Gentlemen’s Review – Sperry – Authentic Original Lug Chukka

Many, many years ago during the maturation of my personal style, Sperry became my preferred shoe brand for warm weather, as boat shoes became progressively heavy in my shoe rotation. Stylish, very comfortable, and available in a myriad of playful hues; Sperry offered great diversity that complemented my wardrobe. To be honest, I never thought about wearing Sperry shoes beyond the summer months. And I never imagined any other Sperry selection beyond my boat shoes. So when presented with an opportunity to choose a pair from Sperry’s collection for review, I decided to select a boot. Given the cold weather on the horizon, it was the perfect time to test some Sperry boots here in Michigan.

The pair I selected is but one of many choices from a special curated, must-have collection of Sperry favorites from none other than John Legend. The awarding winning (Grammy, Emmy, Oscar, Tony), multi-platinum artist, and now 2020 Sperry Global Ambassador John Legend – yes him. It is very ironic that I selected a pair of Sperry boots from his collection of curated favorites. Perhaps we share the same refined taste in style. Okay – I’m wildly speculating here. Nevertheless, the Sperry Lug Chukka was soon express shipped to me for examination and opinion. First impressions right out the box: These boots appeared more than ready to handle the increasingly chilly terrain of Michigan. So, without further delay, lets dive into the intimate details of the Sperry Lug Chukka.


  • Waterproof leather uppers
  • Handsewn moccasin construction with a fully impermeable protective layer for dryness in any condition
  • EVA cushioning
  • Non-marking rubber lug outsole with molded Wave-Siping™ provides no-slip traction

Sperry boasts a proprietary line of shoe technology branded Techwave. Touted as a fleet of technology for your feet, it encompasses the following components: Plushwave, Rainwave, Stormwave, and Icewave. The Original Lug Chukka is equipped with Stormwave – meaning it promises a no-slip grip, thermal lining, and waterproofing. The lug chukka itself conveys an old-school, tough aesthetic that aims squarely for rugged good looks. The chukka sports 6 traditional punched eyelets with metal grommets (Sperry engraved on each) for added reinforcement. There are two metal hook eyelets at the very top for secure fastening. Four metal eyelets are also horizontally positioned on each side with the signature squared Sperry shoelaces threaded through each hole.

Now, I would not describe the boot as lightweight, but it definitely isn’t heavy as well. The hard rubber sole is relatively thick with a moderate tread that should stomp through snow and handle slippery terrain fairly well. Stitched inside the leather upper is a warm, flannel-like material that covers all of the inside. Warning: Thick socks may make for a tight fit, so a gentleman may want to choose the appropriate hosiery wisely. The layered, protective cloth covering (in a red/black check pattern) is stitched on top of the insole to shield against moisture and water. Regarding exterior waterproofing, the outer seams and stitching appeared clean and tight. The Original Lug Chukka is a relatively comfortable boot with handsewn moccasin construction. However, I must reiterate, a thick sock may make the boot unpleasantly constrictive. The waterproof leather upper is sufficiently supple and soft. The amaretto color (a burgundy-brown hue) responds well to a good polish.


  • Robust design with thick rubber sole that should handle snow and slush sufficiently
  • Supple and soft leather that readily absorbs quality polish
  • Handsome design constructed for rugged outdoor commutes
  • Comfortable fit and feel that does not require breaking in; springy, removable insert for added comfort


  • The flannel-like cloth lining inside the boot may cause a tighter than expected fit if worn with thick socks
  • Squared shoe laces sometimes have the habit of frequently becoming untied
  • Strictly constructed for casual environments, this chukka cannot perform double duty and migrate into the boardroom

The Sperry Original Lug Chukka is designed for the gentleman that favors a rugged, outdoorsy aesthetic. To be sure, this boot certainly has a casual feel and is not built for purposes of a boardroom. This chukka should be paired with denim jeans, khaki pants, and corduroy slacks. The lug chukka is competitively priced at $149.95 along with other boots within the same market. The Gentlemen’s Standard considers this a great investment for a quality, everyday boot when faced with cold temperatures and moderate snow.

For more information, please visit SPERRY for details. For specific ordering details about the Original Lug Chukka, please visit HERE.

