Were/are Boomer parents cool? My parents were pretty standard issue lower middle class Boomers (with mental illness thrown in) and so were the vast majority of my friends’ parents, though largely without my parents’ mental illness concerns. None of them really struck me as particularly cool or especially uncool.
Depends a lot on how old the parents were. The early boomers from 1948-1956 had parents that lived through the Great Depression. Not a great time to develop coolness. The later boomers from 1956-1964 had war years parents who saw a rapidly changing world and were much cooler. But plenty of other factors were at play, economic status, education, religion, region. There was some of everything, but a large portion of the uncool who didn’t like new-fangled ways of doing things.
Did we have the same dad? 
Mine flew in the military (and then went on to be a commercial pilot), had an awesome stereo system and great taste in music (to which I owe my musical tastes), had a cute little red convertible (that I got to drive in college), and we had a pretty cool house that he helped design and build with an architect friend of his.
Only thing though, unlike you…I didn’t inherit the stereo, nor the car, or the house for that matter (he sold it years before he retired). I did get his cool black cowboy hat that he always wore up skiing though…it was his “signature” hat that everyone knew him by up at the mountain. He said it kept the snow off his neck, but I think he thought it was pretty cool (it was, and he looked great in it).
My parents are leftie hippie-ish university lecturers (now retired), while most of my friends’ parents were more straight-laced business types, so in that respect they were more cool. (My father was notorious even amongst his colleagues for “dressing like a student,” as they said.) They were certainly more relaxed than most of my friends’ parents about things like drinking or staying out late.
On the other hand they were and are not “culturally cool”. They only listen to classical music and don’t really partake of popular culture.
Mine, for the most part, were not cool though occasionally there would be cool traits. They were very tolerant of me listening (back in the late '60s and '70s) to what is now classic rock but at the same time my dad was bloody strict and my mom, in other circumstances, might have been eccentrically artistic. I believe that she invented the concept of “what will people think?”
My dad was an RCAF pilot in WW II and I’ve got some photos of him and his buddies standing together jauntily in front of Berlin ruins immediately post-war, in their battle-dress uniforms with their service pistols visible at their hips.
I was a late arrival (born when my dad was 40) and the difference between my dad and the guy in the photos was almost incomprehensible; he had become almost humourless, staid, conservative and bloody strict.
He and my mom bickered constantly and it was like living with George Constanza’s parents in Seinfeld, only unfunny. I think that my dad had the time of his life in the war while at the same time getting high-functioning PTSD and marrying the wrong woman.
So, not particularly cool.
HELL NO!
My parents were strictly from Squaresville!
My parents defined uncool.
Both grew up on poor farms, and while my mom’s was poor my father grew up in abject poverty. My mom says some years she only two skirts, one for school and the other for church. My father had nothing.
As conservative Mormons, then anything cool would be evil including rock music, outside activities and anything liberal. My father was a John Birch Republican and my mother believed that the only thing good in the world was Mormonism.
And then my dad was extremely abusive and my mom was a battered wife, so even if they had been cool, they wouldn’t have been.
Completely boring and normal. My stepfather was a bartender and my mother worked in a state office. They didn’t have parties and they rarely went out, almost to the point of being antisocial. My mother loved music, but my stepfather barely tolerated it. They drove boring cars, and the only exciting vacation was in 1959, when we drove the Alcan Highway to Montana to see family.
Not even close to cool. Quite straight-laced, tho Dad was a tad less so than Mom.
The cool one was my maternal grandmother. When I was in my late teens/early 20s, she’d buy bodice-rippers at a local thrift store, then pass them on to me saying “This one has a lot of good parts…” My mother would have been aghast!
No, neither of my parents would qualify as being particularly cool, at least as I have known them. But I suspect that my dad might have been pretty cool when he was younger. He was a talented swimmer. Athleticism generally buys you some cool points.
My father smoked all of the weed. Like, all of it. Of course, this was the Reagan administration and I was “educated” in the DARE program, so I thought being near him while he toked would lead to addiction and madness.
My mother would sit at the record player with me and sing along to Fleetwood Mac, Led Zeppelin, yada yada, and would take me to the head shop with her to by incense.
I mean I guess. My dad was NFL, and then a physics professor, and my mom was an artist who sold African trade beads and hung out with Willie Nelson, Waylon Jennings, the whole ‘outlaw’ crowd. Ray Wylie Hubbard used to babysit us.
But he was violently abusive, and she was a checked-out toxic narcissist.