Calvin Klein Ulysses Review

9.6 score
[Editors rating (9.6)] = (WalkJogRun) score (9.6)/10

Editor rating: 9.6 / 10
User's rating: based on 0 user ratings
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Combining the classic chukka boot design with a sleek and classy aesthetic, yet durable construction, the Calvin Klein Ulysses Chukka Boot is a must in every men's wardrobe. Featuring a synthetic, non-slip outsole, suede upper, and built-in, shock-absorbing insole, the Ulysses provides excellent quality and comfort, that will last all day long.

Editor's Pros & Cons
  • Suede upper with stitched-on overlays 
  • Flexible synthetic outsole
  • Built-in shock-absorbing insole
  • Soft synthetic lining
  • Great traction
  • Durable construction
  • Attractive design and colorways
  • Narrow fit
  • Runs bigger


For their outsole, Calvin Klein opted for a synthetic material, instead of crepe or rubber, which are the most commonly used materials for chukka boots. While many prefer the rubber over synthetic, this does not mean that the latter lacks quality or durability. Namely, the synthetic sole on the Calvin Klein Ulysses is quite durable, not to mention very sticky as well. Thanks to its slip-resistant nature, the sole grips onto the ground very well, keeping the wearer steady on their feet. Weather does not seem to affect the sole’s grippiness either, as it delivers excellent traction on both dry and wet surfaces, making this chukka boot ideal for year round use. Additionally, the sole is very flexible, greatly contributing to the overall comfort levels of this boot. It follows the natural movement of the feet, not restricting them in the slightest, thus allowing for a bouncy, effortless stride, that will not cause fatigue or sore feet to the wearer, even after long hours of wearing the boots. Reviewers were pleasantly surprised with the durability of the Ulysses, reporting little to no signs of wear and tear on the soles, even after extensive use all year round. The only drawback to this chukka boot is, that its sole is not stitched onto the upper, so resoling is not an option. However, customers did not mind this too much, since the soles last a pretty long time on their own, so they felt like they got their money’s worth.


For their upper, Calvin Klein chose quality suede, similar to the classic Clarks Desert Chukka Boot. It features a plain-toe design with some tonal stitched overlays, adding to the overall aesthetic of the boot. Additionally, these overlays help support the feet and keep them locked in position. The Ulysses is a low ankle boot, which sits comfortably around the ankles, so that it does not create any discomfort or blisters. Unlike other chukka boots, the Ulysses has a fabric tongue, bringing some contrast to the traditional chukka design and making it their own. It has three sets of blind eyelets on each shoe with round waxed laces, creating a more blended in look. Inside the boot, Calvin Klein included a soft sockliner for added comfort, and a synthetic, shock-absorbing insole, for supportive cushioning, which people with both high and low arches can appreciate. However, since the upper is made of suede, it is not water-resistant, so it is advised to spray the boots with a generous coat of water-repellent, if you want to wear them all year round. Suede is also known to get stained easily, so investing in some suede eraser or brush is also recommended. On the positive side, suede generally has a good amount of give in it, meaning, that it conforms to the wearer’s foot shape over time, creating a very comfortable and custom fit for each individual.


Since it was designed to be worn as an everyday shoe, Calvin Klein made sure to include a soft sockliner in the Ulysses, for breathability and added comfort. This sockliner helps keep the feet nice and dry, and stops moisture from building up inside the foot chamber, and causing discomfort. This way, you can wear your Ulysses all day long, without having to worry about overheating in them. They work with both thin and thick socks, making them ideal for year round use, since they will keep your feet cool and dry during the warmer months, and nice and warm during the winter season. Reviewers were generally satisfied with the versatile nature of this chukka boot, and felt comfortable wearing them all year round, without issues with overheating or poor insulation.


Every shoe that is meant to be worn on a daily basis, needs to be comfortable, and the Ulysses does not lack in that department. The suede upper conforms to the wearer’s foot shape over time, following the contours of the feet and delivering a customized fit to the wearer. In addition, the low ankle design does not dig into the ankles, avoiding blisters and discomfort, while the fabric tongue sits comfortably on top of the feet. Inside the boots, Calvin Klein included a soft sockliner, that lets the feet breathe, while a built-in cushioning insole gently supports the underfoot. If that was not enough, the sole is highly flexible, allowing for the natural movement of the feet, making the Ulysses highly comfortable to wear for longer periods of time. Many reviewers wear their Ulysses on a daily basis, and some even wear theirs to work, for long hours, and have nothing but words of praise for this chukka boots’ comfortability.


