Sole Society Calypso Review

7.8 score
[Editors rating (7.8)] = (WalkJogRun) score (7.8)/10

Editor rating: 7.8 / 10
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Did you know that the over the knee-high boots originally were designed for men? What today is a fashion staple for every woman originated as a men’s boot?

Yes, that’s right. Over the knee style boots first became very popular in the late 15th century. They were first designed to be worn by the men, who were riding on horseback, and not only they were widespread among men in the 17th and 18th century they remained popular in the late 19th century.

And did you know that term bootlegging comes from this type of boot? Yes, during the Prohibition all the men that enjoyed a glass or two of alcohol, were able to hide the flask of alcohol in there over the knee boots without being detected by the police.

But the women adopted the over the knee style boots in the late ’60s, and every major fashion label started having them in their collections. From Balenciaga to Dior, everyone had over the knee style boots in their designs.

But let’s focus on the Calypso model. An over the knee height boot by Sole society that’s both stylish and comfy.

Editor's Pros & Cons

Over-the-knee design

Pull-on style

Padded insole for comfort

Textured outsole for traction


Runs 1/2 Size Smaller


Say hello to the textured resin outsole. Yes that’s right. The Calypso model is designed with a textured resin outsole that just screams comfort and security, and the 1 1/4" heel is not looking too shabby either. Seriously. The outsole and the heel are the perfect addition to the entire boot. A bigger heel would really take away the simplicity and the beauty of the boot, and why make things more complicated? A short stacked heel gives the perfect balance to the massive structure of the shoe, and it makes the walking in the boots a lot easier for every woman, not just to the ladies that aren’t very fond of the high heels. No, the short stacked heel will give your feet the right amount of lift without overbearing the toes and the legs. You’ll fall in live with this gorgeous heel.


Just like with any other great quality shoe, the midsole of the Calypso model is padded for extra comfort and security and there’s a textile lining in the footbed that secures that comfort the right way. You’ll be surprised what a padded footbed can do to any type of shoe, let alone a massive construction like the Calypso model that requires much of your leg efforts. No, the padding will give your feet (and rest of the leg) the much needed comfort and will make thing easier for your while wearing the boots.


Oh, the upper of the Calypso boot. It’s gorgeous, isn’t it? So buckle up, there’s plenty to be said and written about that upper. Where to begin? From the quality suede used in almost the entire upper or the textile lining on the inside of that upper? Well, the Calypso model is a slip-on style boot with an over-the-knee design. The shaft of the boot measures 20 inches and will accommodate ladies with wider calf as well. Yes, the shaft and the entire portion of the upper can be stretched to fit a leg with wide calves so, that’s another plus. The stretch is thanks to the back panel of the boot, and it’s solely responsible for expanding the boot to fit several types of calves. Calves that are wider and that are much thinner.

The width of the toe comes in medium size, and that stretchy panel mentioned earlier not only has practical purposes but also gives the shoes their beautiful contrast in a visual sense. The color of the upper comes in the black and lighter mushroom color and whichever you chose, you won’t be disappointed. Both of the color varieties look great on just about any type of woman.


What’s the best way to provide a comfort in an over the knee style boot like the Calypso? By having great outsole and short barely there heel. Both of them combined have the best comforting abilities, a pair of shoes can offer, and you should take full advantage of that.


Much of the support in the Calypso model really comes from the padded midsole. Because the entire boot is heavier, and sturdier in size, the support really has to come from within. The padded footbed is there to insure the foot rests properly, and that the entire foot is supported in the right way thanks to the midsole and the gorgeous stabile outsole.


The true sign of quality is the fantastic craftsmanship that went in the making of the shoes, and the quality of the materials used here speaks volumes about the durability. These boots will last, and they’ll last long. Not weather can ruin them and they’ll make sure to keep your feet warm, secure and your feet durable to withstand any type of weather conditions. They’re ideal for cold rainy autumn months and even colder snowy winters, and you’ll find yourself wearing them all the way to the spring.


The Calypso model is not known for the flexibility, but because this is a more winter style of a boot, it doesn’t need to be flexible. The round toe design and medium wight of the midsole allow your feet to move properly within the boot without the feeling of confinement.


