Barefoot Pilgrim

A “barefoot pilgrim” was, originally, an unsophisticated car buyer—someone who buys a car at the advertised sticker price and pays too much. This meaning of “barefoot pilgrim” has been cited in print from 1967.
 
A “barefoot pilgrim” in Wall Street slang is an unsophisticated investor—especially, one who invests and loses a lot of money. This meaning of “barefoot pilgrim” has been cited in print since at least 1988.
 
   
Investor Words
barefoot pilgrim
An investor who has lost all money invested in the stock market because of a lack of sophistication and knowledge of trading. “Barefoot” refers to losing ones shoes, and possibly the shirt on one’s back, due to poor investment choices.
 
Investopedia
What Does Barefoot Pilgrim Mean?
Slang for an unsophisticated investor who loses all of his or her wealth by trading equities in the stock market
 
(Historical Dictionary of American Slang)
barefoot pilgrim n. (see quot.)
1980 American Speech (WInter) 310: Car salesmen in north Georgia employ [an intriguing] term…a gullible or uninformed customer is a barefoot pilgrim.
 
Google Books
The Concise New Partridge Dictionary of Slang and Unconventional English
By Eric Partridge, Tom Dalzell and Terry Victor
New York, NY: Routledge
2007
Pg. 33:
barefoot pilgrim noun
in the used car business, a naive, trusting, unsophisticated customer. US 1968
   
Google Books
Get the most for your money when you buy a car
By Valerie Moolman
New York, NY: Cornerstone Library
1967
Pg. 146:
If you bought a car before, were you a “barefoot pilgrim” or a “mooch”?
   
Google Books
The Time-Life Book of Family Finance
By Carlton Smith and Richard Putnam Pratt
New York, NY: Time-Life Books
1970, ©1969
Pg. 86:
The rare person who pays the sticker price for a car is known as a “barefoot pilgrim” in the jargon of the trade, and he is an unfrugal fellow indeed.
   
New York (NY) Times
GUIDES FOR THE BAREFOOT INVESTOR
By ANDREW FEINBERG; Andrew Feinberg is the money columnist for 7 Days, a New York magazine.
Published: July 24, 1988
HIGH STEPPERS, FALLEN ANGELS, AND LOLLIPOPS Wall Street Slang. By Kathleen Odean. 212 pp. New York: Dodd, Mead & Company. $17.95. ABZs OF MONEY & FINANCE By Susan Lee. 219 pp. New York: Poseidon Press. $16.95.
 
For years I assumed that I, a small investor, represented what Wall Street condescendingly called ‘‘the little guy.’’ According to ‘‘High Steppers, Fallen Angels, and Lollipops,’’ however, I flattered myself. Apparently, many Wall Streeters would prefer to think of me as a ‘‘barefoot pilgrim,’’ just another wide-eyed innocent who is supposed to enter the world of investing with fervent hopes and then lose his shirt - and his shoes.
 
Google Books
High Steppers, Fallen Angels, and Lollipops:
Wall Street slang
By Kathleen Odean
New York, NY: Dodd, Mead
1988
Pg. 51:
A mid-century synonym for lamb was lily, indicating a “high-brow” sucker; a more recent synonym is the picturesque barefoot pilgrim, who has lost his shoes as well as his shirt.