings.py
+++ b/vimiv/api/settings.py
@@ -13,12 +13,13 @@
 import abc
 import contextlib
 import enum
-from typing import Any, Dict, ItemsView, List
+import os
+from typing import Any, Dict, ItemsView, List, Callable, Tuple
 
 from PyQt5.QtCore import QObject, pyqtSignal
 
 from vimiv.api import prompt
-from vimiv.utils import clamp, AbstractQObjectMeta, log, customtypes
+from vimiv.utils import clamp, AbstractQObjectMeta, log, customtypes, natural_sort
 
 
 _storage: Dict[str, "Setting"] = {}
@@ -315,8 +316,51 @@ def __str__(self) -> str:
         return "String"
 
 
-# Initialize all settings
+class OrderSetting(Setting):
+    """Stores an ordering setting."""
+
+    typ = str
+
+    ORDER_TYPES: Dict[str, Tuple[Callable[..., Any], bool]] = {
+        "alphabetical": (os.path.basename, False),
+        "alphabetical-desc": (os.path.basename, True),
+        "natural": (natural_sort, False),
+        "natural-desc": (natural_sort, True),
+        "recently-modify-first": (os.path.getmtime, False),
+        "recently-modify-last": (os.path.getmtime, True),
+    }
+
+    def __init__(
+        self,
+        *args: Any,
+        additional_order_types: Dict[str, Tuple[Callable[..., Any], bool]] = None,
+        **kwargs: Any,
+    ):
+        super().__init__(*args, **kwargs)
+        self.order_types = dict(self.ORDER_TYPES)
+        if additional_order_types:
+            self.order_types.update(additional_order_types)
+
+    def convert(self, value: str) -> str:
+        if value not in self.order_types:
+            raise ValueError(f"Option must be one of {', '.join(self.ORDER_TYPES)}")
+        return value
+
+    def get_para(self) -> Tuple[Callable[..., Any], bool]:
+        """Returns the ordering parameters according to the current set value."""
+        try:
+            return self.order_types[self.value]
+        except KeyError:
+            raise ValueError(f"Option must be one of {', '.join(self.ORDER_TYPES)}")
 
+    def suggestions(self) -> List[str]:
+        return [str(value) for value in self.order_types]
+
+    def __str__(self) -> str:
+        return "Order"
+
+
+# Initialize all settings
 monitor_fs = BoolSetting(
     "monitor_filesystem",
     True,
@@ -333,6 +377,24 @@ def __str__(self) -> str:
 read_only = BoolSetting(
     "read_only", False, desc="Disable any commands that are able to edit files on disk"
 )
+image_order = OrderSetting(
+    "image_order",
+    "alphabetical",
+    desc="Set image ordering.",
+    additional_order_types={
+        "smallest-first": (os.path.getsize, False),
+        "largest-first": (os.path.getsize, True),
+    },
+)
+directory_order = OrderSetting(
+    "directory_order",
+    "alphabetical",
+    desc="Set directory ordering.",
+    additional_order_types={
+        "smallest-first": (lambda e: len(os.listdir(e)), True),
+        "largest-first": (lambda e: len(os.listdir(e)), False),
+    },
+)
 
 
 class command:  # pylint: disable=invalid-name
diff --git a/vimiv/api/working_directory.py b/vimiv/api/working_directory.py
index 08203d35b..ace734caa 100644
--- a/vimiv/api/working_directory.py
+++ b/vimiv/api/working_directory.py
@@ -109,6 +109,8 @@ def __init__(self) -> None:
         self._directories: List[str] = []
 
         settings.monitor_fs.changed.connect(self._on_monitor_fs_changed)
+        settings.image_order.changed.connect(self._reload_directory)
+        settings.directory_order.changed.connect(self._reload_directory)
         # TODO Fix upstream and open PR
         self.directoryChanged.connect(self._reload_directory)  # type: ignore
         self.fileChanged.connect(self._on_file_changed)  # type: ignore
@@ -219,12 +221,12 @@ def _get_content(self, directory: str) -> Tuple[List[str], List[str]]:
         """Get supported content of directory.
 
         Returns:
-            images: List of images inside the directory.
-            directories: List of directories inside the directory.
+            images: Ordered list of images inside the directory.
+            directories: Ordered list of directories inside the directory.
         """
         show_hidden = settings.library.show_hidden.value
         paths = files.listdir(directory, show_hidden=show_hidden)
-        return files.supported(paths)
+        return files.order(*files.supported(paths))
 
 
 handler = cast(WorkingDirectoryHandler, None)
diff --git a/vimiv/utils/__init__.py b/vimiv/utils/__init__.py
index 02cf77c39..92d9e8a5c 100644
--- a/vimiv/utils/__init__.py
+++ b/vimiv/utils/__init__.py
@@ -526,3 +526,15 @@ def stop_all(cls):
         """Stop all running throttles."""
         for throttle in cls.throttles:
             throttle.stop()
+
+
+def natural_sort(text: str) -> typing.List[typing.Union[str, int]]:
+    """Key function for natural sort.
+
+    Credits to https://stackoverflow.com/a/5967539/5464989
+    """
+
+    def convert(t: str) -> typing.Union[str, int]:
+        return int(t) if t.isdigit() else t
+
+    return [convert(c) for c in re.split(r"(\d+)", text)]
diff --git a/vimiv/utils/files.py b/vimiv/utils/files.py
index 7ccbcb375..832e9cfd6 100644
--- a/vimiv/utils/files.py
+++ b/vimiv/utils/files.py
@@ -15,6 +15,8 @@
 
 from vimiv.utils import imagereader
 
+from vimiv import api
+
 
 ImghdrTestFuncT = Callable[[bytes, Optional[BinaryIO]], bool]
 
@@ -26,13 +28,18 @@ def listdir(directory: str, show_hidden: bool = False) -> List[str]:
         directory: Directory to check for files in via os.listdir(directory).
         show_hidden: Include hidden files in output.
     Returns:
-        Sorted list of files in the directory with their absolute path.
+        List of files in the directory with their absolute path.
     """
     directory = os.path.abspath(os.path.expanduser(directory))
+    order_function, reverse = api.settings.image_order.get_para()
     return sorted(
-        os.path.join(directory, path)
-        for path in os.listdir(directory)
-        if show_hidden or not path.startswith(".")
+        [
+            os.path.join(directory, path)
+            for path in os.listdir(directory)
+            if show_hidden or not path.startswith(".")
+        ],
+        key=order_function,
+        reverse=reverse,
     )
 
 
@@ -55,6 +62,24 @@ def supported(paths: Iterable[str]) -> Tuple[List[str], List[str]]:
     return images, directories
 
 
+def order(images: List[str], directories: List[str]) -> Tuple[List[str], List[str]]:
+    """Orders images and directories according to the settings.
+
+    Args:
+        files: Tuple of list of images and list of directories.
+    Returns:
+        images: Ordered list of images.
+        directories: Orderd list of directories.
+    """
+
+    image_order, image_reverse = api.settings.image_order.get_para()
+    directory_order, directory_reverse = api.settings.directory_order.get_para()
+    images = sorted(images, key=image_order, reverse=image_reverse)
+    directories = sorted(directories, key=directory_order, reverse=directory_reverse)
+
+    return images, directories
+
+
 def get_size(path: str) -> str:
     """Get the size of a path in human readable format.