We are officially just 10 days away from the Chicago Super Trunk Show x Stitchdown Expo 2026, taking place November 6th and 7th at Artifact Events in Chicago. With the event fast approaching, my fellow organizer, Kirby Allison, recently sat down with Ben Robinson, founder of Stitchdown and our partner in putting together what promises to be an incredible weekend for footwear enthusiasts.
Their conversation gives a great look into the history of both events, why we decided to join forces, and what attendees can expect from this year’s gathering. But more importantly, I think it highlights something that all of us involved in organizing these events have long believed: there is something very special about bringing people together who share a passion for quality footwear and craftsmanship.
For those who haven’t yet purchased their tickets, hopefully this conversation will give you another reason to come and join us!
👉Watch the long form video here:
How Stitchdown Began and the Importance of Community
One of the more interesting parts of the conversation is hearing Ben explain how Stitchdown originally came about.
Ben has spent much of his professional career in journalism and media, but has also been a lifelong footwear enthusiast. I, in fact, vividly remember sitting down with Ben when I first moved to NYC, enjoying some beers and a great chat with regard to the shoe industry and where it will be in the next 10 years. 10 years later, here we are joining forces!
In this interview, Ben humorously recounts how breaking his foot while wearing sneakers eventually led him toward better footwear, a pair of Red Wing boots, and ultimately the creation of Stitchdown.
What began as a media platform dedicated primarily to rugged boots and workwear gradually developed into a community of enthusiasts who wanted to do more than simply discuss footwear online.
Ben explains how one of their early meetups in New York brought together around 30 people, some of whom had actually flown in just to attend. That experience helped demonstrate the demand for in-person gatherings and eventually contributed to what became Stitchdown Boot Camp, now known as Stitchdown Expo.
Kirby touches on a similar experience from our Super Trunk Shows, emphasizing how important it is to meet the people behind the products rather than simply purchase something online.
Ben agrees, recalling his own visits to our New York and London Super Trunk Shows, where meeting shoemakers, examining their work in person, and having conversations with fellow enthusiasts made a lasting impression.
It’s something I have always appreciated about these events myself. You might come with the intention of looking at a particular pair of shoes, but before you know it, you have spent an hour talking to a shoemaker, learning about their craft, or discussing the finer points of leather with someone you have only ever known through Instagram.
These interactions are often what make the entire experience worthwhile.
Bringing the Worlds of Boots and Dress Shoes Together
Another interesting discussion revolves around the perceived differences between the two communities we are bringing together.
Kirby points out that, on the surface, someone who primarily wears Oxfords and someone who spends most of their time in rugged work boots might appear to be two completely different types of customers.
But are they really?
Ben makes the argument that the underlying appreciation is actually very similar. Whether you’re interested in a pair of handmade work boots or a finely crafted pair of bespoke Oxfords, the fundamentals are largely the same. You care about materials, construction, fit, craftsmanship, and the people who make the products.
As Ben puts it, “Great footwear is great footwear.”
I think this is one of the most important ideas behind our collaboration.
For years, the Super Trunk Show has focused primarily on the classic side of footwear, with an emphasis on dress shoes, bespoke shoemaking, tailoring, and shoe care. Meanwhile, Stitchdown has built an incredible community centered around handmade boots, workwear, leather, and the manufacturers behind those products.
Yet, there has always been overlap.
Many of the people attending our shows appreciate both worlds, even if their wardrobes lean more heavily in one direction. I saw many of my personal clients at last year’s Stitchdown and knew instantly that a joined collaboration would make for an unforgettable event.
Kirby also mentions his experience attending last year’s Stitchdown event in Chicago with me, where we were both pleasantly surprised to see attendees wearing everything from suits and dress shoes to denim and heavy-duty work boots.
And that is precisely what we hope to encourage this November. An opportunity for everyone to discover something they might not otherwise have explored.
More Than Just Buying Shoes
One of my favorite points from the interview comes when Kirby and Ben discuss what makes these gatherings fundamentally different from a traditional shopping experience.
Of course, there will be plenty of opportunities to purchase shoes, boots, clothing, and accessories. Many exhibitors will have products available to buy on the spot, while others will offer made-to-order or bespoke services.
But as Kirby explains, the real attraction is discovery.
You might arrive knowing exactly which brands you’re interested in, only to find yourself spending most of the afternoon examining the work of someone you’ve never heard of. You can easily spend 4-5 hours at the event and not even feel the time go by. That is what we love to create with these events.
Ben takes the discussion a step further by emphasizing the importance of actually trying footwear on.
We all know how difficult buying shoes online can be, particularly when dealing with unfamiliar lasts, sizing systems, and manufacturers. At an event like this, you can try on different sizes, feel the materials, compare constructions, and speak directly with the people responsible for designing and making the products.
Something that might take weeks of research online can often be understood in a matter of minutes when you have the actual product in front of you.
And for bespoke shoemakers, it’s an opportunity to have those initial conversations that may eventually lead to commissioning a pair of shoes.
There is no obligation to purchase anything. You can simply come, learn, explore, and enjoy being surrounded by people who share the same interests.
Personally, I think that is one of the greatest things about the Super Trunk Show, and I’m delighted that we are bringing it together with Stitchdown on an even larger scale.
What Can You Expect at the Chicago Super Trunk Show x Stitchdown Expo?
