Thomas Henry Made: A Suit For Every Man

5 THM Tom Caldwell - Designer Headshot (Hi Res)

Tom Caldwell is not your typical menswear designer. The Toronto Men’s Fashion Week Emerging Menswear Designer Award (EMDA) finalist didn’t go to fashion school. Originally, he was who his customer is today, a businessman who enjoyed dressing well, but could not find what he wanted on the market. This has turned out to be one of his biggest strengths.

Having tried just about every option out there and learning a lot along the way, Tom Caldwell decided to launch Thomas Henry Made. His suiting company takes pride in getting to know customers on a one-on-one basis before a single scrap of fabric is cut. In this #stmINTERVIEWED we chat with the modest Tom Caldwell about everything from his struggle to find the perfect suit, to how his family thought he was crazy to enter fashion and his number one grooming tip for men, which we strongly agree with!

Top Photo: Mauricio Calero

It was my love of menswear that got me into the business…

4 - 600 Mauricio Calero Thomas Henry MadePhoto: Mauricio Calero

STM – You seem different from other designers in that you tend to be a little camera shy in a sense and don’t make the brand all about yourself or your own personality. Why is that? 

Tom – Well, I’ve always been a very private person and I think I am unusual in that I’m not in fashion for the fame or personal accolades. I’m mean, that would great, but I want Thomas Henry to be more about the people that wear the suit and how they feel in it, rather than being about me. My satisfaction comes from putting someone in a killer suit and shirt combo that they really love, and seeing how satisfied and excited about it they are. It was my love of menswear that got me into the business, and I care about it enough I want to share and pass on that affection.

The upside is that I think it helps me stay focused on clients, and what it is they want – rather than making the product all about my tastes. I’m very open minded, and I think that is one of my strengths. On the downside, that makes me absolutely terrible at social media as I’m not one to put everything I do out there. I do what I can, but it’s certainly not a strength!

I can’t blame him since it did seem kind of crazy.

4 - 600 THMPhoto: Courtesy of Thomas Henry Made

STM – What excites you most about fashion in general?

Tom – Tough question. It’s hard to narrow, but I really like all the texture that you can get in a really great fabric, and how subtle details can really jazz it up. There’s a lot of combinations that can get lost on runway, but a contrast thread colour on a shirt or great real horn buttons or cool lining on a jacket are the sort of detail that makes you feel great wearing it (and isn’t showy at all). It’s how to make it your own, but without going overboard and making it obnoxiously obvious.

…it’s one of those things that still surprises me.

3 - 600  Mauricio Calero Thomas Henry MadePhoto: Mauricio Calero

STM – How did you decide to enter fashion given that you are a lawyer?

Tom – Kind of a long story, but it was quite a journey. When I first started out both in law school and at a firm, I always had the view that I never wanted to be a “suit”. Over time, and as I slowly tried out new things – in particular custom suiting, I really started enjoying wearing a suit to work every day.

That started a period of discovery and trying…a lot of stuff. Off-the-rack, made-to-measure, bespoke, high-end, low-end, you name it, I bought it. I kept looking for something that was the right mix of everything – great fit, good fabric, quality construction, an interesting experience with personable, no-pressure customer service and I never really found an option that was right on point. There are options sure, but nothing really stood out to me as a clear winner. So instead of continuing to search, I decided to offer the product and experience I thought was missing.

It’s all about having a conversation…

2 - 600 THMPhoto: Courtesy of Thomas Henry Made

STM – What was the reaction you received from friends and family when you told them you were going to launch a clothing line?

Tom – I still remember my Dad’s line: “You’re going to do what? Well, I don’t like that idea at all.” I can’t blame him since it did seem kind of crazy. But as I explained more about the idea to him, and he started to realize how much I had a real love for menswear and really understood the market, and now he sees how much I genuinely enjoy working with suiting, I think he’s slowly starting to come around.

…and you can’t do anything if you don’t nail that.

8 - 600 THM jason_lee2-fullPhoto: Courtesy of Thomas Henry Made

STM – What are some of the problems you noticed with other suits that you are trying to solve with your own line?

Tom – Firstly, fit. Fit is absolutely the most important thing with suiting, and you can’t do anything if you don’t nail that. We have great, tasteful cuts that are proper European silhouette – meaning it’s cut closer to the body, rather than being boxy or too slim fit.

