The Penny Loafer - casual or dressy?

It is a casual shoe or a dress shoe? The penny loafer is an enigma, so hard to pin down.

And its unusual story is all tied up with that question.

We'll look at the roots of this classic shoe, how it has developed, and talk to style influencers to get their viewpoint. And of course we had to find out what was the best colour.

Penny Loafer Collection

So should you wear them casual style when you're relaxing, or for work or some special occasion?

With its lace up cousins - an oxford, brogue or derby you immediately know that the look is formal, dressy and smart. Definitely dress shoes. But with a penny loafer?  One minute you could see someone wearing them with shorts strolling down the beach, the next bossing the boardroom.

It depends on so many factors - the colour, the material, the style and design, and which country in the world you live in. Sometimes it fits right in, it's conservative and smart, other times it says, 'I'm stylish, an individual, and I'm doing my own thing'.

So let's look at how this slip on classic got started, how it evolved, then look at the best ways to style it and see what may be the best colour choice for you.

The circular history of the penny loafer

The story goes that travelers from the USA visiting Europe in the 1930s learned about and started to like these new moccasin type shoes that were being made in Norway. They had become a big hit in Europe. They had been developed by Norwegian shoe maker Nils Tveranger. Magazines of the time including Esquire showed local farmers and fishermen wearing them. Nils had himself in turn been inspired by the moccasins that native American Indians wore when he had learned to make shoes in the US. So the idea had come full circle.

The word got back and began to spread in the US. Soon a new shoe called 'The Loafer' was developed and launched by the Spaulding family in New Hampshire. Other people also started to manufacture these new shoes and in 1934 boot maker GH Bass of Maine brought out their 'Weejuns' loafer design. (Yes that sounds a bit like Norwegian doesn't it?)  In their design they had added the distinctive leather cross strap with the crescent cut out, and the penny loafer look was born.

Penny loafers being made in a factory in Italy
Photo: Penny Loafers being made in Thomas Bird factory in Italy

We say look because the 'penny' part came later.  Again legend has it that preppy Ivy League students wearing their loafers put a penny in each slot. Well this proved very handy when you'd run out of money after an all nighter and then remembered where you had left two pennies to make that emergency call to get a ride home.  As the years went by and telephone charges went up, the pennys became dimes.

Is this true? An urban myth or maybe just a nice attempt at individual decoration by students with too much time on their hands? Who knows. Anyway the new name had stuck.

So what's with all this history?

Well these smart Ivy Leaguers were soon leaving university and moving up and into the boardrooms of some major US companies, and their penny loafers came with them. Which is why today across the US, from New York to Los Angeles, certain designs of black loafers are now considered as formal as an oxford. And maybe a little more all American too.

Black penny loafer

Evolution of the penny loafer design

Many designers around the world then had their take on adapting and evolving the design. Like trying different toe shapes and adding details to the shoes. Guccio Gucci had worked in the Savoy hotel in London and seen how the post first world war elite loved their horses and racing. The Gucci loafer with its horse-bit, equestrian style metal buckle caused a huge splash when it was launched in the mid 1950s. They also later released their version of the Gucci penny loafer. Loved first by the horse loving European aristocracy, then by Hollywood A listers like Cary Grant and Grace Kelly. These fashionable new loafer shoes showed that a slip on shoe could be elegant, sophisticated and stylish.

And so the stylish Italian style loafer was born.

The smart, elegant Italian look and Italian dress shoes became a huge influence around the 1950s to 1960s and is still with us today.

Another popular loafer design is the tassel loafer, seen below on the left alongside a penny loafer.

Tassel loafer and penny loafer

James Bond wears loafers?

Fans of the original books in the 1950s by author Ian Fleming will know that James Bond preferred his "black casual shoes (he abhorred shoe-laces)." Sounds like loafers to us. You can just see him impeccably groomed and styled wearing a pair of black loafers as he sips his dry martini on the balcony. And when the inevitable long embrace and lingering kiss comes later in the evening, it's so much easier to kick off your loafers than losing your cool while trying to untie your oxford lace ups. Just try it.

Loafer colours - so which one is best for you?

So far we have had a reference to US boardroom executives, and secret agent 007, both wearing their black loafers. Yes, black is the most sensible and versatile colour in any shoe, and the penny loafer is no exception.

