• Top

    Low Top

    Extremely popular sneakers because of their price range, versatility when it comes to style, and freedom of movement. Almost everyone is guaranteed to have low-top sneakers in their shoe rotation.

    Mid Top

    Mid-top sneakers extend toward the ankle for a little more support and hold. These lie somewhere in the middle between low-top and high-top sneakers in terms of usage and popularity.

    High Top

    Sneakers with collars that go above the ankles for optimal hold and support are some of the most sought-after models in lifestyle shoes. Most of these shoes take their roots from basketball and have easily or fashionably crossed to mainstream wear.

    Good to know

    Regardless of cut, it's always good to start with sneakers that can be worn for the daily grind, also called as "beaters" by some, as these are usually cheaper, easy to clean, and still gives that lifestyle "edge" before going for those wallet-thinning models.

  • Inspired from


    Sneakers dominantly take their heritage from running, basketball, skate, tennis, training, hiking, and football. Still retaining a few of their performance-based technologies, these sneakers have transcended their respective niches and have successfully and popularly transformed themselves as staples of fashion footwear.


    Sneakers designed for a laidback, "cool" vibe that is built for lifestyle wear right from the get-go.

    Good to know

    Brands are now blending elements of performance and casual appeal in basically every sneaker. One can hardly go wrong with a sports-inspired sneaker or a simple casual shoe.

  • Collection

    Good to know

    Shoes sharing the same inspiration, history, materials, or technologies are routinely assembled under one compilation for the convenience of those who may wish to categorize or label their own collection as such. The classic collections like the Adidas Originals, Air Max 1, Air Force 1, new balance classic sneakers, and the Classic Leather head the pack of frequently asked about collections.

  • Price
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Timberland Adventure 2.0 Cupsole Alpine Chukka History

Founder Nathan Swartz began working in the footwear industry in the late 1920s. In 1955, he bought all the shares in the Boston-based The Abington Shoe Company, bringing his sons with him to the business. Contract work for manufacturers was their main operation back then, but it all changed when they introduced the injection-molding process in the shoe industry. The technology allowed the company to remove the need for stitching the sole to the upper.

Soon, the business turned to the production of completely waterproof boots for both cold and warm weather. By the late 1960s, the company had grown so much that they transferred to Newmarket, New Hampshire. It was here that they came up with a waterproof leather boot called “Timberland” in 1973. It quickly became so popular that the brand decided to change its name to The Timberland Company.

It was also in the 1970s that boat shoes and casual footwear were added to the brand’s boot lineup. One shoe from the company’s casual series is the high-top Timberland Adventure 2.0 Cupsole Alpine Chukka. It's inspired by the brand's distinct outdoor roots, as can be seen in its smooth upper, made up of premium leather. Its design has a touch of elegance, yet it also has a rugged appeal that speaks of adventure. 

Timberland Adventure 2.0 Cupsole Alpine Chukka Style

Trademark Timberland details elevate this shoe to a level of sophistication that makes it appropriate for any casual activity. Whether it's for the streets or the office, these kicks are worth a place in anyone's wardrobe. Urban outings or weekend getaways also become more stylish with a pair of these sneakers. Pants or shorts paired with t-shirts and jackets complete these shoes’ flair for urban adventure. 

Fit & Sizing

A durable fit is ensured by the premium leather upper of the Timberland Adventure 2.0 Cupsole Alpine Chukka. For this model, men’s sizes in medium width from 7-13 are offered. It fits true to size although it's been found to be larger than usual by a half size. Laces and D-ring eyelets maintain a snug fit. Lastly, the high-cut collar provides excellent protection for the ankle.

Notable Features

An upper made up of premium nubuck leather that comes in several colors lends a classic appeal to the Timberland Adventure 2.0 Cupsole Alpine Chukka. Its collar is padded for more comfort, while its mesh lining ensures ventilation. The Timberland Tree logo is debossed on the side, while the brand name is found on the tongue and heel tab.

Additional Info

  • The EVA footbed offers support and comfort.
  • Comfort is also delivered by the cupsole.
  • Its rubber outsole has a siped design that makes it excellent for slip resistance.
  • This model was also crafted with some eco-conscious materials to reflect the brand’s commitment to the natural world.