What the boot lacked in flexibility, it sure makes up in stability. Seriously this is one of the most stabile boots in the Sole Society assortment. And in big part, that stability is provided by the textured resin made outsole, padded insole and that gorgeous suede upper. Reinforced with stretchy panels, the back of the upper allows the calf to move freely within the shoe and for you to feel comfortable in any moment. Because this is a slip on type of a boot, the biggest part of the stability in the calf area, comes from the thick suede in the upper. It’s strong, sturdy and provides a great grip to the entire leg.


The airflow in the Calypso style of the boot is limited solely to the aeration provided by the suede leather. The material such as cow leather has great moisture wicking properties, and gives the boots a great deal of filtration. So, the moisture and the odor will become a thing of the past, and a little push in that direction will give a synthetic lining that is coating the inside of the upper.


The Calypso model is highly durable in almost every terrain and in every type of weather condition. The sole purpose of the boot is to protect your feet during the icy cold weather conditions of the winter, and the Calypso will do just that. The thick resin outsole and the gorgeous heel will make your feet comfortable on almost any type of terrain and in almost any weather.


The resin outsole does help with the traction properties of the boot, but the ridges of that resin outsole are not that deep, which means, that although some traction is provided, it’s not extensive on the big portion of the upper and you do need to be careful when walking on smooth, slippery or wet surfaces.

There are much deeper ridges in the heel of the boot, and that part of the calypso model is most equipped to deal with the traction. The heel will keep your feet secure and protected, and it can balance the lack of ridging done in the other part of the outsole. But given that the entire outsole of the Calypso boot is made from textured resin, the traction will become significant in almost every situation.


Over the heel style boots are a great accessory for every type of fashionable ladies. Long gone are the days when these style of boots were made solely for men, and with the proper outfit, they will look great on just about anybody. Regardless if you’re tall, short, skinny or little of the heavier size. The shaft of the outsole is stretched by panels and they can accommodate the ladies with wider calves. The Calypso boot looks great with a pair of tight jeans, some leggings and a great winter dress or even a mini skirt that will accentuate your legs. You can wear them for your daytime events, you can wear them to work, since they’re work appropriate and they’re amazing for your nighttime outings. They look great with a more casual outfit, during the day and more elegant sophisticated outfits for a glamorous night look. And why know why? Because of the plainness in the design. Yes, the Calypso boots don’t have embellishments, tassels, fringe or any type of hardware that would put them in a mold and categorize them for exclusively nighttime or daytime wearing.

No, Sole Society were careful not to put the Calypso shoes in any bracket, so you can wear them in any occasion. They’ll look amazing with just plain jeans and a great cashmere jumper, and they’ll look fabulous with your favorite dress that you’ve been dying to wear all winter. Because when you have a great pair of boots like the Calypso models, you don’t really need to be restricted by any occasion to wear them. They have the ability to spice up otherwise dull outfit, with a dash of simplicity and elegance, and to make your day and night a lot mo comfortable and fashionable too.
Key features:

Bottom line

A great and simple over the knee boot that’s both stylish and comfortable? Yes it exists and it’s called Calypso. The Calypso model by Sole Society is a pull on style type of boot that has a textured resin outsole, polyester lining and cow suede upper. The design of the boot is kept simple without any embellishments, which only adds to the versatility and durability. You’ll be wearing the boots long after you buy them, and you’ll be wearing them with almost every outfit in your wardrobe.
The only thing that would really improve the entire shoe is the addition of a zipper to the side of the boot, for an easier way of putting on the shoes on your legs. The zipper along the line of the upper would improve things greatly, and a lot of the ladies with thicker calves can enjoy the boots as well. It doesn’t have to be long zipper, just enough to make the opening of the boot a lot easier for every woman.

The shaft measures 20 inches as they are right now, and the company assures that they’re meant to be worn by every type of lady, but a zipper that would open the boot down the length of the upper would really make things easier for a lot more women. But that doesn’t mean that they’re not amazing in the state they’re now. In fact the calypso model is nearly perfect. It’s versatile, stylish, and elegant and will suit every type of woman. A stylish fashionista who doesn’t like to give up wearing her miniskirts and the practical mom on the go that just needs the comfort and protection that a slip on shoe like this provides on a daily basis. Because when you have small kids, and you’re always in a hurry, shoe strings, zippers and buckles are just a waste of precious time that would otherwise be focused on something else.

The Calypso style boot by Sole Society is one hell of a boot. Practical, stylish and versatile. You’ll enjoy every moment spent wearing it.