# The Black Loafer



## Patrick06790 (Apr 10, 2005)

A friend of mine was at Brown in the 1950s. At the time the phrase for being cool was "shoe."

Yes, "shoe." And the "shoe" guys wore brown or burgundy penny loafers.

Only the Slide Rule Brigade wore black loafers, according to Val. They might have been genuises, but they were not "shoe."

Val is not one of us, but he has eyes and he notices things. He spotted my black Sebagos one night in a church basement and told me about being shoe at Brown in the 1950s.

Sometimes I wear black loafers and think "Yes, this is cool, this is sleek, this is hard-edged."

At other times the notion of a black loafer seems absurd, or at least a black penny loafer, as opposed to some elegant shell cordovan creation from Alden. Like one of those tux t-shirts - ersatz elegance, egregious gussification of an inherently casual item.

Here I am in some pretty harmless casual togs, with brown and black flat strap penny loafers (brown Sebago Cayman II, black AE Walden).

Does one look hipper than the other, somehow? Would it make a difference to do the comparison in a beef roll configuration?

Is one version shoe?

Or do I just have far too much time on my hands?


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## AldenPyle (Oct 8, 2006)

I've never tried black loafers, but I admit to being black-curious.


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## Naval Gent (May 12, 2007)

Cool and hip are concepts outside my experience, but I did wear black Alden pennies today. With gray tropical worsteds. I probably would not own these except for a fortuitous e-Bay transaction, but I do like them as an alternative to my black tassels in my business-casual workplace. I don't wear black shoes with khakis unless I'm doing my part time government job.

Scott


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## Speas (Mar 11, 2004)

I wear them occasionally. The key to me is the sock (or lack thereof). Black or grey kills it - color makes it.


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## Quay (Mar 29, 2008)

Black weejun-style loafers are what they are. They could indeed, at least these days, be quite shoe. 

The first pic seems more shoe to me while the second works less well but to my jaundiced eye it's just because of the plaid. Colors match, natch, but the black might do better without the blanket reminders. Perhaps stripes?

The fact you changed your belt puts you in the hip category, if not the hip, slick and cool.

My two cents, change not necessary but appreciated.


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## Jovan (Mar 7, 2006)

The black ones don't look as good with your casual outfit, IMO.


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## anselmo1 (Dec 22, 2006)

I wouldn't be caught in "black" penny or beef roll loafers no matter if they were Alden, AE, Cole Haan or Sebago. Cordovan or Brown are the only colors to wear as a penny loafers. Don't get me wrong, I do own black shoes but not in penny or beef roll loafers. One of my favorite's are my AE black Graysons.


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## TMMKC (Aug 2, 2007)

Black loafers just don't look right with khakis and cords, IMO. Too severe.


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## Reddington (Nov 15, 2007)

Shoe









Not Shoe









Full disclosure......I own a pair of black pennies, however, I never seem to be in the right frame of mind to wear them. The brown pennies are just so much more.....'shoe'. :icon_smile_wink:


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## Reds & Tops (Feb 20, 2009)

I own one pair of black shoes - 3 eye bluchers. There's just something about black that I don't like when it comes to dress. 

Of course, that's just my opinion. If my better half had her way I'd wear black all the time. Thankfully, she hasn't tossed the madras and oxford just yet!:icon_smile_wink:


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## closerlook (Sep 3, 2008)

I'm on board with this thread, and with black loafers. 
Sometimes, however, like patrick suggests, i feel like black loafers simply fill the void because one can't wear tassel mocs (like the grayson above) for every occasion. are they a place holder? maybe, but i hope not.
they are for sure, less versatile than the "burgundy."

shop around, but the walden is probably the best bet.


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## windsor (Dec 12, 2006)

Well Patrick, looks like I'm in your company with a pair of black Sabagos. Also have a pair of black EG for Paul Stuart. I see nothing wrong with them. It all depends on what they are paired with. Are burgundy loafers more versatile...yes I think so, so I have those too and in greater numbers. Speaking of bygone expressions, before there was "shoe"(which I never heard in the Midwest) there was "cat". Oh, thats cat, man!


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## Pgolden (May 13, 2006)

*Shoe and black penny memories*

"Shoe" comes from the 1950s bebop musicians. Not just well-dressed, but in the latest fashions. Of course, Miles Davis would qualify and I'm not so sure you wouldn't see him in black Weejuns

My experience with black penny loafers (flat-strap, never beef-rolls) dates to the mid 1960s. We wore them for dress--with blue blazers and gray flannels, and, heaven forgive us, with suits. Of course, I wouldn't recommend this for serious business wear but I'm thinking about giving it a go. Also, quite naturally, once our parents bought shoes to wear for dress, we then wore them with blue jeans. That's another enduring image, and one I like: black penny loafers and sweat socks yellowed by the wash worn with Levi's. Do not ever remember wearing them with khakis.


