1978 - LGBT+ / Queer / Gay Pride Flag (1st)
LGBT+ / Queer / Gay Pride Flag (2nd)
1979 - LGBT+ / Queer / Gay Pride Flag (3rd)
1989 - Leather Pride Flag
1994 - Rubber Pride Flag
1995 - Bear Pride Flag
Polyamory Pride Flag
1998 - Bisexual Pride Flag
1999 - Transgender Pride Flag
Lesbian Pride Flag (1st, Labrys, representing feminist action)
Feather Pride Flag
Early 2000s - Straight Ally Pride Flag
2009 - Intersex Pride Flag (1st)
2010 - Pansexual Pride Flag
Asexual Pride Flag
Demisexual Pride Flag
2011 - Genderqueer Pride Flag
Aromantic Pride Flag (1st)
2012 - Genderfluid Pride Flag
Polysexual Pride Flag
2013 - Intersex Pride Flag (2nd)
Graysexual Pride Flag
2013(?) - Autosexual Pride Flag
2013 - Ceterosexual Pride Flag (1st; with heart)
Some time before 2014 - Bigender Pride Flag (1st)
2014 - Nonbinary Pride Flag
Agender Pride Flag
Aromantic Pride Flag (3rd)
Mid-2010s - Gay Man Pride Flag (1st)
2015 - Omnisexual Pride Flag
Queer Pride Flag (1st)
Sapphic Pride Flag (original)
2016 or earlier - Lith Pride Flag
Achillean Pride Flag (original)
2016 - Two-Spirit Pride Flag (1st?)
Queer Pride Flag (2nd?)
Queer Pride Flag (3rd?)
2017 - Philly Pride Flag
2018 - Lesbian Pride Flag (3rd, if you count the lipstick variant, which many didn’t until the late 2010s)
Progress Pride Flag
2019 - Gay Man Pride Flag (3rd)
Important note: The existence of a pride flag does not mean that a word or community were never established beforehand (for example, omnisexual dates back to the 50s/60s!). Additionally, the lack of a flag does not mean something is fake.
This also does not include all variations of (some of) these flags because that would take all night to list.
There is of course WAY MORE than this! But I thought people ought to know just how old or how new some flags are.