When Cadillac Ruled The Road: A Gallery Of ’50s & ’60s Elegance

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– Posted on August 22, 2025

Text by Patrick Bell.

The Cadillac Automobile Company was formed on this day in 1902.  Their first car was produced a couple of months later as a 1903 model.  They were purchased by General Motors in 1909, and by that time were an established premier luxury car manufacturer.  That mission has remained the same over the past 123 years, although it hasn’t always been achieved.

Today we have a selection of images from what many consider their best years, so let’s get started.

Our first shot was a ’64 model that appears to be Series 62 Coupe or Coupe deVille, and it was from New Hampshire.  The license plate date could be ’65 or ’67, and is unique as there is no county designation which consisted of a two letter code before the number.  That leads me to think this may have been a government official’s car, perhaps a judge.  The setting had a Florida vibe, and the white over black ’58 Mercury in the far left background had a license plate that looks blue with white lettering; Florida’s colors for ’66-’67.  Also back there, a black ’63 Oldsmobile F-85 Jetfire, and a yellow ’65 or ’66 Ford Mustang convertible.  The lady and the boy don’t look related due to the opposite hair colors, but stranger things have happened. Another odd thing to me; an electrical plug on the light pole that is so close to the pool.

Parked in front of a music store was a ’53 Coupe de Ville, all nice and clean.  It had a California license plate, and that could have been the location as well.  The de Ville carried a $424 price premium over the Series Sixty-Two Coupe ($3995 vs. $3571), and for the third year in a row was the best seller of the two.

A ’55 Series 62 convertible with a same year Michigan license plate.  The setting was a parking lot on a cool day, but I am not sure of the building’s purpose; there was a bus parked close to it.  To the left was a ’54 Buick, and on the right edge a light green ’55 Chevrolet Two-Ten 2 door sedan. Parked behind it was a maroon ’46 or ’47 Packard.

Now we are in a rural area on a sunny, summer day where a ’50 Series Sixty-Two sedan was parked by the road.  It was clean and shiny and looked good with the red interior and whitewall tires.  In the driveway across the road was a ’53 Plymouth.

Stepping out of the ’50s for a moment, a lady with a ’48 Series 62 convertible that looked new or at least close to it.  It was parked alongside a blooming bush and perhaps a light pole.  This was the last year of the L head V8 engine, and it carried a base list price of $3442.  It sure looked good in that shade of blue.

This looks like some traveling folks that stopped along the road for a photo opp.  Their ’56 Series Sixty-Two Sedan de Ville with factory air conditioning looked like it was carrying a load, and had a crease in the rear door and fender skirt.  This was the first year for Cadillac’s four door hardtop and it was well received becoming the best selling model for the year.  The man appeared to be using a movie camera, so perhaps he was a professional photographer.

Another ’56 model, this one a Series Sixty-Two coupe with a California license plate used from ’56-’62.  A new 365 cubic inch V8 was standard in the ’56 model year, the first increase since the overhead valve 331 cubic inch was introduced in ’49.

Here was a ’58 Series Sixty-Two Sedan or Sedan de Ville in another beautiful shade of blue.  As far as I know the only difference between the two models was the interior.  This one looked close to new and had a license plate that looks like a Pennsylvania issue except for their distinctive yellow border. Perhaps this one had a license frame that was not visible, or perhaps I am way off.  The building is not a style I am familiar with, as it appears to be apartments above garages.

1959 marked the height of the fin craze (figuratively and literally), and Cadillac certainly played their part.  It was also the year the 390 cubic inch engine came out, and the de Ville graduated to its own series as it had been a part of the Sixty-Two series since its introduction in ’49.  This Coupe de Ville was a color I don’t recall ever seeing, but it looked good if you like yellow.  The two passengers in the back seat looked like they were ready to go and were waiting on the driver.  The car on the right edge may have been a ’55 Buick.

And now we have a couple of young executive types posing by a ’65 Hardtop Sedan de Ville from New Jersey.  The standard engine was the 429 cubic inch version that was introduced the previous year in ’64.  It was parked behind a motorhome, and across the street in the driveway was a Volkswagen Karmann Ghia.  The neighborhood was well established and manicured.

The displacement race marched on with a new 472 cubic inch V8 standard on ’68 models like this Fleetwood Brougham, also from New Jersey.  This was the most expensive non-limousine model for the year with a base list price of $6899.  The neighborhood looked similar to the previous image, and there was a ’61-’67 Ford Econoline in the driveway across the street.

We shall close out with the last year of the decade, a ’69 model that could have been either a Calais or Hardtop Sedan de Ville, but the odds go with the de Ville since over 10 times as many of them sold over the Calais.  It had a ’69 Illinois dealer license plate, and perhaps the gentleman was the dealer. They were out on a narrow dirt road, maybe checking out some property.

Thanks for joining us and have a great day!

 

More Vintage Photos Here