What Were You Thinking? This New Fashion Podcast Has Us Hooked

If lockdown has had you mourning the most cherished items in your wardrobe – the bag that's always your plus one, the shoes that give you confidence when you need to stand taller, the party dress that accompanies you and your friends on every dance floor in the city – then designer Henry Holland's new podcast is the perfect aural antidote to the past four months of loungewear.

Launching today, What Were You Thinking? is the first podcast from former founder and creative director of House of Holland, and, boy, it does not disappoint. Featuring a line-up of sartorial stars including Beth Ditto, Eve, Alexa Chung, Gigi Goode and Paul Smith, his well-dressed celebrity guests take Holland on a journey through their life story via their wardrobes. Each episode glittering with hilarious anecdotes, moving experiences and wild tales all told through the most significant pieces in their closet.

Created in partnership with fashion resale platform Vestiaire Collective, the podcast encourages us to look back at the stories behind our clothes and cherish our pre-existing pieces as keepsakes imbued with memories. "I’ve spent the last 15 years working in the fashion industry, but I’ve been obsessed with the transformative power of fashion for way longer than that," Holland says. "Fashion’s so much more than what you wear to stop yourself getting arrested for public indecency. Every single one of us makes choices day in, day out about what we put on our backs and in turn how we want to be seen by the rest of the world. We’re going to explore some key fashion moments in my guest’s life: stories that have inspired or even informed their life’s direction, made a real impact, or just something that represents a time when they were deliriously happy."

Ahead of the launch of What Were You Thinking?, we turned the mic on Holland to talk Jon Snow's socks, Rihanna's sartorial power, and why you should never regret a bad outfit.

Pretty good to be honest - I’m not sure if we’re allowed to say that yet but I feel like the permission for pause that it has given me has really helped me. I’m competitive and a workaholic by nature, so the fact that everyone has taken a bit of a break has really helped me be ok with embracing that.

I’ve been decorating the spare room into an  office, working on the podcast and spending some time really thinking what I want to do next stepping down from House of Holland early March.

I love Elizabeth Day's How To Fail, she has such a diverse guest list that every episode I feel like I'm learning so much every time. I also love Amy Schumer Presents: 3 Girls 1 Keith as it is hilarious.

I wanted to chat with people that I think have a genuine love and connection to fashion and people that could offer different perspectives. We have designers, musicians and drag queens on there who all use fashion in such different ways. From image creation to align with their music, to creating fashion as their career and presenting as different characters, people harness the power of fashion in different ways and that forms the backdrop for some really fun story telling. 

So far I would have to say Alexa because we’ve known each other for nearly 20 years but have never sat down and talked about this subject matter so explicitly, so she surprised me the most in terms of how much I found out. It was really fun to talk as we were both so relaxed.

I used to have this turquoise tiger printed sleeveless top with punky patches all over it in the early 2000s. I wore that a LOT and on some of my most memorable nights out around that time. Probably at Sankeys Soap in Manchester! 

Anything with an elasticated waist! Not really - its funny, I still like to get dressed up and “dressed  for work” every day as my motivation to get on with stuff. My outfit helps me feel like I’m not doing nothing.

Shoes! I miss wearing all of my shoes as I’m so rarely outside  and when I am its just to take the dog for a walk and I don’t really have any need for any of the lovely shoes that I have in  my wardrobe.

It was about the year 2000 and I wore a grey funnel neck zip up shirt from Uth (it was an offshoot of Jigsaw Menswear and I was obsessed) a pair of grey linen trousers from Next and a pair of leather criss cross sandals. You know the ones - exactly like the ones David Beckham wore with a sarong.

What is the look from fashion history you'd most like to bring back? 

Pretty much everything by Stephen Sprouse - I love his work.

I think I’d like to just live in Bottega Veneta and that really would require money to be no object!

Not a single one. I always say that if you can never look back and think you looked outrageous or ridiculous then you weren’t trying hard enough!

Clueless, Empire Records and Euphoria. I referenced all of these in collections over the years.

Jon Snow. I just love his commitment to ties and socks. 

Daniel Lee at Bottega Veneta; he's creating a new look that is smartening the world up and showing us that we won’t be all dressed like overgrown teenagers in streetwear forever. 

Rihanna - always. She’s just inherently cool and so she never looks like she’s been dressed by anyone - even if she has. She’s experimental and doesn’t ever feel the need to play it safe. She loves fashion and it shows - she harnesses its power and acknowledges the playful, fun, humour and camp that we should all get on board with. She would be a dream podcast guest for sure!