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## young guy (Jan 6, 2005)

my black bass weejuns are my favorites after my old topsiders, wear them with white wool socks


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## Cowtown (Aug 10, 2006)

I have a pair of black AE Randolphs. Great shoes, although they may not be shoe. 

I love them and will pair them with khakis on occasion. While I agree that cordovan or brown look better, I don't care and wear my black loafers with pride.


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## Jaxson613 (Oct 17, 2008)

I too own a pair of black AE Randolph's in shell. Great shoe! I went back and forth on whether to go black or burgundy. The brown look good in that picture. I guess I need to buy another pair.
How'd you get Jay Leno to pose for those pictures?


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## Brooksfan (Jan 25, 2005)

Patrick-Once you go black you'll never go back. Trust me, they're fine.


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## eagle2250 (Mar 24, 2006)

Patrick: You have the ability to make it all look good but, while I have several pair of black shoes in the collection, I can't see black penny loafers as ever being one of my options. I just don't think they would look right on my feet. However, I do look good in my burgundy, brown and tan penny loafers!


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## Ron_A (Jun 5, 2007)

Naval Gent said:


> Cool and hip are concepts outside my experience, but I did wear black Alden pennies today. With gray tropical worsteds. I probably would not own these except for a fortuitous e-Bay transaction, but I do like them as an alternative to my black tassels in my business-casual workplace. I don't wear black shoes with khakis unless I'm doing my part time government job.
> 
> Scott


+1. IMO, black pennies could look good with gray pants, but not with khakis.


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## hcivic91 (Aug 29, 2006)

I too have a pair of black pennies but mine never make it out the front door. Each time I try them I end up thinking that some shade of brown would better compliment the ensemble. Basically in any circumstance that it seems like a black loafer might work a brown or burgundy works better.


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## Joe Tradly (Jan 21, 2006)

I don't like black pennies with khakis.

I do wear black weejuns with a navy blue poplin suit. Casual suit, casual shoe.

JB


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## Joe Beamish (Mar 21, 2008)

I prefer brown/burgundy loafers with khakis. 

Black loafers could look shoe with white pants (I think), or with any blue pant including jeans.


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## Markus (Sep 14, 2004)

*Black Pennies are cool*

Patrick you're already on the right track. IMHO black pennies go great with khakis.

1) We talk a lot here about brown pennies, but really, good ones are pretty rare, aren't they? I'm talking about a real brown color, not a cordovan that has been polished with brown polish. Brown loafers in genuine shell or smooth finished calf are uncommon. Yes, there are a lot of quasi-penny loafers out there in brown leather, but they're not the kind of flat-strap weejun/alden style I'm talking about. 99% of the loafers I see are "oxblood" or cordovan colored...

2) Yes, cordovan colored loafers "go better" with khaki. That's the whole point of wearing black ones, they're uncommon and cooler looking. I wish i owned a pair!

Keep it going - your look is solid.


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## Patrick06790 (Apr 10, 2005)

*It comes down to this...*

With the brown I am more likely to say "Hiya, have an iced tea?"

With the black I am more likely to say "Just answer the question, champ."


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## Joe Beamish (Mar 21, 2008)

It's all relative. Most men only care about comfort in shoes. Black sneakers are very common now, even with suits in corporate presentations, those club footed things that security guards wear. 

I remember thinking how cool my Intro to Philosophy grad assistant was, way back when. He wore black pennies. So for awhile that's the only shoe I wore. 

They look a bit off to me in these photos, like you think you know what you're doing, but don't.


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## MichaelB (Dec 17, 2004)

*"Shoe"*

Calvin Trillin wrote a book called "Remembering Denny," which is in part a memoir of Trillin's undergraduate days at Yale in the mid-1950's. He devotes a page or two to the term "shoe" as the Yale synonym for "cool." Trillin says that "shoe" was an abbreviation of "white shoe," as in "a white-shoe law firm." In other words, the WASPy, nonchalant, to-the-manner-born types who wore white bucks.


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## 127.72 MHz (Feb 16, 2007)

Patrick06790 said:


> A friend of mine was at Brown in the 1950s. At the time the phrase for being cool was "shoe."
> 
> Yes, "shoe." And the "shoe" guys wore brown or burgundy penny loafers.
> 
> ...


To me there's an important distinction. Your images display what I think of as "The classic black and brown Penny."

