How to completely upgrade SSL on Mac OS Sierra?

Question

OpenSSL

When installing packages via pip, nothing comes out recently,
for example -
pip install django
Collecting django
Could not fetch URL https://pypi.python.org/simple/django/: There was a problem confirming the ssl certificate: [SSL: TLSV1_ALERT_PROTOCOL_VERSION ] tlsv1 alert protocol version (_ssl.c:645) - skipping
Could not find a version that satisfies the requirement django (from versions: )
No matching distribution found for django
ssl version - 'OpenSSL 0.9.8zh 14 Jan 2016'
updated via brew ->
brew update
brew install openssl
Python still sees OpenSSL 0.9.8zh 14 Jan 2016'
and if > openssl version -OpenSSL 1.0.2o 27 Mar 2018