All posts tagged Penny Loafers

Loafers by Billax

Loafer rack full of shoes

This post is a reprinting of a post on AAAC’s Trad Forum by Billax. Billax is not only one of my style role models, but a friend and a man that was Trad back when it was called Ivy League.

The loafer is a slip-on shoe created from a soled and heeled Moccasin. It is a sub-set of slip-on shoes. Web searches show Spaulding to be the first producer in the USA of such a shoe, c. 1933. The MUCH more famous Bass Weejun didn’t show up until 4 years later – when G.H. Bass introduced the flat-strap penny loafer in 1937. The “Weejun” name is a corruption of Norwegian, in reference to the country of origin of the the original loafer. The term loafer, so Internet experts propose, comes from the “loafing sheds” on farms adjacent to their cattle barns. Apparently, Esquire Magazine spotted these slipper-like shoes on the feet of farmers working around the barns and loafing sheds of Norway and brought them to the attention of their then-vast readership. The link between Norwegian farmers, loafing sheds, Esquire, and slippers is, apparently, lost in the mists of time. Just as an aside, 1937 was a landmark year for iconic traditional apparel. Not only the year of the Weejun introduction, but also the year in which Baracuta introduced their G9 jacket. If you have both Weejuns and a G9, you’re pretty much approaching icon status yourself!

How does any of this relate to me? Well, from my escape from the womb in 1942 until late in High School, my Mom bought my shoes at Sears. Most folks today have no idea how dominant Sears was as a retailer in the late 40s through the 50s. There were very few specialty stores – of any kind – though we’d walk right past a Thom McAn shoe store on the way to buy shoes at Sears. How amazing Thom McAn was to me – a store that sold only shoes! Oh, Man, did I ever want to go inside! But, Sear’s it was. My Mom or Dad, though mostly my Mom, would ask the Sear’s shoe salesman to fit me with a pair of Oxfords,
Old Oxford Shoes
“with room to grow.” Out came the Brannock device.

After the measurement, the shoe guy brought out a pair of Oxfords – his choice of model as I recall – and put them on my dawgs. Then it was off to the fluoroscope.

FluoroscopebestI stood on the machine, put my feet into the slot, and the salesman, my Mom, and I all peered into our portals. The shoe guy would say, “Wiggle your toes,” and we’d all see a real-time, moving Xray of my feet within a vague outline of the shoe. The salesman would say, “Plenty of room to grow, Ma’am,” and my Mom would say, “We’ll take them.” That was the shoe buying experience for me until my Junior year in High School, when I no longer needed “room to grow” for my shoes.
Fluoroscopefootimage In the summer after my Junior year in High School, I asked the folks for a little cash to buy some Keds. Fifty cents a week for allowance wasn’t enough to allow me much autonomy. My Dad spoke up for me and gave me money enough to buy a pair of Keds. But a few months later, the college cousins came to my house for Thanksgiving, wearing identical Bass Weejuns. I was thunderstruck! They were the most beautiful shoes I had ever seen. Heck, other than ’57 Chevys, they were the most beautiful “things” I had ever seen.
1957-chevrolet The flat strap, the moccasin construction, the permanent sheen of the Brush-off leather – they were over the top to me. My Uncle Jack, Dad to the Northwestern cousin, saw me staring and studying. Although it’s a story for a different time, my Uncle Jack was a VERY sharp dresser. To close this sidebar, in the late 50’s he wore Florsheim Imperial Longwings, 3/2 Tweed sport coats, Amber-colored Peccary gloves (though I only came to know the word peccary a couple of years ago), and the most dramatic Black and White, Raglan sleeved, Wool Herringbone Top coat I have EVER seen.

But back on topic, my Uncle had a short, private, conversation with my Dad. After the guests had left, my Dad said he’d noticed my interest in the cousins’ shoes. He went on to say that, “I like those shoes myself, Son, so go get yourself a pair for college.” It was still ten months until I would enroll in college, but I’d been given the green light! They didn’t have Weejuns at Sears, or at Thom McAn, but I finally found them at a Department store. No fluoroscope machine was employed, but the “shoe guy” found me a great pair. I kept them – unused – in their box until the day I arrived at college.
flatstrap Weejun LOGAN I have had at least one pair of Weejun’s in my closet ever since. Life has mostly been good to me, and over the years, I’ve ended up with several pairs of loafers – in Shell Cordovan, in Sharkskin, and other exotica. But the shoes that most often have their trees removed are Weejuns.
Loafer Rack Full of ShoesDuring my college years, I wasn’t that sensible. Heck, I’m not that sensible now. I bought things that I didn’t need or even particularly like. I bought Hanover Venetian loafers and I never bought another pair of Venetians.