I have several pairs of kiltie's ranging from the casual Bass to the more formal AE Grayson's and Alden tassel Moccasin 563. (I want some 664's as well)

I have loafers like the AE Randolph in shell,...

And although they might work with the khakis nothing would be as quintessentially classic as the penny's you're wearing.

Just my two centavos,

Bill Woodward
Portland, Oregon

Very nice images,...


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## 127.72 MHz (Feb 16, 2007)

MichaelB said:


> Calvin Trillin wrote a book called "Remembering Denny," which is in part a memoir of Trillin's undergraduate days at Yale in the mid-1950's. He devotes a page or two to the term "shoe" as the Yale synonym for "cool." Trillin says that "shoe" was an abbreviation of "white shoe," as in "a white-shoe law firm." In other words, the WASPy, nonchalant, to-the-manner-born types who wore white bucks.


I love to read Calvin Trillin. One of my favorite reads was https://books.google.com/books?id=5...rontcover&dq=inauthor:Calvin+inauthor:Trillin

Bill Woodward
Portland, Oregon


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## closerlook (Sep 3, 2008)

*can this be a coincidence?*



Patrick06790 said:


> A friend of mine was at Brown in the 1950s. At the time the phrase for being cool was "shoe."
> 
> Yes, "shoe." And the "shoe" guys wore brown or burgundy penny loafers.
> 
> ...


the issue of "shoe" popped up on the ivy league look blog today!
https://theivyleaguelook.blogspot.com/

edit: indeed, it was not a coincidence, the blog cites this very thread. how meta.


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## mcarthur (Jul 18, 2005)

A-LHS black shell
I like the look


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## cumberlandpeal (May 12, 2006)

I grew up and was educated privately in the south and wore only brown shoes until I was in my late 40s at which point I began to add black to my inventory. As I began to spend more time in foreign capitals I observed that the brown thing was to a large extent an affectation in business wear that was supplying diminishing returns to my self image. I now stick with black with business suits and brown for country and casual wear.

I have black loafers but they are more formal, English, shoes that I use to dress down suits. Black penny or strap loafers with khakis strike me, perhaps vestigially, as very wrong.

Occasionally when traveling in the U.S. I will wear one of my well worn Peal brown captoes with a blue suit and feel young again. Wearing black loafers with khakis would make me feel even older than I am and...more foolish.


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## Pitt 84 (Feb 22, 2009)

*black pennies*

Gentelmen:

It's all perception, depending on your age, locus, upbringing, education, social situation, & when you discovered black pennies...

When I was a young whippersnapper in grade school & jr. hi. the truely cool guys wore black pennies (beef rolls & straps, don't know the make). Couldn't wait until I got my first pair, Mom thought they were sloppy & Dad thought men wore lace shoes - girls wore slip-ons. I remember doing odd jobs to earn the money for a pair of Thom McCann's, was I cool first black pennies & first varsity letter...actually the pinnacle of our socitey. We were totally cool in striped OCBB, chinos, lettersweaters, woven belts & black pennies with white wool gym sox...still brings a grin.

When we moved from Tucson to Pittsburgh the world of a high sophmore was drastically altered no one wore loafers of any color...they were for catholic girls & cheerleaders. I couldn't get behind gunboat wingtips, split toe bluchers, & lesser laced styles that the guys wore (we were in my Dad's world now). I stuck to my guns or loafers and discovered J&M, Cole Hann, Seebago, & Weejuns. Despite my deviant behaviour' I attained cool but won no converts.

As I aged other styles and colors came into play...but if you look for me on Saturday I'll be the older guy dressed in chinos with a woven belt, striped OCBB, lite colored crew sox, black pennies...grinning and feeling inwardly cool...


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## bd79cc (Dec 20, 2006)

Pgolden said:


> That's another enduring image, and one I like: black penny loafers and sweat socks yellowed by the wash worn with Levi's.


I still do this and learned it the same way you did. Thanks for the recollection, PG.

Patrick, I do believe that the coolness of the dark blue and green in your shirt, plus the cool silver of your hair, make the black loafers and belt work. Very shoe!


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## bd79cc (Dec 20, 2006)

P.S. I like to wear 987s (Alden LHS in black cordovan) with olive pants, per mac's deft illustration. :icon_smile:


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## DonV (Apr 2, 2006)

I've been debating black loafers for myself for a while now. I have black bit loafers that I like to wear with gray or charcoal trousers and OCBD and occasionally with a suit. (If the suit is something required for work, though, I don't wear them with the suit).

If I get a pair of cordovan tassel loafers, I'll have to decide between black and #8. The #8 would work with tan and gray odd trousers and I might or might not like it with suits at work. The black would work with gray trousers and navy or charcoal suits; just not with tan trousers.

