Early 1990's, Russia (i.redd.it)

6454 202 comments DCCXXVIII r/OldSchoolCool
59 1 comments deathakissaway r/OldSchoolCool
34 6 comments nietsllah r/OldSchoolCool
24 6 comments Sh1fty3yedD0g r/OldSchoolCool
3335 69 comments AstrologicalSin r/OldSchoolCool
55 7 comments mjomark r/OldSchoolCool
42 12 comments kittykween611 r/OldSchoolCool
30 2 comments RipplingShore r/OldSchoolCool
13 2 comments bilbodoyle96 r/OldSchoolCool
21 0 comments nedelbach r/OldSchoolCool
15 1 comments sresendes73 r/OldSchoolCool
8 0 comments ringoandgibby r/OldSchoolCool
11 8 comments ConsumerTimeCapsule r/OldSchoolCool
14 0 comments JupiterUnleashed r/OldSchoolCool
16 2 comments thebeanpole16 r/OldSchoolCool
6 0 comments mangosplumsgrapes r/OldSchoolCool

Virginia Bell, 1950s (ist3-1.filesor.com)

154 30 comments joeclark5 r/OldSchoolCool
178 6 comments a_bitch_on_a_mission r/OldSchoolCool
57 2 comments mangosplumsgrapes r/OldSchoolCool
10 0 comments WaterMelonE0001 r/OldSchoolCool
8 1 comments HeWhoCannotBeArsed r/OldSchoolCool
3 0 comments PrettyPandaPrincess r/OldSchoolCool
2 0 comments derpywaffle24 r/OldSchoolCool
50 4 comments K1nsey6 r/OldSchoolCool

Quadricycle c.1894 (vergue.com)

32 1 comments highcontrastgrey r/OldSchoolCool
49 16 comments kaylacactus r/OldSchoolCool
51 5 comments SilentWalrus92 r/OldSchoolCool
238 9 comments Bolinas99 r/OldSchoolCool
17 1 comments god-of_tits-and_wine r/OldSchoolCool
3 6 comments iaxeuanswer r/OldSchoolCool

Helen Mirren - 1960's (i.redd.it)

191 23 comments Anton_Tobias r/OldSchoolCool
6 0 comments Dannyguard r/OldSchoolCool

Vintage Harley 1904 (i.redd.it)

35 2 comments K1nsey6 r/OldSchoolCool
197 5 comments no_problemo r/OldSchoolCool

Betty White (1957) (i.redd.it)

1274 23 comments KinneyBoi r/OldSchoolCool