Oak Street Bootmakers Black Dainite Trench Boots – $462

The trench boot, sometimes known as the “Pershing boot,” was a combat boot used in World War I by British, American, French, and Belgian forces, made for the cold mud of trench warfare.

The 1917 Trench Boot was an adaptation of the boots American manufacturers were selling to the French and Belgian armies at the beginning of World War I. In American service, it replaced the Russet Marching Shoe. The boot was made of tanned cowhide with a half middle sole covered by a full sole, studded with five rows of hobnails. Iron plates were fixed to the heel. It was a great improvement, however it lacked waterproofing, leading to trench foot.

WWI-Soldier-with-Trench-Boots-Resized In January 1918 the Chief Quartermaster for the U.S. Army met with a board of officers at American Expeditionary Force Headquarters to make recommendations in order to improve the footwear of soldiers. The findings of the board were sent to General John Pershing, who approved the proposed changes. Shortly following, the improved 1918 Trench Boot, also called the “Pershing Boot,” was first issued to personnel. It used heavier leather in its construction, and had several minor changes from the 1917 Boot, including a thicker sole and improved waterproofing. – Adapted from Wikipedia


About Oak Street Bootmakers

George Vlagos, founder and designer for Oak Street Bootmakers is the son of a cobbler. By an early age he was apprenticing in his own father’s shop where he learned the craft of shoemaking. Now George passionately seeks to preserve the heritage of fine shoemaking through exquisitely designed, expertly crafted shoes. Their website mantras are “Handcrafted in America – Designed for Longevity”.




Oak Street makes a wide variety of attractive shoes and boots. In my initial discussions with George, we decided to review the Oak Street Bootmakers Black Dainite Trench Boot. This is one well-built boot! It features:

  • Black Horween Chromexcel Leather
  • True Goodyear Welt Construction
  • Dainite Soles
  • Stacked Leather Heel with Dainite Toplift
  • Calfskin Vamp Lining
  • Full Leather Laces


These boots are fully re-craftable and they’re made in the USA. If you’re a regular here at BestLeather, you already know our thoughts on Horween’s Chromexcel Leather. It’s highly durable and an excellent choice for a boot given its high sheen. This is the first pair of boots or shoes that I’ve worn with Dainite soles or heels.


Here’s a little snippet from Oak Street’s website about their construction: “Built on our Elston Last – a unique last providing exceptional fit and shape. Developed to embody the character of Chicago, the Elston last is engineered specifically for the trench boot providing the comfort yet durability demanded of the every-man.”


There is a bit of a break-in period with a boot constructed with a Goodyear welt and so much leather. So, be sure to plan on wearing these for short periods of time the first few outings you don them on your feet. After a few dates with my wife, church visits, and excursions to client offices, I had these boots right where I wanted them. Now, I can wear them all day without issue. In fact, they are now very, very comfortable.


Another thing to note about the Trench Boot – they have eyelets all the way up. This means that you will need to lace and unlace them each time you take them on or off. It’s a little time consuming, so just plan ahead. I also found that since these boots do not have a heel loop, it’s easier to slip them on using a shoehorn.


Oak Street’s boots seem to run true to size as the fit was spot on for me (I generally wear a size 12 and the boots I received in size 12 fit perfectly). The sole and heel are comfortable and provide excellent traction. After reading a little about the Dainite sole and heel, I took a bit more notice of the fact that they truly don’t pick up dirt or rocks, yet still maintain good contact feel, and are non-marking.



Have you seen the pictures? (Oh that’s right, you only come here to read the words.) These boots are stunning and look fabulous. This is going to sound like I’m describing a sports car, but here goes: The Oak Street Bootmakers Black Dainite Trench Boots feature clean lines, smooth finishes, carefully crafted curves, and an excellent combination of materials.


The contrast of the deep black Horween leather and brown color of the sole’s components combine to create a very appealing look. Someone inevitably comments on these boots every time I wear them. Every. Single. Time. I’m sure that the other versions of their Trench Boot will garner the same attention. However, I’m partial to this black pair – I think they’re fantastic.



The Oak Street Bootmakers Black Dainite Trench Boots should be considered a Buy It For Life item. Initially that $462 price may sting a bit, but only a bit….because you’ll quickly find that these handcrafted boots are well worth every penny and will truly give you a lifetime of comfort and style. The Oak Street Bootmakers Black Dainite Trench Boot pays tribute to a time tested design that has been around for almost a century and is sure to remain popular for many decades to come.


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  1. Nice looking boots! How would you say these stack up against the Wolverine 1000 Mile or Red Wing Beckman boots?

    • Hi Matthew – I like the Oak Streets and have worn them quite a bit since receiving them for this review. I don’t have either pair of the boots you refer to, but we have done a review on the Wolverine 1000 Mile Boots. I do have Red Wing Iron Rangers and personally, I like that style a bit more. The Oak Streets are beautiful and, in my opinion, much more ‘refined’ than the Iron Rangers. I don’t like the time it takes to lace the Oak Streets all the way up to the top. If they had speed hooks on the top, I’d probably wear them every day (at least every day that lends itself to boots and black, in particular). They’re extremely well made and definitely beautiful. I’ll be posting a follow up report on these boots in the next couple of weeks.

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