23 Old School Cool Pics of Dads and Grandpas in the '20s and '30s

Carly Tennes Published 06/16/2024 in wow

Long before they earned the ever-coveted titles of "dad" and "grandpa," our paternal figures were way cooler than any of us realize, sporting three-piece suits, kicking their loafers on the hood of old-timey vehicles, and even piloting airplanes. Don't believe it? Just take a look back at some of the most iconic photos that have passed down from generation to generation.

From a tough-as-nails biker to the sharpest-dressed man on Michigan Avenue, here are 23 sepia-faded snaps of our dads and grandpas from the '20s and '30s that prove they were always the coolest guys around.

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1.
“My great grandpa in the 1920’s.”
2.
“My Great Grandpa looking fly in the 20s.”
3.
“My grandpa played at speakeasies in the 20s.”
4.
“My Great-Grandpa 1920s.”
5.
“Grandpa was ripped - 1920’s.”
6.
“Great grandpa, going for a bike ride in a three piece suit (1920s).”
7.
"My Dad's late 1920-30's."
8.
“My Grandpa in the 30s looking cooler than I could ever hope to be.”
9.
“My grandfather in the 1930s. An Italian immigrant and worked in the coal mines of western Pennsylvania.”
10.
“My grandfather circa 1930s beginning a line of three generations of career aviators. I'm continuing the tradition as a UH60M pilot.”
11.
“My Grandpa 1930’s.”
12.
“My grandad in 1930 with his motorcycle, which still survives in my garage.”
13.
“My grandpa circa 1930s in the US Navy.”
14.
“My grandpa. Guessing late 30s-early 40s. Dude looked like he enjoyed a good time.”
15.
“My Grandpa, 1930s Chicago.”
16.
"My grandpa in his early 20s, mid 40s or early 50s."
17.
“My grandpa’s got game, c. late 1940’s.”
18.
“My Grandpa on his motorcycle. 1940s.”
19.
“My Dad 1940s (Lower Right with the Helmet On).” 
20.
“T-6 Trainer my father flew in WW2 as part of his pilot training.”
21.
“Today is my dad's 97th birthday. This was always my favorite picture of him. (Late 40s).”
22.
“My Dad. I’m guessing taken in the late 40s. He would have been 90 today.”
23.
“My grandpa at age 16 next to his uncle’s car [Late 1940s].”

1.
“My great grandpa in the 1920’s.”
2.
“My Great Grandpa looking fly in the 20s.”
3.
“My grandpa played at speakeasies in the 20s.”
4.
“My Great-Grandpa 1920s.”
5.
“Grandpa was ripped - 1920’s.”
6.
“Great grandpa, going for a bike ride in a three piece suit (1920s).”
7.
"My Dad's late 1920-30's."
8.
“My Grandpa in the 30s looking cooler than I could ever hope to be.”
9.
“My grandfather in the 1930s. An Italian immigrant and worked in the coal mines of western Pennsylvania.”
10.
“My grandfather circa 1930s beginning a line of three generations of career aviators. I'm continuing the tradition as a UH60M pilot.”
11.
“My Grandpa 1930’s.”
12.
“My grandad in 1930 with his motorcycle, which still survives in my garage.”
13.
“My grandpa circa 1930s in the US Navy.”
14.
“My grandpa. Guessing late 30s-early 40s. Dude looked like he enjoyed a good time.”
15.
“My Grandpa, 1930s Chicago.”
16.
"My grandpa in his early 20s, mid 40s or early 50s."
17.
“My grandpa’s got game, c. late 1940’s.”
18.
“My Grandpa on his motorcycle. 1940s.”
19.
“My Dad 1940s (Lower Right with the Helmet On).” 
20.
“T-6 Trainer my father flew in WW2 as part of his pilot training.”
21.
“Today is my dad's 97th birthday. This was always my favorite picture of him. (Late 40s).”
22.
“My Dad. I’m guessing taken in the late 40s. He would have been 90 today.”
23.
“My grandpa at age 16 next to his uncle’s car [Late 1940s].”