“I’m with stupid” is a saying that has been printed on many T-shirts and posters, usually with an arrow or finger pointing to the “stupid” person. “I’m with stupid” has been cited in print since at least August 1975, when the T-shirts were sold at the Iowa State Fair.
   
The arrow of the 2016 Hillary Clinton presidential campaign logo reminded some of the “I’m with stupid” shirts.
 
 
Wikipedia: I’m with Stupid
I’m with Stupid is a jovial insult, best known as a popular slogan for novelty T-shirts. It may also refer to:
 
. I’m with Stupid (TV series)
. I’m with Stupid (album), by Aimee Mann
. “I’m with Stupid” (Pet Shop Boys song)
. “I’m with Stupid” (Static-X song)
. I’m with Stupid, a book co-written by Gina Barreca and Gene Weingarten
. “I’m with Stupid” (SpongeBob SquarePants)
     
23 August 1975, Ames (IA)

, “From my point of view” by Rod RIggs (editor), pg. 8, col. 5:
(At the Iowa State Fair.—ed.)
There were a lot of t-shirts with various mottos and slogans, including some obviously of original conception. My favorites were a fist with a finger pointing to the wearer’s right and the explanation, “I’m with stupid,” and another with the question, “When the meek inherit the earth, what happens to us tigers?”
 
19 October 1975, The World (Oak Park, IL), “She’ll make a shirt that will fit to a ‘T’” by Jean Guarino, pg. 8, col. 1:
“I’m with stupid” with a finger pointing to the wearer’s right, and “Trust Me” under the picture of a monster are two currently hot items.
 
7 August 1976, New Music Express, ‘Teazers,” pg. 43, col. 2:
... Eric Clapton’s “I’m With Stupid Clapton” T-shirt was a gift from Ronnie (Wood—ed.).
 
27 September 1976, Chicago (IL) Tribune, “T-shirts to order,” Tempo (sec. 2), pg. 1, col. 5:
In the transfer business ,the most popular designs are Starsky & Hutch, the everpresent Fonzie, and a design that has a finger pointing to the side of the wearer with the legend “I’m with Stupid.”
   
OCLC WorldCat record
I’m with stupid
Author: Aimee Mann
Publisher: Los Angeles : Geffen ; [Universal City, Calif.] : Manufactured and distributed by Uni, 1996.
Edition/Format:   Music CD : CD audio : Rock music : English
 
OCLC WorldCat record
I’m with stupid : one man, one woman : 10,000 years of misunderstanding between the sexes cleared right up
Author: Gene Weingarten; Regina Barreca
Publisher: New York : Simon & Schuster, ©2004.
Edition/Format:   Print book : EnglishView all editions and formats
Database: WorldCat
Summary:
The first significant book about men and women actually written by a man and a woman, I’m With Stupid is privy to the dark secrets of both sexes. It’s not a lecture, but an extended argument, a combustion of viewpoints that winds up unearthing startling truths. In the words of Gene and Gina: “Our Mars and Venus breach their orbits and collide in a screaming fireball from Hell.”
 
Snopes
14 July 2015
Glare Shirt
An altered photograph appeared to show Hillary Clinton standing alongside a woman wearing an “I’m with stupid” shirt.
Kim LaCapria
FACT CHECK:  Does a photograph depict an unwitting Hillary Clinton posing next to a woman wearing an “I’m with stupid” shirt?
FASLE