This black penny loafer is smart and yet still slightly relaxed. That's not easy to pull off. (Have you ever seen a relaxed cap-toe oxford.) They work with a suit and you can even wear them with jeans, linen or chinos. So if you need one colour to handle most situations, black may be your best option.

Black penny loafers with socks


But if you fancy more than one pair, or are just not excited by black, what are your other choices?

We have found that oxblood is a strong favourite in certain countries. It's deep, rich red/blue tones set of any outfit and adds that splash of colour and interest. Oxblood loafers look particulary good with a blue, navy or neutral suit.

Here you can see them being worn by Ed Ruiz aka @mydapperself. Ed is wearing Thomas Bird oxblood Hampton loafers, sockless with suit trousers and an open neck shirt.  We think it's a great look.


Oxblood loafers with a suit

We asked Ed, "What do you like about loafers and how do you best like to style them?"

Ed: "What makes loafers special to me is how versatile they can be. You can dress them up or dress them down, while simultaneously they can also dress up or dress down an outfit. Versatility is the name of the game with loafers. Some wear their loafers strictly with no-shock socks, some others prefer wearing socks. I actually enjoy styling them both ways, there is a time and a place for each of these two styles and both can be equally attractive."

Here's another photo of Ed wearing them. 

Oxblood loafers with suit trousers

Brown or tan loafers (shown below) are also good choices on the other hand if you don't need to go quite so formal as black but want another versatile colour. The lighter shades of brown are usually seen as less formal and more casual than darker browns.

Brown, tan and chestnut loafers

We have also found blue penny loafers (below) to be increasingly popular with some uber cool guys. OK not maybe in the boardroom (unless you own the company) but in the right situations blue is stunning and individual.

Blue penny loafers with light grey suit

 Finally the so relaxed suede penny loafer.

This must be the most laid back and relaxed of the bunch  Firstly because it's soft suede, not leather, and secondly because it's often a shade of brown. Dressed down with chinos, linen, or blue jeans it really looks the part.

Suede loafers look great with shorts too.  In the photo below, Benn Bromley aka @dailytouchofclass wears Thomas Bird Hampton brown suede loafers with a blue tone open necked shirt and white shorts. Awesome or what?

Brown suede penny loafers worn casual with shorts

We asked Benn, "What's your take on styling them?".

Benn: "Penny Loafers are simply the best blend between casual and classic style. They offer great versatility and can be worn in almost all scenarios. A favourite look of mine is to style a penny loafer with shorts and button up oxford shirt, very nice for summer. Otherwise, I like to wear penny loafers with a suit to work as well."

And here's another photo of Benn wearing them in more detail.

Brown suede penny loafers sockless

So, socks or sock-less?

More and more guys are wearing their loafers without socks as seen with both Ed and Benn above. Sock-less is a good. modern and fresh  look. You could also  use invisible socks to get this look.  A tan helps too. Of course if you are wearing them for work in a more formal environment, socks may be the way to go.

Thomas Bird loafers

We always lean towards designs that follow elegant, European lines.  Our Hampton penny loafer follows this tradition, with an elegant, sweeping profile and slightly longer chiselled toe. We also went for a slightly bolder brushwork style of patina on these shoes, with each pair individual and giving a real hand crafted look.

Our loafers are all made in Italy, to the highest standards, using high grade, full grain calf leather. We incorporate added details like leather linings, stacked leather heels and blake stitched soles.

We currently offer five colours - black, brown, chestnut, oxblood and blue, plus a brown suede loafer.

Thomas bird range of penny loafers - various colours

Taking care of your loafers

Like all dress shoes, if you look after them they will look good and last longer. So use shoe trees to help absorb excessive moisture, and rest or rotate them so you don't wear them two days in a row.  Use a shoe horn to protect the shape of the heel. Apply a good shoe cream to stop the leather drying out.  Because our loafers have a hand applied patina, we would say to try a neutral cream first to maintain the look.  Maybe try a matching coloured shoe cream to help hide any scuffs or scratches.

The next shoe in your collection?

You just can't go too far wrong with a penny loafer. People that love them really love them. We have one customer who has every colour we make.

Sure there are other loafer styles to consider, like the horse-bit loafer, tassel loafer and plain venitian style, but we always come back to the penny as our favourite. Just find the style and colour that's right for you.

And remember you're not just investing in a shoe, you're getting all that history too.

Thank you for reading this far.  Are you a fan too or a new convert? 

Please let us know and tell us what you think.

All the best till next time,

Thomas Bird

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