Judging by the exceptional shoemaking craftsmanship that takes a traditional approach to the art form, you’d be forgiven for assuming Oak Street has been manufacturing footwear for many decades. In fact, the company was founded as recently as 2010 and has developed a sterling reputation among style-conscious men in a short period of time.

This effortless blend of timeless style and rugged durability is evident in the new Oak Street Bootmakers Legend Collection, a limited-edition series of shoes and boots that use high-quality Tuscan vachetta-tanned leather to the fullest. A richly translucent strain selected for its ability to preserve the hide’s naturalistic character, it includes Chukka and Oxford shoes, as well as Cap-Toe Trench and Field Boots.

The Oak Street Bootmakers Legend Collection opens with the Chukka, fitted with a durable, hand-lasted 360-degree Goodyear Welt construction, a limed calfskin vamp, and tone-on-tone stitching. The result is a stylish shoe that elevates the concept through subtle finishing touches, such as grippy rubber-studded soles. These features carry across to the Oxford’s more formal style, made from an Elston last that embodies the spirit of Chicago.

For the boots, the Oak Street Bootmakers Legend Collection features the Cap-Toe Trench Boot, versatile enough for outdoor walks or paired with smart attire for more formal occasions. Alternatively, the Cap-Toe Field Boot delivers a similar overall aesthetic, with a darker leather and complex patina that’s guaranteed to age well as the boot is worn in.

Successfully bringing together centuries-old materials and processes of traditional shoemakers with an eye on contemporary technology, the Oak Street Bootmakers Legend Collection covers essential footwear with flair.

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