Heritage Retail, Word-of-Mouth & Classic Craft with John Helmer III

John Helmer III, Owner of John Helmer Haberdasher

Explore how John Helmer Haberdasher, a small Portland clothing shop founded in 1921, has thrived for over a century and now sells to some 60 countries from a single 1,600-square-foot storefront. In this episode of the Wytpod, owner John Helmer III joins host Stephen Bland to unpack the story behind the business: how a classic haberdashery built on hats, custom suits, and hard-to-find accessories keeps finding new customers through word of mouth and online reviews, why he leans into being a “contrarian” retailer selling suits when few others do, and how being highly ranked on Reddit and Google has quietly plugged the shop into an AI-driven world of discovery.

“Interestingly, we’re selling more suits than we ever have. We’ve always been a bit of a contrarian business, you look out on the street and wonder who’s wearing a suit these days, but that’s a mainstay of what we do.”

John Helmer Haberdasher
John Helmer III, Owner of John Helmer Haberdasher

Hello, and welcome to our latest Wytpod. I’m Stephen Bland, your host with WytLabs. Today’s guest is John Helmer. John, feel free to introduce yourself and let our viewers know about your background.

You bet. I’m John Helmer III. I’m 70 years old, so I’ve been doing this a while. We have a small retail clothing store in downtown Portland that was started by my grandfather in 1921, 105 years ago. We’ve been in almost the same location the whole time, right on the corner of Broadway and Salmon in downtown Portland, and business has been pretty solid.

I bought the store from my dad more than 40 years ago, so I’ve been at it a while too. I feel like I’ll just keep going as long as I’m still having fun. My son, who’s in his mid-30s, is just moving back to Portland, and he’s coming back to work in the store again, as all three of my kids have in the past, so I’m hopeful this could work out for another generation.

We have a website, johnhelmer.com, and we joke that it’s world headquarters for us. We’re in a 1,600-square-foot retail location, but we sell to maybe 60 different countries around the world. Sometimes it’s only been one item, but we count it as international trade, on the World Wide Web.

Who is your target audience?

We’re a bit of a unique hybrid. Our name is John Helmer Haberdasher, which is an old-fashioned name. In England, a haberdasher is tailoring supplies, needles, thread, and linings. When it came to the United States, it evolved into men’s accessories, and that’s what my grandfather started with, ties, belts, tie clips, socks, and gloves. Over the years we’ve expanded on that.

Headwear is now about 40% of our business. We carry a few Western hats but no baseball caps, so it’s all classic, traditional fedoras and English driving caps. We try to buy from the US whenever we can, but we import a lot of European goods, so we’re kind of a classic winter wooly store, though in summer we sell a lot of classic Panamas too. Beyond headwear, we do a nice custom business, custom suits, shirts, and sport coats, and we carry Alden shoes, very fine handmade shoes made in the United States. And we’re still a haberdasher, with lots of hard-to-find accessories like suspenders and sock garters.
Many people come into our store and it’s almost like a museum to them, they’ll hang out for a couple of hours just looking at everything, a little amazed there’s still a store like this around. If we ever move a rack or a counter, some customers worry we’re going out of business, and we assure them no, business has been solid and we’re here to stay.

nterestingly, we’re selling more suits than we ever have, a lot of wedding suits and special-occasion suits. We’ve always been a bit of a contrarian business. You look out on the street and wonder who’s wearing a suit these days, and the big-box stores aren’t carrying them, so there aren’t many places to go, especially for something like a custom suit, where people want a more personal touch. You can order suits online and send in your measurements, and we do that sometimes for long-distance wedding orders, but a suit is very personal, and people appreciate the attention we give to make it fit right and help them pick the right fabrics, linings, and buttons.
As for our customer base, we skew toward male customers, but we get a lot of women too, we carry some ladies’ hats and do ladies’ custom work. The age group runs from the 30s up into the 70s and 80s, with the sweet spot around the 30s, 40s, and 50s. The nice thing about headwear is that it has a broad range, all age groups from kids to elderly gentlemen, men and women, across many socioeconomic groups. It’s almost like we have two stores, a headwear side and a clothing side.

How do your customers normally find you?

That’s a good question, and one we keep working on, because we need new customers. For a long time our customer base was aging, older men wearing hats, with younger men not wearing them as much, so we have to keep promoting ourselves. Word of mouth is very important, and we try to ask people as they come in, “Have you been in before? How’d you find us?” We’re finding that online reviews are big, especially Reddit recently, and Google. We rank right up at the top on Reddit, so that’s a form of word of mouth too.

Reddit is actually read by AI, one of the big aggregators pulls from Reddit to answer questions like “where can I find the best place to get a suit,” so it’s very important. Do you do any marketing with AI, or use AI in your business currently?

That’s a good question. I was going to say no, but now that you’re telling me Reddit uses AI, then yes, I’m using it more than I even know. My conscious use of AI is very small, mostly when I do an internet search and can tell the answer is AI-generated, or when I’m on the phone and it’s AI. Honestly, I wouldn’t even know what to do with AI for our business yet.

What are your best-selling products?

For a long time it was a European beret, a simple one-size-fits-all style. We’d sell thousands of them and advertise in The New Yorker and a lot of print publications, six, seven, eight of them, Smithsonian, Harper’s, and various art and museum magazines. Now we have another product called the Private Cap, made by Goran, and as far as we know we’re the only ones who carry it in the world. The company makes it just for us at a big minimum quantity and isn’t making it for anyone else, so we get a lot of international orders for it. It’s a specialty item, like a garrison or cadet cap, almost a small baseball cap.

What’s been the most successful marketing activity you’ve done? Most of our listeners are entrepreneurs with e-commerce brands, so what’s worked best for your brand?

For a long time, print ads really fueled our web business, but that’s dropped off, so we do very few print ads now. Anytime we do one, we make sure to add the digital edition too. Locally, we partner with some of the small newspapers and advertise in print plus all their digital options. We also have a mailing list, our local greater-Portland list has about 10,000 names, down from 20,000 over the years, and our national and worldwide list of past customers has maybe 60,000 names. We send out a little catalog, so we’re kind of old-school and analog, and I think people appreciate that, but we know we need to stay current too.

What’s an area of the customer journey you feel you haven’t cracked yet?

We’re trying hard to post more on Instagram. Our shipping guy does pretty well with it, but we’re only getting things out maybe once a month, so we know we can do a better job of keeping our name out there. We’re certainly not doing a great job there yet, and we could do better.

And you ship worldwide, so if someone comes to johnhelmer.com, you can ship anywhere?

Oh yes, definitely, worldwide.

Is there anything else you’d want our listeners to know about the business? We really appreciate you coming on.

I appreciate the invite. I think we’ve covered it, and people are welcome to contact me if they have any questions.

One hundred percent, John. We appreciate you coming on the Wytpod, and thank you for your time.

You bet, Stephen. Thank you very much.

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