Otherwise, even though there are a lot of other options out there to buy a suit, I found that there wasn’t really one go-to option for great fit, quality fabric, excellent construction and understanding, genuine customer service. And then add in the key point of finding all of that at the right price (no one likes to talk about pricing on luxury fashion, but it still matters at the end of the day).

To do it right, you’ve got to offer a great combination of fit, fabric and quality construction, and (while still trying to be humble about it…) I think I’ve managed to put together the total package. It took years, but putting it all together and offering a great product with my experience and understanding of the needs for men, I think it’s a deadly combination!

I don’t really believe in rules, except for one very minor point…

2 - 600  Mauricio Calero Thomas Henry MadePhoto: Mauricio Calero

STM – What was one of the unexpected challenges you faced while launching your brand?

Tom – Uh, well everything, and it’s incredible how much thought and effort goes into every single detail, and it is true that every little thing that matters. I would say the one thing that surprised me, or is a challenge, is how enthusiastic I get about the product but how long it takes to build a true brand name in fashion. I’m so excited with my product, and I feel like I’ve really done my homework on the market and have come up with a great product offering, and it is so obvious how great this would be for guys. But fashion people are a tough crowd, and they want to make sure you can tough it out in this business and pay your dues before they come around. I sort of expected that when I started out, it’s one of those things that still surprises me.

I want people to “do more you” rather than just coming to me to tell them what to do.

3 - 600 THM lc_tom1_056Photo: Courtesy of Thomas Henry Made

STM – For fall 2015, what is your favourite colour palette for men to wear?

Tom – I’m a big fan of forrest greens. It’s absolutely perfect for fall, and not a colour you want to wear any other time of the year. A nice chunky, forrest green tweed jacket always puts me in a great mood, and makes me appreciate a fall day.

I don’t believe there is any “one” menswear customer…

1 - 600 Mauricio Calero Thomas Henry MadePhoto: Mauricio Calero

STM – What are some of the typical questions you ask clients when you are getting to know them and understand their style needs?

Tom – Wearing a suit is so personal, so I really like to spend a lot of time getting to know someone, what they do, what they need and what they want before jumping right into anything. That’s all about genuinely getting to understand a client, and it has be personal and unique so I don’t have a real set list of questions I ask people.

It’s all about having a conversation, and learning as much as you can to be able to walk in their shoes (or suit…) and get what they want. While I think I have a great experience that I can draw upon from my career to help understand what men want, the goal is always about making sure someone gets exactly what it is they want.

And that’s really a key part of what I’m trying to do with Thomas Henry. So many times when I would buy for myself, it was clear the tailor/ sales guy already had an idea in his mind of who I was and what I needed, and didn’t listen to me and what I wanted. It was about pushing their idea of something, rather than help to bring forth my idea and personality. I want people to “do more you” rather than just coming to me to tell them what to do.

…It’s impossible to look good with that silhouette…

1 - 600 THM 6 thomas_henry2-fullPhoto: Courtesy of Thomas Henry Made

STM – Where did you get the idea to have characters? What role do they play?

Tom – The characters are my muses. They are meant to show the range and diversity of men that are interested in tailored clothing – since I think that really is the case. I say this all the time, but I don’t believe there is any “one” menswear customer, but I think a lot of the brands and retailers are stuck in this paradigm. Guys only want this, guys only want that – I don’t buy it. I think men’s tastes are really coming around, and they know what they want when they walk into a shop now and don’t need someone to do everything for them.

So the characters show a few different types of guys who love their suits. Custom suiting is all about personalization, and being able to show your personality through what you wear. The characters are a way to show the many different men that can still be a Thomas Henry man.They are also very real to me, since they are all based on different people I have known in my life so far – so see the real personality in them, and don’t see them just as characters.

600 richard_montgomery1-fullPhoto: Courtesy of Thomas Henry Made

STM – What is one style rule you personally never break?

Tom – Well I’ve broken them all in my time, and I don’t really believe in rules, except for one very minor point. Never the bottom button for your suit. It’s impossible to look good with that silhouette, and it’s a rule for a reason.

But other than that, there are no rules. (Other than formal wear. Always follow the rules on formal wear.)

STM – What is your number one grooming tip for men?

Tom – There’s nothing quite like a proper haircut. I think every guy would find themselves better off if they put the time and effort into finding a barber they like, who gives them a quality, flattering haircut, and then never leave him. The second most important relationship after your suit guy!

Make sure to follow @thomashenrymade on instagram, @thomashenrymade on twitter and check out to learn more. Looking to attend the TOM* EDMA show?  Visit to learn how.


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