Trail Oxford

The Trail Oxford represents Oak Street Bootmakers' commitment to preserving American shoemaking traditions while serving contemporary heritage footwear enthusiasts. Available in multiple leather options including Horween Chromexcel and Domane Roughout, the shoe is fully recraftable and made entirely in the United States as part of the company's mission to maintain domestic manufacturing capabilities.

The Trail Oxford employs genuine handsewn construction methods that evolved from Native American moccasin techniques. Each shoe features hand-stitched toe work using waxed handsewn thread, creating the distinctive moccasin appearance that defines the model. The construction includes waxed cotton stitching throughout and an unlined form-fitting inner design that allows the shoe to conform to the wearer's foot over time.

Built on Oak Street's 555 Last, the shoe uses what the company describes as "the classic New England moccasin last" with medium width and broad toe dimensions designed to provide comfort for nearly all foot types. The fully recraftable construction means the shoe can be resoled repeatedly, extending its lifespan significantly beyond typical footwear.

The primary material option for the Trail Oxford is Horween Chromexcel leather, available in Natural, Navy, and Brown colorways. Chromexcel is manufactured using proprietary techniques developed over 100 years ago at the Horween family factory in Chicago, undergoing 89 separate processes over 28 working days. The leather is hot stuffed with oils and fats to provide softness and water resilience.

Alternative material offerings include Seidel Domane Roughout leather specifically developed for Oak Street Bootmakers and Horween Orion Suede. Hardware varies by leather option, with antique brass eyelets used for Natural and Brown Chromexcel versions and polished steel eyelets for Navy Chromexcel models. All versions include rawhide laces as standard equipment.

The Trail Oxford offers multiple sole configurations, including the brown rubber Camp sole molded to Oak Street's specifications from Brazilian rubber, Vibram Christy sole for enhanced durability, and SVIG Cortina Cork sole for those preferring a more formal appearance.

Oak Street Bootmakers was founded in 2010 by George Vlagos, who is the son of a cobbler and learned shoemaking techniques at his father's shop. George's father, John Vlagos, was born in Greece and opened a shoe repair shop in Wheaton, Illinois, on the day George was born in 1982. George earned a Master's degree from the University of Illinois and taught high school English before entering the shoemaking industry.

The company initially worked with Highland Shoe Company in Maine to manufacture handsewn shoes, as Highland was producing footwear for major retailers at the time. When Highland went out of business, Oak Street Bootmakers purchased all of their assets, including lasts and dies dating back to the Bass and L.L. Bean manufacturing eras, which are now part of Oak Street's archives.

Currently, most Oak Street shoes are manufactured in Maine, with the exception of the Trench Boot, which is made in New York. The company operates from Chicago with a brick-and-mortar store called Independence and maintains its commitment to preserving American shoemaking traditions.

The Trail Oxford experienced significant sizing changes when production transitioned from Highland Shoe Company after Highland's closure in 2017. The current production, now sourced from different facilities, has been described by some users as having a different fit compared to the earlier Highland-manufactured versions.

Historical sizing advice suggested going a full size down from typical athletic shoe sizing, though this guidance may not apply to current production due to the manufacturing changes. The 555 Last maintains its medium width and broad toe characteristics designed for comfort across various foot shapes.

The Chromexcel leather used in Trail Oxford construction requires minimal maintenance due to its hot-stuffed oil and wax content. The leather develops a rich patina over time, naturally lightening and darkening with use to create a vintage appearance without fragility.

Recommended care includes occasional application of neatsfoot oil or greasy leather cream to maintain the leather's condition. Waterproofing sprays should be avoided as they can trap dirt and dust inside the leather, compromising its breathability. Regular brushing with a horsehair brush helps remove dirt and distribute the natural oils within the leather.

For cleaning, a soft cloth is typically sufficient for routine maintenance, though stubborn dirt may require careful cleaning with saddle soap. However, excessive use of saddle soap can strip the natural oils, waxes, and color from the leather, so it should be used sparingly.