(Engineer) Boots the House Down

How I stopped worrying and learned to love the boots with a secret sexy history

Please watch the video… read below for even more context!

I’m a born-again virgin when it comes to Engineer Boots.

I bought my first pair of Engineer Boots secondhand off ebay when I was probably 20 years old. They were a pair of Red Wings, brown, with a low-ish heel. I, like many new Engineer Boot customers, had seen the iconic photos of Dean and Brando and wanted to emulate the look. Even though my selvedge denim jeans were slim (and barely fit over the chunky boots) I made them work.

I phased them out pretty soon after I began working at Self Edge LA. Engineer Boot wearers seemed like they could be easily divided into two camps: bikers and posers.

The bikers were kind of what you’d expect. Grizzled, tanned, and clothes worn hard by days on the back of a motorcycle. The posers were a broader spectrum. I remember one guy (who drove a Prius) would saunter in wearing the same uniform as the bikers, down to the leather gloves in his back pocket - the only difference, every square centimeter of his outfit was pristine. There were other posers of varying stripes - but I decided then and there - I don’t think these boots are for me.

I put the boots so far out of my mind, I almost didn’t remember I’d ever worn them. I clowned on them a few times over the years, but then the world changed.

Modern Day

I feel like I woke up one day and Engineer Boots were cool again. In hindsight, I know it was a slow burn. It started on the women’s side with a Frye boot resurgence, which transferred over to the men’s side and then caught fire among big pants wearers. Men had already been primed for boot-wearing by the avalanche of new zip Camion-style boots and then it was a slippery slope that led from Fryes to harness boots until we reached the logical conclusion: Engineer Boots.

Seth in Chippewa Engineers and the pants he designed. He actually uses those gloves too.

The guy who kept influencing me to give them another chance was Seth Lopez. I’ve written about Seth before (and he is featured in our video), but I became aware of him when he collaborated with The Hidden Rivet. The denim trousers they made were basically perfect and with its wide leg, paired well with heavy-duty pull-up boots. Seth also rode a Harley, which made all of his clothes feel a little more convincing. It felt like the old biker/poser paradigm was fading away a bit. I decided to give the boots a second chance.

The History

Engineer Boots have an extremely convoluted history. Even John Lofgren, a renowned boot designer, parrots a mostly-debunked theory about where the boots came from in a 2015 Heddels interview.

If you go deep into any Engineer Boot forums, you’ll find dozens of devoted boot-nerds debunking the original myth that the Engineer Boot was first used by locomotive engineers. They’ll produce photos from the period of various train-workers (not wearing Engineers) or advertising materials from the period that seem to suggest they were used for a different job entirely.

When I began my own history, I realized it was mostly useless to dig too deep into their origins. All we know is that they were invented in the mid-1930s. Possibly first by Chippewa Boots - or else Sears (may have still been manufactured at Chippewa) or by Wesco. (See, it’s a little muddy.) We don’t know precisely who the boots were for - and everyone has their own masturbatory theory, BUT we do know they were tremendously popular with motorcyclists in the 1950s.

The (secret) History

Before the Second World War, riding a motorcycle wasn’t particularly badass. But as servicemen returned home, jaded and rebellious; the leather jackets, jeans, and motorcycle boots they wore - were increasingly associated with bad behavior. The above photo was from the Hollister Riots, which went on to inspire The Wild One.

But not all men joined motorcycle clubs for the same reason. Some men joined as a way to be near other men - and not just as friends. Closeted gay men from the 50s onwards consistently found motorcycle clubs to be a convenient cover for them to meet other men. And slowly, as the world moved on from the Brando image, which many in the straight world viewed as the epitome of heterosexuality, gay men kept it alive.

Tom’s Men: a drawing by Tom of Finland

As fashions changed and straight men increasingly adopted flamboyant polyester attire, gay men kept the uber-macho biker look going. Tight jeans, leather jackets, and of course, engineer boots all looked great and could covertly communicate one’s sexuality without endangering yourself. These archetypes are most famously catalogued in the works of Tom of Finland. Not just porn, the macho male characters served as inspiration to gay men in the postwar years: showing them as proud, strong, and devilishly handsome.

Buying My Own

I admittedly didn’t know all this history yet when I set out to buy a pair a few months ago. I thought the story would be better if I met with an expert bootmaker, so I went to Role Club in South LA. Brian Truong, known online as Brian The Bootmaker, makes all manner of bespoke boots, but is most famous for his engineers.

For the princely sum of $2300, I commissioned a fully custom pair of horsehide engineer boots. I also got to spend a whole day with him in his shop, watching him at work. His boots typically take over a year to make it to the customer, but he rushed my pair and OH MY GOD. I’ve never worn anything as nice in my life.

Boot sale at the Tom of Finland House

You might turn your nose up at such an expensive custom pair of work boots, but I learned from this project that custom boots are part of the rich history of the Engineer Boot. You see, many of the gay men who rode in biker clubs and were fans of Tom of Finland’s work spent their hard-earned money on elaborate custom versions of the boots made by Wesco and other great American brands. Whether simply for riding - or because they were a part of the leather fetish scene - I think it was gay men who propped up the heritage menswear boot brands, when many straight consumers turned their backs on them for cheaper goods.

Breaking the Biker/Poser Paradigm

The more I learned, the more fascinated I became. It turns out, the Engineer Boot is about much more than bikers and posers. Despite their murky origins, these boots came to symbolize an ideal masculinity for so many people. A masculinity that inspired gay and straight men alike - and helped them all look sexier.

Shopping Guide

• Vintage Chippewa Boots - Seth swears by ‘em and there are tons around. ($200-$500)

• Modern Frye - Made in the USA. Nice heel and rubber outsole. ($498)

• Wesco Boss - A classic brand. One with deep ties to the gay scene. ($500-$600)

• Red Wing - Tea-core leather and good heel. ($549)

• White’s Cykel - Very classic iteration. ($675)

• White’s x James Dean - An engineer boot sans strap. ($1,195)

• Role Club - Brian makes the best, but don’t rush cuz it’s a grail ($2300)