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Sleek Engineer Boots – Five Plus One

Five Plus One is our weekly series of buyer’s guides. We pick a specific category and dig up five great options along with one that’s a little outside the norm.


If there is one style of boots that is quintessentially American, it’s the Engineer Boot. They first appeared in the late 1930s and grew swiftly in popularity over the next decade, in part due to their sleek silhouette and flat toe. We love these classic engineer boots, but unfortunately the vast majority of engineer boots produced today do not look like the boots of yesteryear. Most of them are made on bulbous lasts and feature reinforced toes, a far cry from their 1940s counterparts.

Luckily, a handful of companies produce vintage-inspired engineer boots, and we’ve rounded them all up so you don’t have to. Full disclosure, sleek engineer boots don’t come cheap — while we do our best to find a budget option, sometimes that just isn’t possible. We love our Red Wings, Chippewas, and Wolverines, but we’d be doing you a disservice if we told you that the engineer boots they produce today are elegant and streamlined. That said, whether you’re prepared to drop some serious dough or just appreciate quality boots, you’re sure to find something on this list that is to your liking.

1) Wesco for Iron Heart: Build 5 — 9″ Boss on the Patrol Toe Last

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First up is a pair of Wesco’s Boss Engineer Boots — we might not have had room to feature them in our Stitchdown Boots – Five Plus One article a few weeks back, but that doesn’t mean we don’t love this Pacific Northwest bootmaker. This build, which was made exclusively for Iron Heart, features a double midsole, extended vamp strap, custom brass buckles, and Wesco’s “Brown Domain” leather, which is in a roughout/smooth configuration.

Like many of Wesco’s popular builds, this one is made on the flat-toed “Patrol Toe” last. If these don’t quite strike your fancy, don’t worry — Wesco produces fully custom boots as well. Their made-to-order boots start at around $400, but each modification has an additional fee. And as anyone who has ordered a pair of custom boots can attest, the cost can really creep up.

Available for $950 from Iron Heart UK.

2) John Lofgren: Engineer Boot in Natural Chromexcel

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It’s impossible to talk about engineer boots without talking about John Lofgren, so why even try? He makes great boots out of some of the most popular materials. This model features a slightly rounded toe, yet it still appears very sleek, in part due to the boots’ forward stance. They are made in Japan with Horween’s Natural Chromexcel, a double midsole, Australian steel buckles, a 270° storm welt, and woodsman’s heels.

Available for $895 from Self Edge.

3) Santa Rosa: Flat Toe Engineer Boot

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Next up is a pair of Santa Rosa‘s Flat Toe Engineer Boot, which is offered in four different shades of Latigo leather. This boot sports elongated vamp straps, quadruple-stitched counters, a steel shank double riveted to the midsole, and a double stitched Biltrite half-sole. The main thing distinguishing this pair of boots from the others on this list is the short, non-tapered heel. Taller block heels are prone to heel drag, which is why thick, stacked heels are normally tapered into Cuban heels — Santa Rosa sidestepped this problem by simply using a shorter heel.

Available for $795 from HTC Hollywood Trading.

4) Viberg: 8″ Engineer Boot in Black Bison

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Viberg has made some attractive Engineer Boots in the past, but this latest iteration is a real home-run. It features beautiful, black bison leather, a stacked Cuban heel, extra-large gussets, and Japanese roller buckles. Unlike many of the other boots on this list, the Viberg Engineer doesn’t feature a double midsole or extra long straps, and the lack of these details creates a very different boot. Viberg further differentiates this boot from other offerings bu using stitchdown construction, which, although not traditional for engineer boots, does help to create a sleek silhouette.

Available for $770 from Viberg.

5) Mister Freedom: Roadchamps

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Mister Freedom’s Roadchamps are some of the best vintage-styled engineer boots on the market. They’re made on an extremely flat-toed last, feature slightly elongated straps, an all leather sole, and a Cuban heel that is topped with a vintage Cat’s Paw heel. All of those details are great, but what really sets these boots apart is the leather. Although it’s black at first, the black dye is only on the surface — beneath it is a medley of brown, olive and chocolate dyes, which will begin to peer through as the boots are beaten up and start getting a patina. Once those undertones start to show through, they’ll be picked up by the olive gusset and rolled top.

Available for $950 from Mister Freedom.

Plus One – Role Club: 10″ Engineer Boot in Olive Steerhide (Custom Orders Only)

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If there is anybody who understands what details make a good vintage-style engineer boot, it’s Brian Truong (aka Brian the Bootmaker), owner and sole operator of Role Club. A little over a year ago he started offering his own line of custom boots, which are available in brown and black horsehide, as well as olive steerhide (pictured), and the boots he has produced in that time have been nothing short of exemplary.

They are lasted on his 0-200 flat-toe last, and are handwelted without the use of gemming. Like many of the other boots on this list, this pair features elongated straps, a woodsman Cuban heel, and quadruple-stitched counters. However, this boot has some details not present anywhere else on this list, such as the use of Role Club’s custom branded halfsoles and heels, which are stylistically similar to vintage ones from Cat’s Paw or Biltrite. And that line going down the middle of the vamp? That’s intentional too — it’s called a toe track, and, although originally an side effect of the lasting process, it is now a sought after detail. The amount of thought that went into every detail of this boot is mind boggling, so I encourage you to check out the full specs, even if you don’t intend to make a purchase.

Available for $980 from Role Club.