pip install python-dateutil on OS X 10.11

gistfile1.txt

pip python-dateutil
The directory '/Users/alistra/Library/Caches/pip/http' or its parent directory is not owned by the current user and the cache has been disabled. Please check the permissions and owner of that directory. If executing pip with sudo, you may want sudo's -H flag.
The directory '/Users/alistra/Library/Caches/pip/http' or its parent directory is not owned by the current user and the cache has been disabled. Please check the permissions and owner of that directory. If executing pip with sudo, you may want sudo's -H flag.
/Library/Python/2.7/site-packages/pip/_vendor/requests/packages/urllib3/util/ssl_.py:90: InsecurePlatformWarning: A true SSLContext object is not available. This prevents urllib3 from configuring SSL appropriately and may cause certain SSL connections to fail. For more information, see https://urllib3.readthedocs.org/en/latest/security.html#insecureplatformwarning.
  InsecurePlatformWarning
Collecting python-dateutil
  Downloading python_dateutil-2.4.2-py2.py3-none-any.whl (188kB)
    100% |████████████████████████████████| 192kB 1.7MB/s 
Collecting six>=1.5 (from python-dateutil)
  Downloading six-1.9.0-py2.py3-none-any.whl
Installing collected packages: six, python-dateutil
  Found existing installation: six 1.4.1
    DEPRECATION: Uninstalling a distutils installed project (six) has been deprecated and will be removed in a future version. This is due to the fact that uninstalling a distutils project will only partially uninstall the project.
    Uninstalling six-1.4.1:
Exception:
Traceback (most recent call last):
  File "/Library/Python/2.7/site-packages/pip/basecommand.py", line 223, in main
    status = self.run(options, args)
  File "/Library/Python/2.7/site-packages/pip/commands/install.py", line 297, in run
    root=options.root_path,
  File "/Library/Python/2.7/site-packages/pip/req/req_set.py", line 616, in install
    requirement.uninstall(auto_confirm=True)
  File "/Library/Python/2.7/site-packages/pip/req/req_install.py", line 721, in uninstall
    paths_to_remove.remove(auto_confirm)
  File "/Library/Python/2.7/site-packages/pip/req/req_uninstall.py", line 126, in remove
    renames(path, new_path)
  File "/Library/Python/2.7/site-packages/pip/utils/__init__.py", line 314, in renames
    shutil.move(old, new)
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/shutil.py", line 301, in move
    copy2(src, real_dst)
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/shutil.py", line 131, in copy2
    copystat(src, dst)
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/shutil.py", line 103, in copystat
    os.chflags(dst, st.st_flags)
OSError: [Errno 1] Operation not permitted: '/tmp/pip-w685Lz-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/six-1.4.1-py2.7.egg-info'

Failed to install python-dateutil

Also seeing something similiar under OS X 10.11

Downloading/unpacking python-dateutil>=2.1,<3.0.0 (from botocore==1.0.0b3->awscli)
  Downloading python-dateutil-2.4.2.tar.gz (209kB): 209kB downloaded
  Running setup.py egg_info for package python-dateutil

Downloading/unpacking six>=1.8.0,<2.0.0 (from bcdoc>=0.16.0,<0.17.0->awscli)
  Downloading six-1.9.0.tar.gz
  Running setup.py egg_info for package six

    no previously-included directories found matching 'documentation/_build'
Requirement already up-to-date: pyasn1>=0.1.3 in /Library/Python/2.7/site-packages (from rsa>=3.1.2,<=3.1.4->awscli)
Installing collected packages: python-dateutil, six
  Found existing installation: python-dateutil 1.5
    Uninstalling python-dateutil:
Cleaning up...
Exception:
Traceback (most recent call last):
  File "/Library/Python/2.7/site-packages/pip-1.4.1-py2.7.egg/pip/basecommand.py", line 134, in main
    status = self.run(options, args)
  File "/Library/Python/2.7/site-packages/pip-1.4.1-py2.7.egg/pip/commands/install.py", line 241, in run
    requirement_set.install(install_options, global_options, root=options.root_path)
  File "/Library/Python/2.7/site-packages/pip-1.4.1-py2.7.egg/pip/req.py", line 1294, in install
    requirement.uninstall(auto_confirm=True)
  File "/Library/Python/2.7/site-packages/pip-1.4.1-py2.7.egg/pip/req.py", line 525, in uninstall
    paths_to_remove.remove(auto_confirm)
  File "/Library/Python/2.7/site-packages/pip-1.4.1-py2.7.egg/pip/req.py", line 1639, in remove
    renames(path, new_path)
  File "/Library/Python/2.7/site-packages/pip-1.4.1-py2.7.egg/pip/util.py", line 294, in renames
    shutil.move(old, new)
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/shutil.py", line 298, in move
    copytree(src, real_dst, symlinks=True)
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/shutil.py", line 208, in copytree
    raise Error, errors
Error: [('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/__init__.py', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/__init__.py', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/__init__.py'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/__init__.pyc', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/__init__.pyc', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/__init__.pyc'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/easter.py', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/easter.py', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/easter.py'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/easter.pyc', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/easter.pyc', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/easter.pyc'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/parser.py', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/parser.py', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/parser.py'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/parser.pyc', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/parser.pyc', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/parser.pyc'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/relativedelta.py', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/relativedelta.py', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/relativedelta.py'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/relativedelta.pyc', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/relativedelta.pyc', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/relativedelta.pyc'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/rrule.py', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/rrule.py', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/rrule.py'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/rrule.pyc', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/rrule.pyc', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/rrule.pyc'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/tz.py', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/tz.py', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/tz.py'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/tz.pyc', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/tz.pyc', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/tz.pyc'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/tzwin.py', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/tzwin.py', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/tzwin.py'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/tzwin.pyc', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/tzwin.pyc', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/tzwin.pyc'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/zoneinfo/__init__.py', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/zoneinfo/__init__.py', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/zoneinfo/__init__.py'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/zoneinfo/__init__.pyc', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/zoneinfo/__init__.pyc', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/zoneinfo/__init__.pyc'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/zoneinfo/zoneinfo-2010g.tar.gz', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/zoneinfo/zoneinfo-2010g.tar.gz', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/zoneinfo/zoneinfo-2010g.tar.gz'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/zoneinfo', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/zoneinfo', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil/zoneinfo'"), ('/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil', '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil', "[Errno 1] Operation not permitted: '/tmp/pip-jm5n5n-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/dateutil'")]

Simple because rootless feature now block you from removing anything under /Systems, please disable rootless firstly