Dickies

Playboy Sept. 1066

Broomsticks and Beatles Lookalikes

Playboy Sept. 1966

Seven Seas and Austin Hill

Playboy Sept. 1966

Heh heh heh... shiver her timbers...

YMM Jaymar Slacks

Playboy Sept. 1966

Fortrel Mr. Hicks

Playboy Sept. 1966

h.i.s Nonconformity

Playboy Sept. 1966

h.i.s was apparently way before of it's time.  Wearing nice clothes as a statement against mainstream nonconformity.  "I've been wearing slacks after it was cool, man..."

Levi's on a Motorcycle

Playboy Oct. 1968

Groovlee!

Oct. 1968

Jaymar Slacks

Playboy Sept. 1964

Levi's Jeans

Playboy Nov. 1964

Riegel Pants

Playboy Sept. 1964

h.i.s for Classics Majors

Playboy Sept. 1964

The Saga of Brick Mason

Playboy Sept. 1966

     I really recommend that you give this one a read-though.  It's a story of one Brick Mason who eats healthy breakfasts and dances Go-Go.  He dates three girls in a single day (one of whom is named "Yes Yes"), and drops some wisdom regarding the economy.

     Why don't they make ads like this anymore?

Scrubdenims

Playboy Sept. 1966

White Horse Scotch

Playboy Nov. 1967

     Most of the ads I see that feature/include/show women do so in a less-than-flattering manner.  Probably due to the target audience of a Playboy magazine, but most of the time women are shown as being subservient and/or objectified creatures best suited to cater to man's pleasures, which of course makes such advertisements good targets for us modern-day readers to scoff and snort derisively at.  So I find this ad refreshing, as it features a jaunty pants-wearing woman who evidently plays and works just like the boys do.
     And let us not forget the awesome plaid/turtleneck/orange glasses combo.  Retch.

More Denim, from Graniteville

Playboy Sept. 1966

Apparently, London is sideways, likes Coca-Cola and Skol, flies Air India, and wears denim.  Eh, close enough to America, I guess.

Dickies Slacks

Playboy Sept. 1964

Is a "campus tiger" an escaped zoo animal, or a sexual predator? 

Because I'm kinda getting both from this ad.

Broomsticks Slacks

Playboy Sept. 1964

     OH NO!  That woman is kneeling on that tiny man's shoulder!  Really though, you'd think they could have tried a little harder to edit the man into a more believable position, instead of obviously in the foreground of this picture.   Regardless, I thought this was an interesting ad since it appears to be advertising both the pants and the Mustang.