Oak Street Bootmakers Trench Boot

Horween Natural Chromexcel

MaticEsq5 months ago

There’s something distinctly different and special about these OSB trench boots compared with my other service boots, but I can’t quite put my finger on what it is. Need to put more miles on them and get this leather darkened up 🤙🤙

Taken on November 18, 2025

See specs

Maker

Oak Street Bootmakers

Shop now

Model

Trench Boot

Leather

Horween Natural Chromexcel

Last

Elston Last

Elston Last: 11.5

Added rose anvil veg tan bootbraker insole in the medium thickness.

Love this last, perfect in the toes and midfoot, a bit more room than I need in the heel and instep, but my heel locks in fine with no slip after break-in. Leather outsoles combined with a mid thickness veg tan bootbraker insole from rose anvil make these insanely comfortable and easy to wear.

Sole

Leather Sole

Order info

Availability: Stock Model

More about this item

As with many of my boots, I purchased these used in like new condition. Break-in was a breeze on the leather outsoles, especially given that I’m a big 240 lbs guy. These rival my Alden Indys for comfort. The leather went from an incredibly pale natural to a much deeper and much more tonal reddish brown with more prominent darkening around the edges of each panel of leather and on the toe caps. Excited to see these continue to patina and deepen in character. I’ll have these for life — easily in my top 3 favorite pairs of boots.

View all 3 comments