diff --git a/docs/README.md b/docs/README.md
index e515304c..59b42ff7 100644
--- a/docs/README.md
+++ b/docs/README.md
@@ -2224,6 +2224,14 @@ httpie_converter (1.0.0)
   httpie_konsole_konverter (httpie.plugins.converter.v1)
 ```
 
+#### `httpie plugins upgrade`
+
+For upgrading already installed plugins, use `httpie plugins upgrade`.
+
+```bash
+$ httpie plugins upgrade httpie-plugin
+```
+
 #### `httpie plugins uninstall`
 
 Uninstall plugins from the isolated plugins directory. If the plugin is not installed
diff --git a/httpie/manager/cli.py b/httpie/manager/cli.py
index eeeb2465..11c63d0a 100644
--- a/httpie/manager/cli.py
+++ b/httpie/manager/cli.py
@@ -14,6 +14,14 @@ COMMANDS = {
                 'help': 'targets to install'
             }
         ],
+        'upgrade': [
+            'Upgrade the given plugins',
+            {
+                'dest': 'targets',
+                'nargs': '+',
+                'help': 'targets to upgrade'
+            }
+        ],
         'uninstall': [
             'Uninstall the given HTTPie plugins.',
             {
diff --git a/httpie/manager/plugins.py b/httpie/manager/plugins.py
index 7760ce23..899e9925 100644
--- a/httpie/manager/plugins.py
+++ b/httpie/manager/plugins.py
@@ -3,15 +3,20 @@ import os
 import subprocess
 import sys
 import textwrap
+import re
+import shutil
 from collections import defaultdict
 from contextlib import suppress
 from pathlib import Path
-from typing import Optional, List
+from typing import Tuple, Optional, List
 
 from httpie.manager.cli import parser, missing_subcommand
 from httpie.compat import importlib_metadata, get_dist_name
 from httpie.context import Environment
 from httpie.status import ExitStatus
+from httpie.utils import as_site
+
+PEP_503 = re.compile(r"[-_.]+")
 
 
 class PluginInstaller:
@@ -68,16 +73,22 @@ class PluginInstaller:
             **options
         )
 
-    def install(self, targets: List[str]) -> Optional[ExitStatus]:
-        self.env.stdout.write(f"Installing {', '.join(targets)}...\n")
-        self.env.stdout.flush()
+    def _install(self, targets: List[str], mode='install', **process_options) -> Tuple[
+        Optional[bytes], ExitStatus
+    ]:
+        pip_args = [
+            'install',
+            f'--prefix={self.dir}',
+            '--no-warn-script-location',
+        ]
+        if mode == 'upgrade':
+            pip_args.append('--upgrade')
 
         try:
-            self.pip(
-                'install',
-                f'--prefix={self.dir}',
-                '--no-warn-script-location',
+            process = self.pip(
+                *pip_args,
                 *targets,
+                **process_options,
             )
         except subprocess.CalledProcessError as error:
             reason = None
@@ -94,7 +105,58 @@ class PluginInstaller:
                 if severity == 'ERROR':
                     reason = message
 
-            return self.fail('install', ', '.join(targets), reason)
+            stdout = error.stdout
+            exit_status = self.fail(mode, ', '.join(targets), reason)
+        else:
+            stdout = process.stdout
+            exit_status = ExitStatus.SUCCESS
+
+        return stdout, exit_status
+
+    def install(self, targets: List[str]) -> ExitStatus:
+        self.env.stdout.write(f"Installing {', '.join(targets)}...\n")
+        self.env.stdout.flush()
+        _, exit_status = self._install(targets)
+        return exit_status
+
+    def _clear_metadata(self, targets: List[str]) -> None:
+        # Due to an outstanding pip problem[0], we have to get rid of
+        # existing metadata for old versions manually.
+        # [0]: https://github.com/pypa/pip/issues/10727
+        result_deps = defaultdict(list)
+        for child in as_site(self.dir).iterdir():
+            if child.suffix in {'.dist-info', '.egg-info'}:
+                name, _, version = child.stem.rpartition('-')
+                result_deps[name].append((version, child))
+
+        for target in targets:
+            name, _, version = target.rpartition('-')
+            name = PEP_503.sub("-", name).lower().replace('-', '_')
+            if name not in result_deps:
+                continue
+
+            for result_version, meta_path in result_deps[name]:
+                if version != result_version:
+                    shutil.rmtree(meta_path)
+
+    def upgrade(self, targets: List[str]) -> ExitStatus:
+        self.env.stdout.write(f"Upgrading {', '.join(targets)}...\n")
+        self.env.stdout.flush()
+
+        raw_stdout, exit_status = self._install(
+            targets,
+            mode='upgrade',
+            stdout=subprocess.PIPE
+        )
+        if not raw_stdout:
+            return exit_status
+
+        stdout = raw_stdout.decode()
+        self.env.stdout.write(stdout)
+
+        installation_line = stdout.splitlines()[-1]
+        if installation_line.startswith('Successfully installed'):
+            self._clear_metadata(installation_line.split()[2:])
 
     def _uninstall(self, target: str) -> Optional[ExitStatus]:
         try:
@@ -178,6 +240,8 @@ class PluginInstaller:
         with enable_plugins(self.dir):
             if action == 'install':
                 status = self.install(args.targets)
+            elif action == 'upgrade':
+                status = self.upgrade(args.targets)
             elif action == 'uninstall':
                 status = self.uninstall(args.targets)
             elif action == 'list':
diff --git a/tests/test_plugins_cli.py b/tests/test_plugins_cli.py
index d644aba7..af4a7746 100644
--- a/tests/test_plugins_cli.py
+++ b/tests/test_plugins_cli.py
@@ -93,6 +93,18 @@ def test_plugins_double_uninstall(httpie_plugins, httpie_plugins_success, dummy_
     )
 
 
+def test_plugins_upgrade(httpie_plugins, httpie_plugins_success, dummy_plugin):
+    httpie_plugins_success("install", dummy_plugin.path)
+
+    # Make a new version of the plugin
+    dummy_plugin.version = '2.0.0'
+    dummy_plugin.build()
+
+    httpie_plugins_success("upgrade", dummy_plugin.path)
+    data = parse_listing(httpie_plugins_success('list'))
+    assert data[dummy_plugin.name]['version'] == '2.0.0'
+
+
 def test_broken_plugins(httpie_plugins, httpie_plugins_success, dummy_plugin, broken_plugin):
     httpie_plugins_success("install", dummy_plugin.path, broken_plugin.path)