Vintage Hanover Venetians

  and I bought Bass tassel loafers, but didn’t wear them much
Bass Tassel Loafers  But I always kept going back to the Weejuns. I still do.  All loafers are not created equal!

  I find nothing wrong with Sebago Caymans and Sebago beefrolls.

Picture of Sebago beef Roll loafersHad my cousins’ worn those, I would have bought, and been loyal to, that brand. Of course, in the 50’s and 60’s nearly every shoe manufacturer made and sold flat strap Penny loafers. But the first ones I knew about and the ones with that evocative name, stayed my choice. I was – and I remain – a Weejuns guy.

Accessories Part 1: Socks


As I have mentioned here before, I wear a blue OCBD  (oxford cloth button down) shirt and khaki chinos almost every day. While I love the simplicity of my dress code, it does not produce the most exciting outfits. Also, I work in a casual office and do not get to utilize a tie or jacket. After a while I started to look for other ways to add some color to my “uniform.” Since then I have learned that socks are a simple way to add color, patterns, and even texture to my otherwise drab outfits.

Here are a few examples of argyle socks.





There are a lot options when it comes to socks. They come in almost any color and pattern. I am an advocate for argyle, rugby stripe, regimental, and fair isle socks (in the winter). My only other recommendation is that you get over-calf-socks (OTC). I am not a fan of constantly having to pull my socks up and I think that OTC socks offer a better fit..

Another reason why socks are such good accessories is that they are affordable. You can spend $30-40 and get a really nice pair of wool socks. However, you can also go to Target and get a cool pair of socks for $5.  Most of the socks featured in this post came from The Gap, Target, J.Crew, and maybe Kohls. This fits in nicely with my motto of “affordability and availability.”

Examples of striped socks.






Not striped, but I like these and wanted to include them.


Another article of clothing made by my talented sister. I usually wear these with slippers. They are warm and cozy.



Handmade-Socks-ShoesI do need  a pair of red socks. I like the way they look with brown suede

Socks are a great accessory. In this post, I only used a few pair of shoes and the same pair of chinos to provide some examples. I could have made even more interesting color combinations by mixing in different pants and shoes. So, start thinking about mixing suede shoes, corduroy pants, and wool socks or navy chinos, red socks, and brown shoes. I have found that by experimenting with different sock, shoe, and pant combos that I can make what were very similar outfits look pretty different. After you get done reading this post, take a trip to your sock drawer, take stock, and start working up few outfits. If you are anywhere near as boring as I am you may find that socks can help you mix it up.

The Penny Loafer and Bass Weejuns

Penny Loafer

As far as traditional footwear goes there are a lot of options out there. You can wear wingtips, plain toe bluchers, saddle shoes, bucks, moccasins and the list goes on (almost anything that does not have a square toe). However, there is no other footwear that is as quintessentially American as the penny loafer. Like most things quintessentially American it has roots somewhere else.The loafer was not invented in America, but rather in Norway. It was a casual shoe worn by dairy farmers and made by off-season fisherman. The shoe was introduced in America after World War I by the Spaulding company and popularized by Esquire Magazine.

Burgundy Bass WeejunBurgundy Bass Weejun Penny Loafer

Vintage Bass Ad 19651965 Bass Weejun Ad (from

Bass started producing their version of the loafer in 1936. Their loafer was a little different. It had an extra strip of leather across the top and a diamond cutout. It was called the Weejun. One can presume this name borrows from the word Norwegian as the penny loafer was borrowed from the culture of Norway. The loafer started out as a casual shoe and worked its way into more formal settings. It was a staple on college campuses in the 1950’s and is synonymous with Ivy League style. In fact, it was students who started the practice of placing pennies in the diamond cutout and in doing so helped create the term “penny” loafer.  The penny loafer can now be worn in a variety of settings without causing a stir. Whether you are in denim with a flannel shirt or a blazer with wool trousers, penny loafers will look appropriate.

Brown WeejunsBrown Bass Weejun Penny Loafer

1960 Bass Ad1960 Bass Weejun Ad (from

Currently, there are many companies that manufacture a very nice penny loafer. I myself am a fan of  the Weejun. There is a Bass outlet not far from my home. I can purchase a pair there for somewhere between $50-$70. This is a nice markdown if you consider that the average retail price is around $100. The fact that they are affordable, available and classic are the reasons that lead me to continue to purchase Bass Weejuns. They also fit me. This last attribute cannot be overlooked. I have tried to make many pairs of shoes fit, that just will not. Due to my stubbornness, and my desire for these shoes my feet have suffered through many days, but not anymore.

Brown Bass Weejun and Agryle SockDay off fun. Casual cuff and argyle socks

1963 Bass Weejun Ad1963 Bass Weejun Ad (from