I have downloaded & installed python latest 2.7 version (on date - 16th July). Initially i was unable to install even pip using cmd - python get-pip.py, somehow i managed to installed pip. Then i was unable to install any package using pip. It throws SSL error. Tried multiple ways to install but no go. No proxy or admin issues observed (admin confirmed the same). 

Then i uninstalled & reinstalled 2.7.10 which resolved the issue. 
Please check the attached screenshots and resolve it.

This looks like a pip problem. Please open a bug report at https://github.com/pypa/pip

There is a big chance it is not a direct issue with either python or pip / rather an issue with how current your "openssl" setup is.

As an example, using git I was not able to "pull" from a remote. This git (that also depends on python) has been working for ages. I "fixed" it by getting an updated "global" cacert.pem "chain of trust" installed and now https://... queries were working instantly.

So, did you perhaps, also update your SSL while re-installing/updating python2? (And also note, v2.7.10 is several years old. The latest v2.7 version is 2.7.15).