Naturally, the conversation eventually turns toward the actual event and everything that will be happening over the weekend.
Ben explains that while the two shows will be fully integrated, there will also be a dedicated Super Trunk Show section on the second floor of Artifact Events.
This is where attendees will find many of our classic footwear exhibitors, including brands such as Bridlen, alongside independent bespoke shoemakers, tailoring specialists, and other craftsmen.
Ben is particularly complimentary about Bridlen and the quality of footwear they offer for the price, which is always nice to hear!
Saphir Médaille d’Or, one of our presenting sponsors, will also have a major presence throughout the weekend.
There will be seven shoe-care masterclasses, covering subjects ranging from mirror shining to boot care, with opportunities for attendees to learn directly from experienced professionals.
As Ben explains, investing in quality footwear is one thing, but understanding how to maintain it properly is equally important.
The masterclasses are included with eligible event admission, although places are limited and advance registration is required. Ticket holders should watch for registration instructions, as priority access is given to certain ticket tiers.
You can find a more comprehensive breakdown of the participating brands and event details in my earlier article, Chicago Super Trunk Show x Stitchdown Expo 2026 – One Month to Go.
A Full Weekend of Events, Tours, and Experiences
One thing that Kirby and Ben repeatedly emphasize is that this is much more than a traditional two-day exhibition.
The activities actually begin on Thursday, November 5th, with special experiences for VIP ticket holders.
The Horween Leather Company factory tours have already sold out, but another experience that I am particularly looking forward to is the Optimo Hat Factory Tour.
Taking place Thursday afternoon, November 5th, this exclusive event provides an opportunity to visit Optimo’s remarkable Chicago factory and see firsthand how their beautiful hats are made.
It also includes a hands-on Saphir shoe-shining masterclass led by Preston Soto, followed by a cocktail reception hosted by Kirby Allison.
I’ve previously written an entire article about this experience, which you can read here: Optimo Hat Factory Tour – Chicago Super Trunk Show.
The Optimo Factory Tour Pass costs $225, plus applicable booking fees and tax, and includes admission benefits for the main Expo, early Saturday access, and entry to the Saturday evening VIP Wrap Party.
For those looking to make an entire weekend of it, this is certainly one of the more special ticket options.
Friday, November 6th, will also feature the HIDE materials trade show for industry professionals, followed by the main Expo opening to general admission at 2pm.
The show will continue through 9pm on Friday, with an evening market atmosphere, before returning on Saturday for another full day of exhibitions, demonstrations, and activities.
The Americas Championships of Shoe Shining
And, of course, we couldn’t have a Super Trunk Show without a shoe-shining championship!
Kirby discusses one of the events that has become a hallmark of our Super Trunk Show series: the shoe-shining competition.
This year, we are introducing the Americas Championships of Shoe Shining, presented by Saphir Médaille d’Or, with finalists competing for the title on Saturday, November 7th.
The final takes place from 3pm to 4pm, with competitors tasked with creating the finest mirror shine possible in just 20 minutes.
As Kirby explains, 20 minutes might sound like a reasonable amount of time, but anyone who has ever attempted a proper mirror shine will know just how challenging that really is.
Ben expresses his excitement about bringing the competition to Stitchdown Expo and allowing an entirely new audience to experience something that has long been an important part of our Super Trunk Shows.
It’s always an entertaining spectacle and something I encourage everyone attending to make time for.
Just 10 Days to Go – Will We See You in Chicago?
As the interview draws to a close, Kirby and Ben return to the subject that really connects everything they’ve discussed: the people.
One of Ben’s hopes is that attendees bring along friends who might not necessarily know much about this world of handcrafted footwear. I couldn’t agree more.
For those of us who have been involved in this industry for many years, it can sometimes be easy to forget just how unusual our little world is to the average person. Most people don’t spend their days thinking about shoe lasts, leather tanning, hand-welting, or the difference between a good mirror shine and a great one.
But once you begin to understand the people and processes behind these products, it’s difficult not to develop a greater appreciation for them.
That is ultimately what these events are about.
And with just 10 days remaining, I would love to see as many of you there as possible.
The Chicago Super Trunk Show x Stitchdown Expo takes place November 6th–7th, 2026, at Artifact Events, 4325 N. Ravenswood Avenue, Chicago.
General Admission tickets start at just $25 before fees and taxes and cover both days, with admission Friday from 2pm–9pm and Saturday from 11am–6pm. There are also Early Access and VIP ticket options for those wanting to experience more of the weekend.
You can purchase general admission tickets at the door if you decide to come at the last minute, but I would strongly recommend purchasing in advance. It makes entry easier and gives you time to look over the schedule and plan what you want to see.
GET YOUR CHICAGO SUPER TRUNK SHOW TICKETS HERE
If you haven’t already watched Kirby’s conversation with Ben, I encourage you to do so. It really gives you a sense of why we are so excited to bring these two events together.
And if you’re anywhere near Chicago, or have been considering making the journey, I hope this gives you that final bit of encouragement to join us.
Jesper, Kirby, Ben, and I will all be there, alongside an incredible collection of shoemakers, bootmakers, craftsmen, and enthusiasts.
Come say hello, try on some shoes, learn something new, and have a drink with us.
We look forward to seeing you in Chicago!
—Justin FitzPatrick, The Shoe Snob
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