diff --git a/pip/basecommand.py b/pip/basecommand.py
index 2f081253089..4508963b929 100644
--- a/pip/basecommand.py
+++ b/pip/basecommand.py
@@ -16,7 +16,7 @@
 from pip.baseparser import ConfigOptionParser, UpdatingDefaultsHelpFormatter
 from pip.status_codes import (SUCCESS, ERROR, UNKNOWN_ERROR, VIRTUALENV_NOT_FOUND,
                               PREVIOUS_BUILD_DIR_ERROR)
-from pip.util import get_prog
+from pip.util import get_prog, latest_version_check
 
 
 __all__ = ['Command']
@@ -115,6 +115,10 @@ def main(self, args):
         else:
             log_fp = None
 
+        # Check if we're using the latest version of pip available
+        if not options.disable_version_check:
+            latest_version_check(session=self._build_session(options))
+
         exit = SUCCESS
         store_log = False
         try:
diff --git a/pip/cmdoptions.py b/pip/cmdoptions.py
index 1cc4811a18f..bffd90dec97 100644
--- a/pip/cmdoptions.py
+++ b/pip/cmdoptions.py
@@ -304,6 +304,13 @@ def make(self):
     default=False,
     help="Don't clean up build directories.")
 
+disable_version_check = OptionMaker(
+    "--disable-version-check",
+    dest="disable_version_check",
+    action="store_true",
+    default=False,
+    help="Don't check PyPI for new versions of pip.")
+
 
 ##########
 # groups #
@@ -327,6 +334,7 @@ def make(self):
         skip_requirements_regex,
         exists_action,
         cert,
+        disable_version_check,
         ]
     }
 
diff --git a/pip/util.py b/pip/util.py
index 58336e59e4e..2f751a3ee10 100644
--- a/pip/util.py
+++ b/pip/util.py
@@ -1,3 +1,5 @@
+import datetime
+import json
 import sys
 import shutil
 import os
@@ -717,3 +719,65 @@ def is_prerelease(vers):
 
     parsed = version._normalized_key(normalized)
     return any([any([y in set(["a", "b", "c", "rc", "dev"]) for y in x]) for x in parsed])
+
+
+def latest_version_check(session, frequency=7 * 24 * 60 * 60):
+    """
+    Attempt to determine if we're using the latest version of pip or not. Keeps
+    a small state file stored in ~/.pip/ to store when the last time we checked
+    was and what the version was.
+    """
+    pypi_version = None
+
+    try:
+        import pip  # imported here to prevent circular imports
+
+        current_time = datetime.datetime.utcnow()
+
+        fmt = "%Y-%m-%dT%H:%M:%S"
+        statefile_path = os.path.expanduser("~/.pip/versioncheck")
+
+        # Load the existing state
+        try:
+            with open(statefile_path) as statefile:
+                state = json.load(statefile)
+        except (IOError, ValueError):
+            state = {}
+
+        # Determine if we need to refresh the state
+        if "last-check" in state and "version" in state:
+            last_check = datetime.datetime.strptime(state["last-check"], fmt)
+            if (current_time - last_check).total_seconds() < frequency:
+                pypi_version = state["version"]
+
+        # Refresh the version if we need to
+        if pypi_version is None:
+            resp = session.get("https://pypi.python.org/pypi/pip/json",
+                headers={"Accept": "application/json"},
+            )
+            resp.raise_for_status()
+            pypi_version = resp.json()["info"]["version"]
+
+        # Determine if our pypi_version is older
+        need_update = (pkg_resources.parse_version(pip.__version__)
+                            < pkg_resources.parse_version(pypi_version))
+        if need_update:
+            logger.warn(
+                "You are using pip version %s, however version %s is "
+                "available. You should consider upgrading via the pip install "
+                "--upgrade pip command." % (pip.__version__, pypi_version))
+
+        # Attempt to write out our version check file
+        with open(statefile_path, "w") as statefile:
+            json.dump(
+                {
+                    "last-check": current_time.strftime(fmt),
+                    "pypi_version": pypi_version,
+                },
+                statefile,
+            )
+    except Exception:
+        logger.debug(
+            "There was an error checking the latest version of pip",
+            exc_info=True,
+        )
diff --git a/tests/unit/test_basecommand.py b/tests/unit/test_basecommand.py
index 864510f9283..67e07fdac2f 100644
--- a/tests/unit/test_basecommand.py
+++ b/tests/unit/test_basecommand.py
@@ -6,9 +6,15 @@
 class FakeCommand(Command):
     name = 'fake'
     summary = name
+
     def __init__(self, error=False):
         self.error = error
         super(FakeCommand, self).__init__()
+
+    def main(self, args):
+        args.append("--disable-version-check")
+        return super(FakeCommand, self).main(args)
+
     def run(self, options, args):
         logger.info("fake")
         if self.error: