diff --git a/CHANGELOG.md b/CHANGELOG.md
index c2b126b5..6806b92f 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -6,7 +6,7 @@ Release date: UNRELEASED
 
 ### New features and improvements
 
-* ...
+* Added a `--orientation` option to the `pagerotate` command to conditionally rotate the page to a target orientation (thanks to @gatesphere) (#705)
 
 ### Bug fixes
 
diff --git a/tests/test_commands.py b/tests/test_commands.py
index 53fdbd77..414372d5 100644
--- a/tests/test_commands.py
+++ b/tests/test_commands.py
@@ -728,6 +728,28 @@ def test_pagerotate_error(caplog):
     assert "page size is not defined, page not rotated" in caplog.text
 
 
+def test_pagerotate_orientation():
+    doc = vpype_cli.execute("random pagesize a4 pagerotate -o landscape")
+    assert doc.page_size == pytest.approx((1122.5196850393702, 793.7007874015749))
+
+    doc = vpype_cli.execute("random pagesize a4 pagerotate -cw -o landscape")
+    assert doc.page_size == pytest.approx((1122.5196850393702, 793.7007874015749))
+
+    doc = vpype_cli.execute("random pagesize --landscape a4 pagerotate -o portrait")
+    assert doc.page_size == pytest.approx((793.7007874015749, 1122.5196850393702))
+
+    doc = vpype_cli.execute("random pagesize --landscape a4 pagerotate -cw -o portrait")
+    assert doc.page_size == pytest.approx((793.7007874015749, 1122.5196850393702))
+
+
+def test_pagerotate_orientation_error():
+    doc = vpype_cli.execute("random pagesize a4 pagerotate -o portrait")
+    assert doc.page_size == pytest.approx((793.7007874015749, 1122.5196850393702))
+
+    doc = vpype_cli.execute("random pagesize --landscape a4 pagerotate -o landscape")
+    assert doc.page_size == pytest.approx((1122.5196850393702, 793.7007874015749))
+
+
 def test_help(runner):
     res = runner.invoke(cli, "--help")
 
diff --git a/vpype_cli/operations.py b/vpype_cli/operations.py
index eff7aa28..1ddbade8 100644
--- a/vpype_cli/operations.py
+++ b/vpype_cli/operations.py
@@ -11,7 +11,14 @@
 
 from .cli import cli
 from .decorators import global_processor, layer_processor
-from .types import IntegerType, LayerType, LengthType, PageSizeType, multiple_to_layer_ids
+from .types import (
+    ChoiceType,
+    IntegerType,
+    LayerType,
+    LengthType,
+    PageSizeType,
+    multiple_to_layer_ids,
+)
 
 __all__ = (
     "crop",
@@ -662,12 +669,20 @@ def layout(
     is_flag=True,
     help="Rotate clockwise instead of the default counter-clockwise",
 )
+@click.option(
+    "--orientation",
+    "-o",
+    type=ChoiceType(["portrait", "landscape"]),
+    help="Conditionally rotate only if the final orientation matches this option",
+)
 @global_processor
-def pagerotate(document: vp.Document, clockwise: bool):
+def pagerotate(document: vp.Document, clockwise: bool, orientation: str | None):
     """Rotate the page by 90 degrees.
 
     This command rotates the page by 90 degrees counter-clockwise. If the `--clockwise` option
-    is passed, it rotates the page clockwise instead.
+    is passed, it rotates the page clockwise instead.  If the `--orientation` option is given
+    a value of either 'portrait' or 'landscape', the page will only be rotated if the final
+    orientation would match that choice.
 
     Note: if the page size is not defined, an error is printed and the page is not rotated.
     """
@@ -677,6 +692,19 @@ def pagerotate(document: vp.Document, clockwise: bool):
         return document
     w, h = page_size
 
+    # sanity checks
+    if orientation is not None and orientation not in ["portrait", "landscape"]:
+        logging.warning(
+            f"pagerotate: orientation value '{orientation}' not one of 'portrait', 'landscape'"
+        )
+        return document
+
+    # check orientation constraint, and do nothing if target orientation
+    # won't match desired result
+    if (orientation == "portrait" and h > w) or (orientation == "landscape" and w > h):
+        logging.debug("pagerotate: page already in target orientation, page not rotated")
+        return document
+
     if clockwise:
         document.rotate(math.pi / 2)
         document.translate(h, 0)