A Definitive Guide to Moccasins
November 08, 2023

A Definitive Guide to Moccasins

What are Moccasins?

A moccasin largely is a flat soled shoe made mostly from a single piece of leather that wraps around the sole and is completed with a single seam. Interestingly, the “moccasin” as we know it today has its traditional roots in Native American culture; the word in fact comes from the Powhatan Algonquian language of Virginia. 

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Initially, the colonising Europeans did not much care for indigenous fashion but learnt to appreciate its practical value for the terrain. Moccasins were flexible, they moulded well to the foot, and since their traditional design was high-cut around the ankles, could keep hunters or trappers snug and warm. Crucially, they were durable hiking boots. For these reasons, moccasins made their way into European wardrobes. 

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In the wake of World War II, the classic Native American design found itself replaced by what is now known as the “driving moc”, which corresponds to our Esperanza line of shoes.

Left: Esperanza Black Moccasins | Centre: Esperanza Chestnut Moccasins | Right: Esperanza Burgundy Moccasins

These were a far more relaxed and laid back design that updated the traditional Moccasin to fit the needs of a country newly obsessed with automobiles. Driving mocs are not unlike Native American mocs, except for the fact that they are cut low around the ankle and have rubber tabs on the soles for a better grip. The idea, of course, was that the shoe’s unique blend of flexibility and grip would give one great control and comfort in driving. (The contemporary moccasin still boasts such values). 

It is worth, at this point, distinguishing between loafers and moccasins since people often confuse the two. They both are lace-less, slip-on shoes, but the loafer is often constructed with leather sections first before a sole is added; the moccasin is built the other way around, and begins with a leather piece around the sole of the shoe first that in turn wraps around the foot. For this reason a moccasin has less seams than a loafer. 

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Penny Moccasins, such as our Gregores line, are an interesting variation on the traditional moccasin design.

Left: Gregores Walnut Penny Moccasins | Centre: Gregores Black Penny Moccasins | Right: Gregores Chestnut Penny Moccasins

In addition to the single leather piece they also feature a little leather piece with a wide horizontal slit on top. This slit was in fact meant for holding coins. In the old days, these were used to hold either pocket change for the payphone (which would be quite difficult to pickpocket) or train tickets. Over time the original use-purpose of the slit gave way to fashion statements. It was common to put silver coinage in the moccasin purely to demonstrate ostentation and style. These days, even this aspect of the penny moccasin has become largely archaic; the slit nevertheless adds a nice touch of flair and style to the traditional flat and plain design. 


Why Should You Get Moccasins?

There are two main benefits to getting a Moccasin. Certainly, while at the shoe store, you might be thinking about how to choose between a Moccasin or a more classic Loafer design. While the shoes are similar there are some critical differences that can better inform your choices. 

Firstly, a moccasin is far more flexible. It is very comfortable on the feet, it is very easy to wear, and is tremendously laid back. The slightly wider fit means that it is a very roomy shoe, with a lot of breathing room. A loafer can be a little tighter (since the goal is to have a more refined silhouette on the foot) and hence a little less comfortable. Moreover, this flexibility and roominess means that those with wider feet would benefit from this shoe design. If squeezed in toes are a bother, the moccasin is your go-to causal shoe choice. The flexibility also means that you do not need to worry about creases. 

Secondly, a moccasin fulfils the needs of that always difficult and challenging wardrobe piece: the stylish, dressed-down look that is neither too casual, nor too formal. The moccasin is certainly not formalwear, but it can still make you look sharp and presentable without giving you the feeling of having overdressed for the occasion.


How Do You Style Moccasins?

These are some common colour matches and styles that go well with various Moccasin shades. The key thing about these looks is they are definitely informal outfits. 

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Since the moccasin is a casual look, your go-to bets would range from chinos to white jeans as well as shorts. Generally, keep the colours light and fresh to accentuate that holiday look. For a bit more flair opt for a penny moccasin to really give your outfit a bit more snap. If you opt for black or walnut mocs, off-white, tan or cream pants can provide an understated, subtle look. Completement any of these outfits with relaxed tops: shirts with rolled up sleeves, hoodies, or plain tee-shirts for a nice, pared down aesthetic. 

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The more pressing question for most people is whether to wear long socks with your mocs. The debate within fashion circles when it comes to pairing socks with loafers in general is endless. Moccasins look smart with a hidden sock that bares the ankle. This emphasises a feeling of relaxed, casual wear since it gives off the feeling that you have just slipped into these shoes. There is nothing stopping you from wearing long socks, however. Nevertheless, while they are a trendy choice that is increasingly popular amongst fashionistas, the look can be a lot harder to pull off and is certainly riskier. At the end of the day, of course, the choice is entirely up to you.


When Should You Wear Moccasins?

Moccasins are strictly casual wear. They are to be avoided for formal settings, and this goes for penny moccasins as well; suede moccasins are definitely on the most casual end of the spectrum and should be strictly worn on entirely recreational occasions. Nevertheless, they’re a great way to strategically underdress for a dinner out or a party where casual formal styles are encouraged. 

Another thing to take note of is that the flexible and less structured base of the sole means that moccasins are not ideal if a great deal of long distance walking is required. As driving shoes, they are most comfortable in settings that do not require a lot of mobility and where their flexibility can be a plus. 

That being said, moccasins are a nice way of capping off an outfit that might have otherwise involved sandals, loafers or flip flops; they’re a wonderful way of staying stylish at that weekend get together without being too ostentatious. They are also quite functional, given that one can easily slip them on for a quick, last-minute shopping trip, or for a short drive.