While it may look like a fancy version of the chukka boot, the Calvin Klein Ulysses is quite durable. The skepticism mainly concerned the choice of the sole’s material, which is synthetic. However, the synthetic outsole proved to be more than enough to tackle extensive use. Its slip-resistant nature adheres to both dry and wet surfaces very well, thus eliminating the risk of slipping induced injuries, and making the boots suitable for all weather scenarios. That said, the suede upper still needs some protection when it comes to water, as it is not water-resistant and stains easily. But once the boots are properly waterproofed, they can be worn without any issues, even in the snow. A few reviewers had these boots for longer than a year, and reported little to no signs of wear and tear, testifying to the durability of the Ulysses. The only issue, that people found, was with the laces tearing prematurely, however, this was easily fixed by replacing the laces, and did not affect their overall opinion about the durability of the boots.


As is the case with most chukka boots, the Ulysses comes in many sizes, regarding length, however, it is not available in wide widths. This is bad news for people with wide feet, as they will have a hard time finding a pair that fits. Another common feature of the chukka boot style is, that their sizing is on the bigger side, so it is advised to purchase at least half a size smaller than your regular size, in order to get the best fit. Sticking to this advice seems to have worked for most reviewers, and according to them, the boots fit perfectly. However, there were a few, who found, that the boots fit true to size. Nevertheless, it is best to stick to the advice and size down.


As mentioned earlier, the Calvin Klein Ulysses is a highly flexible chukka boot, thanks to its outsole. It was designed to follow the natural bending and flexing of the feet, creating a very effortless and springy stride for the wearer. This flexibility is also a big contributor to the overall comfortability of the Ulysses, as it does not fatigue the feet or make them sore, even after long hours of wearing the boots.


Calvin Klein is well-known for their style and high quality products, and the Ulysses Chukka Boot is no exception. While sporting the classic chukka boot silhouette, Calvin Klein included some features to make their Ulysses stand out from the rest. The upper is made of imported suede and has three pairs of blind eyelets, which together with the round wax laces blend in with the rest of the upper seamlessly, for a clean look. The upper also features stitched-on overlays, which add a bit of a contrast and style to the design of the boot. For added class, Calvin Klein included a leather stripe down the heel, while the tongue is made of fabric. The Ulysses is excellent for casual, everyday wear, but can easily double as business-casual, and in some cases, as semi-formal wear as well, adding to its overall versatility. Thanks to its simple, yet timeless colorways, the Ulysses can be worn with pretty much anything, from jeans and a T-shirt, to khakis with a button down shirt and blazer, the sky is the limit with these chukkas.


What sets the Calvin Klein Ulysses apart from other chukka boots, is, that it features supportive, stitched-on overlays, as well as a built-in supportive insole. The stitched-on overlays play a dual role in the design of the Ulysses, one of which is aesthetic, while the other is supportive. These overlays help keep the feet locked in their proper position, when laced-up, thus preventing slipping inside the boots, while the low ankle design hits at just the right place to keep the ankles supported, without creating blisters or discomfort. The built-in insole delivers great shock-absorption to the wearer, as well as provides supportive cushioning, that people with both high and low arches will enjoy. This makes the Ulysses perfect for long hours at the office, or everyday use, as it will not fatigue the feet or cause soreness by the end of the day.


One thing, that reviewers noted, was that the Ulysses is on the heavier side, when it comes to chukka boots. This might be, because, unlike the Clarks Desert Boot, for example, the Ulysses does feature a lining, as well as a built-in insole. What the Ulysses sacrificed in its weight, it made up for it in the form of comfort and support, which many other models lack. All in all, reviewers did not mind the extra weight, as the other features of the boots more than made up for it.

Bottom Line

There is no question that the Calvin Klein Ulysses is a great addition to chukka boots. Bringing a breath of fresh air to the already beloved style of men’s multipurpose ankle boots, the Ulysses is both attractive and high quality. Featuring a suede upper with stitched-on overlays and blind eyelets, this boot looks clean and classy, and at the same time, can tackle a long day’s use. The lining is made of a soft synthetic material, that helps keep the boots well-ventilated, and the feet dry and cool. The Ulysses also comes with a built-in, shock-absorbing insole, which makes it very comfortable to wear for longer periods of time, as it will provide the wearer with supportive cushioning. All of this rests on a durable, non-slip synthetic outsole, that provides great traction on both dry and wet surfaces, making this chukka boot suitable for year round use. Its durable construction, paired with its attractive design, makes the Ulysses the perfect boots for everyday, casual use, as well as business-casual and semi-formal occasions. That said, the sizing of this chukka boot is on the bigger side, so sizing down is recommended. Unfortunately, it is not available in wide widths. However, if you have narrow or medium size feet, and like to look stylish no matter the occasion, then you will not regret investing in a pair of Calvin Klein Ulysses Chukka Boots.