Square-toed footwear for a celebration of individuality

Hannibal Derby shoe from Loake

The square toe is the Marmite of the shoe lover! People either love them or hate them or like to try to identify their origin to maybe prove their leaning either way. I have owned several pairs of square-toed shoes and boots. I had no idea they created quite so much ire or desire, so that makes them the perfect subject for a journal article!

Let’s look at the so-called origins of the square toe. Some say it came from a basic construction where there was no difference between the shape of the right and the left shoe or boot. This seems like a rather brick-ish way to go on the style front, but wholly practical, especially for military boots that needed to be pulled on quickly.

Square-toed sandals were also worn in the paddy fields of Japan to prevent sinking as far back as 300 AD, while in Europe, the very pointy and very medieval pointy poulaine style was replaced by a wide-toed shoe known as a footbag! Is it any wonder the square toe lacks a bit of love if it was called a footbag?

Square-toed slippers were fashionable with men and women in the late 1600s and early 1700s, and beyond.

Cowboys also seemed to have had a hand, or foot, in the square-toed fashion. Back in the day, cowboy boots were made for comfort. It wasn’t until the late 19th century that the pointed toe became more fashionable.

There is even mention of a 1940s American footballer who sported square-toed shoes to aid his kicking technique, while they were all the rage for women in a pump or sling-back form in the 1960s and 1970s. Think Jackie Kennedy or the Duchess of Windsor.

Comfort aside, as there is no denying that more space will be easier on the toes, the square toe has simply been a design choice as a shift away from the round or almond-toed footwear. This style has been coming in and out of fashion for many centuries and has seemed to have morphed into the chiselled toe…maybe to off-set the poor PR around the square toe!

The chiselled toe is actually very elegant. Take a look at the Markham Oxfords and tell me if I am wrong. These shoes were made on the Z460 last which gives its wearer a longer toe with sharp edges. We have three chiselled brogues made from this last shape: the Bournwell, Munster and Villiers styles.

We also have the Monkwell monk shoes and our Muswell Chelsea boots.

From other manufacturers, see the super stylish Spencer two-tone brogues from or Darlington Derby shoe from Barker, made on the 443 last, and Loake’s Hannibal brogues.

Like all fashion, it is a choice. A choice that is considered a diversion from the norm is often viewed as a confident look. If you like it (apparently, I do when I think about my footwear choices in the last few decades), then wear it.

Caroline Moore

Caz is our resident wordsmith having trained as a newspaper journalist before moving to the 'dark side' of PR. Since joining Herring, she's become an expert spotter of a chap who needs new shoes or needs to invest in some polish!

Recent Posts

Back-to-school shoe style for work

The Malborough The nights are drawing in now with the next post-8pm sunset scheduled for…

2 weeks ago

What’s the difference between driving shoes and loafers?

Before answering this question, we should maybe explain the origins of driving shoes. They were…

4 weeks ago

The Atlanta

This is purely coincidental but our newest men’s trainer shares the name of an Olympic…

1 month ago

The Sardinia

When we decided we wanted to produce a fun shoe, I am not so sure…

2 months ago

Back to black: Formal shoes for the summer

Black formal shoes are not the first wardrobe item you would expect to think about…

2 months ago

The Ibiza

The Ibiza How do you upgrade a loafer? I mean, they are pretty darn cool…

3 months ago