Henry Holland, Those T-Shirts, & What Happened Next

"Do me daily, Christopher Bailey."
"Suck on my toe, Phoebe Philo."
While both designers may not have fashion houses to call home at the moment, the man who created the cheeky slogans, Henry Holland, is sitting pretty atop his own. A decade ago, the British designer made fashion fun again with House of Holland. The line was provocative, current (he can be credited with being the first to cast some of the industry's biggest models, like pal and then-flatmate Agyness Deyn and Behati Prinsloo), and, most of all, a colorful reflection of himself.
But after being dubbed the man to "save London high-street," what happened to those statement T-shirts? And where did the man behind fashion's football jerseys run off to? Well, he didn't go anywhere.
Following his viral success, Holland took some time to regroup and figure out just where he'd take his brand next. With no formal design training (he previously worked at teen magazines), he wished to take his label from a T-shirt company to a full-fledged ready-to-wear and lifestyle brand — similar to that of Tommy Hilfiger, he once told Vogue — but he was unsure of how to get there. His next idea was to rely on mega-brands with strong foundations that could support and compliment his visions, which resulted in collaborations with Umbro, Levi's, Le Specs, and more.
His latest venture, Ben Sherman x House of Holland, sees the unisex designer polishing his menswear skills on the London Fashion Week stage. Dubbed 'Heart & Soul,' the collection harnessed the essence of British style (svelte tailoring, patches, wool, an autumnal color palette). But he's still hard at work on his eponymous line, too, having just sent its fall 2018 offering down the runway last month. And he still makes those tees — only nowadays, like most slogan-splattered tops, they're more political than before.
Over coffee in Lower Manhattan, we caught up with Mr. Holland on his early days of fashion fame, life with Agyness, and how the industry hasn't actually changed all that much.
Photo: Rahman Hassani/SOPA Images/LightRocket/Getty Images.
House of Holland fall 2018
Photo: Catwalking/Getty Images.
Ben Sherman x House of Holland collection
So, after doing an entire men's collection, what’s the difference between menswear and womenswear?
Henry Holland: "Well, we launched at Fashion Week Men's but with us having such a strong womenswear background, making it unisex was a great way to honor our customer base. It’s 80:20 womenswear to menswear, so I think it was important for both brands to have the authenticity on both sides. With more and more emphasis on sportswear and streetwear, it's all very unisex anyway, and those are some of the elements that we wanted to inject into the collection. So, there's a lot more sportswear in there than maybe Ben [Sherman] would normally have in their collections.
"There's no real, true men's tailoring in there that can't be worn by a woman. The DNA of my brand has never been about tailoring or form fitting cuts. It's very much about a personality, an attitude, and a sense of humor, I suppose. I think those elements are very much easy to inject into pieces, whether it be from a design standpoint or otherwise. The thing I love about women is not telling them how to dress. They'll dress how they want to."
Well, you've always been that way.
HH: "Yeah, our T-shirts were shot on a woman but that's only because I lived with a female model. If I lived with a male model, I probably would have shot them on a boy, you know what I mean? I was cheap — still am — so, it's just the ethos of our company: We make stuff we think people want to wear, and then they can choose to buy into it — man, woman, or child.
"I think everyone is in a complete state of, like, How do we do show fashion? When do we show it? Do people want to go to 20 fashion shows in a day, in four different cities, around the world? Fashion is not dead. It’s like, Oh, so you're not gonna wear clothes anymore?"
What makes your shows different?
HH: "I think there’s an argument for why we continue to work on shows, and I think from the designer's standpoint it's about the romanticism behind presenting your work. If you don't have your own retail space, the only place you get to create the environment where you show your clothes is at your show, so you choose the music, the venue, the models. But that's your only opportunity to do that. I'm not a huge advocate for shows to remain; I think there are so many different ways you can showcase collections."
When it comes to the social media piece of it, how do you control that?
HH: "People are so protective of the collection, and I get it — that first look is the one reason why you gather those people in the room. Because if they've seen it before, and they're in their car on the way to the venue and there's like 95 backstage pictures, the feel and the prints — it's over. It removes the elements of shock and awe. But I much prefer posting before shows."
Photo: Karl Prouse/Catwalking/Getty Images.
House of Holland fall 2007
Let's shift gears a bit and talk a bit about the legacy and history of House of Holland. How did you come up all of the T-shirts, and now, why are you making them a little more political?
HH: "There's so much of what I did and so much of how I did it at the beginning that, in hindsight, was genius, but in reality, was complete cluelessness. So I think that's why it resonated and that's why it worked. I think people saw an authenticity to what I was doing because they just saw me as this kid that worked at, like, teen magazines and made T-shirts on the weekend, and was like, running around fashion shows trying to get in."
Did you ever get in trouble for any of them?
HH: "One."
Just one?
HH: "Only one. In all the time I did them, one person wrote me a cease and desist letter. It was a New Yorker."