Review – Timberland West Haven – The Business Casual Boot

IMG_3129After a few sporadic days of exclusive previews, a gentleman can rest assured that winter is indeed coming. If last year was any indication, one can expect generous amounts of snow and bone-chilling temperatures once again, and dress preparations must be undertaken accordingly. Of course, particular attention will be afforded to a gentleman’s selection of outerwear and accessories. Coats, gloves, and scarves will be deployed to combat what awaits outside. However, today, we’re focusing on an essential sartorial element that is often taken for granted…footwear – namely boots.

Now, with formal or casual options being pretty much straightforward choices; it is the in-between game, the business-casual game, that trips many gentlemen up. Yes, it is not as easy as it may appear. To perfectly execute the styling of a business-casual presentation for boots, a certain balance of refinement and ruggedness must be achieved. To illustrate this point, today we are lucky to have the Timberland West Haven on deck to serve as an example. So, let’s vault into the details before the next snowfall buries us all.

IMG_3139Now, if you are familiar with Timberland, you will already understand that the rugged element is a quintessential staple that pervades many of their models of footwear. However, how is refinement and sophistication addressed when discussing the aesthetic of a business-casual boot? Well, the dynamic amalgam of business and casual succeeds with the commencement of a casual, roughened baseline and then deftly infusing formal elements to soften the tough exterior.

With the West Haven, all the signature rugged components that make Timberland, well – Timberland, are accounted for. The durable cotton laces. The robust, sturdy soles – made with 34% recycled rubber by the way. The supple, pliable full-grain leather. Lastly, the West Haven boasts a zipper that lends a sly hint of attitude as you head into the office. And now, let’s focus on the dressier elements that raises the West Haven’s status from your standard boot to a higher, more dignified pedigree.

Fully present, we have a cap-toe with an adjacent perforated cap design just before the vamp. There are also decorative perforations along the quarters. One can observe beautiful stitching that encircles the entire sole. As previously mentioned above, full-grain premium leather is employed for hard-wearing usage and sophistication.

The boot’s silhouette is streamlined enough to separate itself from the regular chunky boot category, which definitely designates it as office ready. And on your way to the office, a gentleman can be comforted that the West Haven sole provides traction with its exclusive Gripstick™ technology. Oh – the West Haven is supremely comfortable and very forgiving on a gentleman’s heel and sole.


Gent Hints – How To Wear the West Haven

  • The business casual boot is best utilized when worn with trousers boasting tweed, heavier khaki, corduroy, or denim material. The beautiful  marriage of refinement and ruggedness best suits a gentleman when the landscape is replete with snow and slush.
  • The strip of leather that forms a small loop on the back of the boot, it’s called a bootstrap, and it affords leverage when a gentleman is putting on his boots – use it.
  • The standard boot tends to grant additional space for a gentleman’s foot. Therefore, to accommodate the extra room, moderately thick cotton or woolen blend hosiery is recommended.
  • The roominess will probably lead to moderate creasing along flex points, but that should not pose an issue if you regularly polish your footwear.
  • Perhaps a little too rugged for board meetings (unless you are a total rakish rebel), the West Haven is however perfectly suited for your standard office space.


Product Specifications

  • Anti-Fatigue Technology: Made specifically for people who spend long days on their feet, our exclusive anti-fatigue technology is built into the midsole, and uses geometric cone support to provide exceptional standing comfort, shock absorption and energy return all day.
  • Anti-fatigue removable foot-beds with soft synthetic leather covers
  • 100% Organic Cotton Laces: The fabric is made of 100% certified organic cotton (USDA National Organic Program, or equivalent, certified).
  • Premium full-grain leather uppers
  • Silver Rated Tannery: One or more major components use at least 50% leather tanned in a facility rated Silver or higher by a third-party environmental audit. The Leather Working Group judges and classifies tanneries based on energy use, waste production and water treatment.
  • Convenient side zip for easy entry
  • Timberland® exclusive Gripstick™ outsole is made with super-sticky 34% recycled rubber
  • Retails at $180.00
  • Imported


For more information for ordering, please visit the Timberland website HERE for details.


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