We’ve sourced and sold motorcycle boots for over a decade, and that experience fed directly into the design brief for our first in-house Union Garage boot project. The goal: offer genuine protective features, but hide the armor in discreet styling.

The Derringer delivers by marrying centuries-old bootmaking techniques with modern-day D3O armor, plus some extra-credit reinforcement at the heel cup and toe box.

All that tech is concealed in a traditional yet unique looking low-cut silhouette that pairs an oiled black top grain leather shell with an inviting soft tan calfskin interior, and a grippy low-profile Vibram sole.

To produce this boot we collaborated with Umberto Luce, a motorcycle boot brand and manufacturer in Leon, Mexico. After several rounds of samples and many miles logged, on and off the bike, we have a final product that we're proud to put our name on and add to the shelves.

Fully Loaded

Despite a diminutive silhouette, the Derringer boots come fully loaded with protective features.

Hand-shaped D3O inserts protect the wearers’ malleoli (aka ankles), and there’s an additional length of the magic orange armor in the tongue, set behind the laces, to further swaddle your feet in safety  

Most of the development process for the Derringer was focused around fine tuning the reinforcement of the boot’s toe box and heel cup. This was done by adding sequential layers of celastic until we achieved a sufficiently thick shell of protection; superior to many other boots in the same category.

Celastic is a plastic impregnated chemical fabric that is flexible to work with, but once activated can be molded to a preset form, which then sets up to provide a permanent protective shell.

Besides beefing up the thickness of this material, we also extended the profile of the protective toe box along the outside edge of the boot, giving a little extra coverage to the 5th metatarsal—aka the pinky toe, the most commonly broken bone in the foot.

Low Profile

No shifter patches. No easily discernible exterior branding. No exclamation points.

Even the tread on this boot is low profile: shallow but grippy, with a heavily crisscrossed pattern in the center that’s less pronounced on the perimeter. This Vibram sole gives the boot ample grip, while still allowing it to slide into a number of social situations without looking like an overbuilt motorcycle boot.

Of all the boots we carry, this is among the least likely to be pegged as a protective motorcycle boot when spotted out in the wild. It fits well under just about any jeans, riding pants, or non-motorcycle pants, and the toe profile fits easily under any shifter we’ve tried.

While a shifter patch would offer an extra layer of leather between the shifter and the toe, the reinforced toe box provides plenty of protection from even the sharpest shifter knobs, without sacrificing feel.

Work, play, bike, bar. Dinner out, sure. Dancing? Not until you’ve broken them in well. More on that below.

Clean Cut

The upper portion of the Derringer boot covers both ankles with built-in D3O armor, but the back of the boot is cut low, making it comfortable through a wide range of flexion, meaning it’ll work well with a variety of bike styles and relative peg placements. This feature also makes for an easy-wearing, everyday boot.

But make no mistake, this low black boot packs  as much or more protection than most similarly styled taller lace up options we’ve seen.

In fact it’s so supportive, we’re shipping each pair with a shoehorn, both to make it easier to get on/off, and to help protect the boot from a hurried owner who is just trying to jam their boots on to get out the door. As with any boot, especially one with some much extra tech baked in, it’s possible to crush the pre-formed heel if you’re not careful getting it on. Don’t ask us how we know.

What it is

The Derringer boots go where you go. They’re an everyday option that’s comfortable in an office, out on the town, and on the bike.

And the name? A Derringer is a small but powerful and easily concealed pistol, and we felt an appropriately catchy analogy for these boots. Made famous as the type of small handgun used to assassinate Abe Lincoln at the Ford Theater, the Derringer boot is a diminutively sized, yet very effective option worthy of adding to any arsenal.  

All the Derringer's reinforcing features are cloaked in an otherwise traditional leather boot construction that's based around another throwback to the 1860s: the Goodyear welt, which means these boots can be repaired, resoled, and reconditioned to extend their service life far past cheaper, disposable boots with imitation welts—eg: fake stitching designed to look like high end boots.

What it's not

> The Derringer is not waterproof.
This is by design. Sure the shell is made of oiled leather and there is a tongue gusset up to the top of the eyelets, but we intentionally didn’t want to make this another waterproof boot with a membrane tucked in between the shell and the liner. 

Instead, we opted for a traditional construction that breathes a bit and won’t cook your feet on hot weather rides. We didn’t prioritize hours of rainy highway stints, but instead focused on making a boot that can be worn day in and day out.

> The Derringer is not not the most protective motorcycle boot we sell.
If you look at a more purpose-built boot like the touring/offroad Sidi Adventure 2, or at any quality track boot, you’ll note they all share some sort of mechanical hinge to prevent hyper extension, and to provide an additional exoskeleton of plastic support between the rider and the road. They’re also just about impossible to walk normally in. Think: ski boots.

These bigger boots are the Kalashnikovs of the motorcycle boot category, overt weapons of war. By comparison, the Derringer are a discreet concealed carry option, a little easier to live with in everyday life. 

And while this boot is not CE rated, we feel that it's about as protective, and better built, than many similarly styled European offerings that do come with a CE rating.

> The Derringer is not the most comfortable boot you’ve ever tried on. Not at first.
But if you can get past the showroom (or home living room) test, and commit to breaking them in, they will conform to your feet over time.

Shoutout also to the DuraEVA foam sandwiched between the Vibram tread and the leather welt, which contributes to comfortable walking and also dampens road vibrations through the pegs.

But at first there will be a (potentially) tough love honeymoon, where the cork in the sole molds to your foot and the leather molds to your particular foot as you break the boots in.

Why we made them

Part of the motivation for making the Derringer has been years of seeing riders roll through the shop wearing traditional leather boots that look the part, are comfortable to walk in, but offer no real features or protection while on the bike.

The Red Wing Iron Ranger, for example, is an iconic boot and a beautiful specimen—but it is a technically a farm boot, not in any way meant as a motorcycle boot.

There are legions of companies making their own version of a classic leather work boot (Thursdays, Frey, Chippewa, on and on), but most—yes, even those that use motorcycles as marketing backdrops—fail to include much if any real protection.

The Derringer, with its unique silhouette and distinctive style, might not be everyone’s cup of tea. But we think it’s a handsome option and are happy to add it to the catalog as our first house-brand motorcycle boot.

Sizing and break-in notes

Before releasing these boots we chalked up more than a thousand miles of riding on various bikes, and on the flip side, many miles of pounding pavement on foot—going up and down stairs (there are 42 from the street-level front door to our showroom); taking the dog for walks through wooded trails, sandy beaches, and snow. We can report that they do break in beautifully, if you’re willing to put in some work. 

We recommend “tuning” the fit with just the right sock. Depending on how much room your chosen size allows, a light or mid-weight Merino option works great for regulating moisture and temperature, and providing enough buffer against the interior contours of the boot.

Speaking of socks, pick a pair you don’t love for the first few wears, as we’ve experienced some color-bleeding from the tan interior during the first few wears. You’ve been warned.

These boots aren’t perfect, but we love them for their unique look, their combination of functionality and protection, and their everyday wearability.

*The Derringers are offered at the outset in a standard D width. Additional sizes, and custom wide options, will be available for future restocks. Inquire within or use our contact form.