That's so anti-New York, though.
HH: "I know! It's just something I wanted to wear and people I knew wanted to wear it, and it was just a bit of fun that resonated in the right way. It was the right time and place; it was a time when the fashion industry needed to show themselves to have a sense of humor. That's a very massive part of the industry now: We have a very open-door policy and social media means that people are much more aware of what designers personalities are, not just what their work is like."
There are certain tropes of designers, but you’ve stayed true to your brand.
HH: "Yeah, because the DNA of the brand is basically my personality, which means it's so much easier for me in that it’s just natural. I think both in my creative output (my clothing) and my marketing, it's very much an extension of my personality itself, so it' much easier than trying to be something you're not. To then turn that into a marketing proposition is exhausting. It's just like: I want to be me and if that works, great, if it doesn't, oh well."
So, what came after the shirts? There was a lull where we didn’t see much from you anymore.
HH: "I was trying to really affirm myself as a whole, ready-to-wear designer, I suppose. Since day one, I've always seen House of Holland as a brand. I didn't study design so that didn't sit very comfortably with me. So, I approached it as: I started a brand and that’s what I'm building. Those T-shirts went from zero to 100 so quickly. It was impossible to maintain that level of attention and global distribution. Especially when people were like, Oh, House of Holland, that’s a T-shirt brand, I was like, Okay, but here’s what else I can do."
Were people not really interested in that?
HH: "They were. It was in the UK; we still had great press and loads of attention. In the way that Agyness' career exploded, at the time, we were still barely making clothes."
Do you think she helped that exposure of that?
HH: "100%. It was crazy how synonymous those two things were. The week that I launched my T-shirts, she had her hair cut the day before we shot her in them. And she had it cut by some guy on her shoot and that was the shoot that launched the haircut. So, it was like, even though she had a hat on people were calling it the shoot that launched a thousand haircuts. But I was like, She’s wearing a hat. She took off at exactly the same time, and so it was like we were sort of synonymous with each other. I got a lot of attention globally from that, in a sense.
"I think the reason why it worked was that people could see that I hadn't hired her for a shoot and that it’d been more like, Let's go to a party. We lived in the same house for five years — we were just mates. There were a lot of things that people could see what was authentic about it."
Are you guys still good friends today?
HH: "Oh yeah. I talked to her not last night, but the night before."
So, designers are using T-shirts (again) to get a message out there. Is that kind of why you shifted to more political slogans?
HH: "As I've got older, I've become less able to not say something. There are also certain things that are happening in the world that you just have to talk about. I was so vocal about the Brexit thing because I just — I didn't get it. And we were asked so many times to do political T-shirts back in the day. But like, Katharine Hamnett? She can have it. I don't want it to seem like we did the same thing."
Was there ever a thing between you guys for having similar aesthetics?
HH: "We've never met. But I’m aware that she isn't my best friend."
Did you guys ever speak about that at all?
HH: "No. That's why I was quite definite in that decision. Ours were fun and playful — they were never meant to offend anyone. They were never meant to infringe upon anyone's thing. It was a conscious decision to try and do our own thing. And with the messaging behind them, it makes sense to become more politicized with them as I get older."
Why haven't you made a Trump one?
HH: "Because I don't even want to give him airtime. I don't even want to be seen to be profiting off his name either. I just don't want to engage. I mean, I'll engage to the point where I'll educate myself and be aware of it, but if I had a product with his name on it, it's just bringing his energy into my space, and like — no thank you. I’m not gonna stay silent and not do anything, but I think on the business side, I don't want to."
Photo: Karl Prouse/Catwalking/Getty Images.
House of Holland fall 2007
Photo: Karl Prouse/Catwalking/Getty Images.
House of Holland spring 2008
With the industry completely different than when you entered it, what’s happening now?
HH: "I’m a Gemini, so I love change. It’s what I thrive on. We've managed to keep a very compact team, so we're quite agile. We can change the way we do things very easily: we can launch menswear, we can launch different collections, we can work on different product categories, and we can do shows in a different way. I think we're supposed to be a creative industry, so we really need to be creative about it.
"There’s this misconception that fashion is this really young, vibrant, creative industry, when in fact, there are really large swathes of the industry that are run by old people who are set in their ways and are very focused on what's being performed. But I think it’s really started to shift now and people are starting to acknowledge that they are having to make changes. I'm very much happy to go with the flow."
We forget that just because all eyes aren't on someone or something that doesn't mean it’s not working.
HH: "Exactly. They're probably more successful because they're not spending all their money on making you look at them, to be honest. It's an exciting time. I'm so excited that I'm still doing it. Ten years! I just made some T-shirts as a joke, and I was like, Oh, I'm still here. I love what I do and I'm so excited to do it every day; it’s all part of the fun."
How happy are you right now in this moment?
HH: "Right now, in this moment? Probably an eight."

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