I checked out the 200% enlargement and can only conclude that the glans is merely the lowest tip of a pinecone shaped shadow projected by the left pant leg mostly onto the right pant leg.
I find it hard to really tell anything from these scans. It is probably a defect in the photo reproduction.
I should also like to point out that this reprint documents what may be the first meeting of Cecil and SDSAB member (and former moderator of this forum) Jillgat. After years of reading the questions people ask, he seems to have developed the ability to judge people by the weird things they want to know.
Grienspace, I am SO totally with you. Cecil, IMO this whole column is baffling. Sorry. 
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The picture you chose to enlarge, the guy in boxers, has nothing that looks like a penis at all. This is the considered judgement of myself, Bonzo, and The Cat Who Walks Alone. We’ve all spent far too much time this morning, crowded around the computer, trying to spot penises.
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The guy in briefs, contrariwise, does have a definite bulge right where a normal penis bulge would be, hanging to the left (his right).
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However, none of us can see a penis head sticking out of the left side of the briefs, either.
Grienspace’s link is to the column.
Here’s the original Sears picture, http://www.straightdope.com/columns/art/brief1.jpg
Here’s Cecil’s blowup of the boxers.
http://www.straightdope.com/columns/art/brief2.jpg
Here’s Ron’s tiny picture of the brief with an arrow pointing to where the penis supposedly is.
http://www.straightdope.com/columns/art/brief3.jpg
Why am I flashing on the ghost in Three Men and a Baby?
I can’t figure out where people see a penis in either picture. But then, I haven’t spend hours with a magnifying glass poring over black and white scans in the hope of spotting a male member. My mother always warned me that doing so could make you go blind.
There are a couple of U-shaped spots below lower edges of shorts legs that could be glandes, but which are anatomically improbable, and have every indication of being technical faults in the printing.
I’m tellin’ you, I’ve seen the actual catalog and the computer scans don’t do the original justice. There is something there in the original… it does appear to be a glans, but if so, the guy had a mondo organ. I tend to think it was a jokester working on the catalog. I don’t remember seeing the briefs pic. with the telltail tip in the catalog.
Okay, Snopes has a better picture, and they make it clear that it’s supposed to be the head of a penis hanging down from the boxers on the boxer model’s left leg (to the viewer’s right), next to the leg of the unoccupied boxer shorts labeled “6”.
On the Snopes picture you can see something round and blobby that might be the head of a penis, but the big question is–why? Why a penis on page 602 of the Sears catalog? Surely they had proofreaders. 1975 wasn’t the Dark Ages.
Cecil’s blowup of the boxers just shows a big blur there, that doesn’t look like the head of a penis at all to me. Cecil, you need to (a) get a better picture and (b) make it more clear in the column exactly where we’re supposed to look.
Snopes says it’s “undetermined”.
http://www.snopes.com/business/hidden/sears.htm
And for your reading pleasure, if you’re staring down the long dark tunnel of a dreary Thursday afternoon, here’s the Snopes Penis Page. Enjoy! 
And I ran this whole thing past the Better Half when he came home for lunch, and here’s his reaction:
“Put in big caps–GET A LIFE.”
He couldn’t see anything, either, although now that I realize I was having him look in the wrong place, maybe I’ll have him take a look at the boxers when he gets home tonight.
That was some pretty good research DDG. Now if someone could track down the name of the model and interview him, the whole contoversy could be eliminated. Can you imagine having the most discussed penis in the history of mankind?
Does anyone remember the song “The Man on Page 602”?
All I recall is someone singing “I’d send them all my money, to make a wish come true. I just wish I was the man on page 602”
It was recorded by “Zoot Fenster” a/k/a Jack Barlow.
Toby said
Read DDG’s response and the snopes link provided and you can even frickin’ listen to the song!
See, everyone keeps saying this, but I don’t think so. If he were wearing boxers the way most people do nowadays, then yes, but this was a quarter century ago, and the waist of his boxers is actually at his waist. As such, the crotch of the shorts—the actual place where the fabric joins—would be right about at his crotch. And that, in turn, makes it fairly believable that his penis would be poking out the bottoms of the boxers. Maybe he’s a little on the lengthy side, but not outrageously so as is implied by Jill and by Cecil himself.
Eh, sorry, Grienspace, but I rather suspect Bill Clinton’s got that particular title locked up…
It must be my age. Short term memory is going 
It must be my age. Short term memory is going
This may be somewhat off topic, but I’ve heard that there is something extermely weird visible on one of the underwear models in the 2000 J.C. Penney’s Christmas Wish Book. The comment I heard was that “It might be some kind of sexual organ” Does anyone know anything about this?
"Can you imagine having the most discussed penis in the history of mankind?
Eh, sorry, Grienspace, but I rather suspect Bill Clinton’s got that particular title locked up…"
Mr. Dillinger would be turning in his grave. Unless they cut Bill’s off and send it to the Smithsonian. When he’s dead, of course. <What’s that? > Hilliary says now’s OK?
How about Napolean’s? Auctioned off to a urologist at Sotheby’s.
If his penis really was dangling, wouldn’t the person who took the photo notice?
Another explination is that maybe the photo was doctored to add it, and that photo somehow got into the catalog without inspection.
In any case, I really don’t buy Sears’ explination. Sure a random blemish would just happen to be in that exact spot. Right…
Well, I had not heard the “Dillinger’s penis” UL before. Thank you so much for sharing it with me, Sam. :rolleyes:
http://www.snopes.com/sex/penile/dilling.htm
[it’s fascinating, trying to visualize a scenario in which a coroner really would cut off Dillinger’s penis and ship it off to the Smithsonian]