First appears in Glitter and Gold and again in:

The Talent Search Part 1, Scandal, One Jem Too Many, The Bands Break Up, Father's Day, Danse Time, Britrock, Out of the Past, The Day the Music Died.

As far as I know, you don't see the hoodie or guitar on the cartoon.  The shoes (at least in the Glitter N' Gold episode, maybe not later?) are not pink as they are with the produced fashion.

The Talent Search Part 1, One Jem Too Many, Danse Time, Trick or Techrat, The Stingers Hit Town Part 1, The Day the Music Died.

Oddly enough this is a flipside fashion, worn by Aja, not Jem.

Father's Day, The Presidential Dilemma, Hollywood Jem Part 1, Hollywood Jem Part 2.

Trick or Techrat, Out of the Past, Change of Heart, A Father Should Be....

Hollywood Jem Part 2, The Day the Music Died.

Sometimes shown with pink pearl earrings.

The Fan, Alone Again, Out of the Past, Hollywood Jem Part 1, The Stingers Hit Town Part 2, Change of Heart, A Father Should Be....

Thanks to Cosmic Falcon for donating this drawing to the wardrobe section!

Father's Day, Roxy Rumbles, Video Wars, Beauty and the Rock Promoter, Midsummer Night's Madness, The Day the Music Died, That Old Houdini Magic, Riot's Hope, Change of Heart. 

Roxy Rumbles, Renaissance Woman, Straight From the Heart.

Video Wars (reused footage).

That Old Houdini Magic.

The Jem Model sheet number for this fashion is A-68-35.  It was designed for this episode.

Straight From the Heart.

This may have originated as a Kimber fashion; this same design was also used for Shana, and Raya.