In 1965 Ricky #1090 was introduced as Skipper's friend.
He was sold till 1967 (1965 in the tan skin tone, starting 1966 in the pink skin tone).
Ricky had the same body (and markings) as the same years' SL Skipper dolls and Skooter: © 1963 Mattel, Inc.
He came in a box stating "Skipper's friend Ricky by Mattel" and was dressed in blue shorts, a striped jacket and red cork sandals. He had his own "Ricky" wrist tag. Included in the box were a black metal stand, liner, and booklet.
There were no gift sets with Ricky.
Both sides of Ricky's box:
Ricky is wearing his original striped jacket with pants, socks and shoes from the outfit #1505 "Skateboard Set" from 1965 - 67. Blonde Skipper dressed in "Knit Bit", titian Skipper dressed in the top of the set ("Fun Time") /"Skipper on Wheels" #1032 from 1965. The roller skates come with that set. The jeans skirts' origin is unknown.
Ricky and his "Skateboard Set" #1505 from 1965 - 1967. There's another variation of this shirt with fabric from #1503 "Sunday Suit"
Ricky in #1501 "Lights Out" from 1965 - 1967. Not pictured is the pajama top and the terrycloth scuffs which match the color of the robe. The robe was produced in a light blue and a darker blue.
Left picture: Pink skin Ricky dressed in #1503 "Sunday Suit" from 1965 - 1967 and a tan skin Ricky wearing the pajamas from #1501 "Lights Out", also from 1965 - 1967.
Right picture: Ricky in #1504 "Little Leaguer" from 1965 - 1967.
Wonderful example of a pink skin Ricky doll dressed in #1506 "Let's Explore!" from 1965 - 1967. There's another variation of the shirt with the fabric from Ken's #1409 "Going Huntin'":
Skipper in Ricky's fashion #1502 "Saturday Show" (1965 - 1967) and Ricky in the same fashion (red socks not pictured):