I kind of want an unlined BB penny loafer too. As I already have the #8 lined version, I'm not sure I'd want another one that is basically the same thing but unlined. I'm not sure what I'd wear the black penny with other than gray trousers, though. I've tried to make my current LHS work with jeans, but I feel like the leg opening is too narrow for such a substantial shoe (I have Levi's 501 currently). Does anyone else have this issue? If I could get the shoe to work with jeans for me, I might try black penny loafers for that. Not sure what else I'd wear as part of this ensemble, though.


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## CactusMark (Feb 14, 2007)

I just can't get behind the idea of black penny loafers. The closest that I can get to liking the idea is the picture of Cary Grant found here where he is wearing tux with the shoes in question; still it just isn't appealing to me. The fact that I like this look at all has everything to do with GTHing a tuxedo rather than liking black pennies.

I think that my basic issue is that black is too formal of a color for the very casual penny loafer. I have, and like, black Alden tassels, the 660, and to me, they are formal enough to pass since I will wear tassels with a suit. However, since I won't wear pennies with a suit, pennies in black is a non-starter.


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## Thom Browne's Schooldays (Jul 29, 2007)

Nice thread.

I go back and forth on it.
I think Black pennies (w/o shoes, or with a light sock) can look great with shorts or light summer pants (black pennies and oxford cloth pants...).

Would also think a more matte finish (probably sans beefroll) would look better, trouble iss most black pennies I see have an unshoe plastic finish to them.

I remember one poster here saying that in his youth, balck weejuns were always considred the proper thing to wear with blazer and flannels.

Didn;t michael jackson's trademark used to be black weejuns, white socks, black jeans?


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## Mazama (May 21, 2009)

*Could this be the genisus of "shoe" slang and leather color bias?*

Hard to remember in an era when Ivies ban military recruiters but before the mid-70s there was a strong connection between Ivy grads and service in the U.S. Navy. So maybe the 1950s Ivy shoe slang and related biases evolved from Navy veterans flooding campuses, even the Ivies, after WWII.

In the 1930s "brown shoe" was a term for naval aviators, the first U.S. Navy officers to wear khaki uniforms (presumably because they traveled better in aircraft of the era). Because of the glamour, panache and exclusivity supposedly associated with aviators, "brown shoes" adopted the term as a badge of honor for themselves and an indication of their own sense of superiority to other naval personnel.

Even when non-aviator officers and CPOs started wearing khakis during WWII they still wore black shoes with them. So "black shoe Navy", a derisive term if spoken by an aviator, referred to everyone and everything not associated with naval aviation.

Sometime after WWII all officers and CPOs started wearing brown shoes with khaki uniforms, and the term "brown shoe", though still in use, lost a lot of its original meaning.

In the 1960s there were no standard issue brown shoes so the shoes worn by officers and CPOs were far from uniform, which stood out glaringly when everyone lined up for inspections or ceremonies. For guidance the acceptable shade of leather was referred to as baby sh-t brown.

And enlisted personnel in that era - at least outside aviation units - were known as "black shoes" since that's the only color shoe they wore.

U.S. Navy officers have always worn white shoes with white uniforms in all modern eras, of course, which set them apart from both enlisted personnel and the officers of the other service branches.


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## Pgolden (May 13, 2006)

MichaelB said:


> Calvin Trillin wrote a book called "Remembering Denny," which is in part a memoir of Trillin's undergraduate days at Yale in the mid-1950's. He devotes a page or two to the term "shoe" as the Yale synonym for "cool." Trillin says that "shoe" was an abbreviation of "white shoe," as in "a white-shoe law firm." In other words, the WASPy, nonchalant, to-the-manner-born types who wore white bucks.


"Shoe," according to the Dictionary of American Slang, was an expression that originated with the bebop crowd. Sounds more likely than with the Ivy Leaguers.


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## jacflash (Aug 29, 2008)

I never heard "shoe" used in that way before, but... when I was at Cornell in the '80s, at least in my (very well-dressed along trad lines) fraternity, black Weejuns -- ideally a bit battered, of course -- were Very Much The Thing, particularly among our house's sizable Phillips Academy contingent. (And tasseled loafers were very very much NOT the thing, FWIW.) 

I still own a pair of black loafers -- in fact, I was admiring a pair of black shell LHSs recently, and might go get some for myself -- and I still can't wear tassels without feeling like an idiot. Funny how these things stay with us.


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## Green Lantern (Dec 19, 2006)

*Black Pennies work with*

Stone colored Bill's khakis, White crew neck tee shirt with black V-Neck sweater.


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