Episode 160 40:40

Saying YES to Opportunities and Finding Creativity in Times of Adversity with Gemma Sheppard

What if your next opportunity does not arrive as part of a carefully mapped plan? Saying yes can open unexpected doors, but recognising which ones feel right requires a clear sense of who you are and what you want to create. This conversation explores the relationship between confidence, creativity and the willingness to move forward when life becomes difficult.

Dawn McGruer is joined by stylist and Smart Works ambassador Gemma Sheppard to discuss a career shaped by opportunity, from television and celebrity styling to creating her own newspaper and silk clothing collection. Gemma speaks candidly about finding a creative outlet after the sudden loss of her mother, while they also explore personal style, the confidence to start again and the importance of understanding your product’s purpose.

For female founders navigating growth, reinvention or the early stages of a new venture, this episode offers a thoughtful perspective on ambition alongside personal adversity. Listen to reconsider how you recognise opportunities, reconnect with your identity and bring greater clarity to what makes your business distinct.

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Episode Highlights

Jump to a moment.

  1. 02:16Fizz, fashion and finding purpose
  2. 09:28Dressing for confidence, not just the job
  3. 15:08Saying yes to the chaos of creativity
  4. 23:47Building a brand through grief and grit
  5. 31:57Silk, sambas and suitcase-friendly style
  6. 38:17Staying curious keeps you energised

Full Episode Transcript

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This transcript was created automatically and may contain small errors.

Hey, it's Dawn McGruer, the Business Growth Coach, and welcome to Dawn of a New Era, the podcast where we talk all things health, wealth and happiness, and where founders share the good, the bad and ugly of being an entrepreneur. Welcome to Dawn of a New Era podcast, and I am so pleased you're here. And we were just talking about how serendipity has kind of got here because I actually met you at a charity event that a friend of mine had invited me to, Fizz and Fashion. Yes.

What better combo? Fashion and fizz. I know, and also for Smart Works, which, amazing charity, and I did not know about the charity before that event. Oh, and it's incredible.

Honestly, very honoured to be an ambassador. Yeah, and I think the work is so special. So I want to first of all start with a little bit of the background on the charity. Yeah, absolutely.

Before we move into your world of entrepreneur. Well, I'd actually, you know, for me, the messaging behind Smart Works felt like it really related to everything I'd done on 10 years younger, and it really felt like something that has always been really at the forefront of anything I've ever talked about is when you look good, you feel good, and that equals confidence. It's like, it's just a mantra. It's part of, like, what I feel is everybody's USP.

And I think that nobody can underestimate that when you are found in a position, whether that's through maybe a separation or you've been made redundant or different circumstances in life, it can be incredibly intimidating for women to get back into the workplace. And I think it's become very apparent because not only for some people who have chosen to take time out, coming back into the workplace with the algorithm, doing your CV, you know, interview techniques, it can be so overwhelming. And so there was many aspects about Smart Works that I just loved. And then I felt like my voice could also help just raise the profile.

And it felt like I've got connections in the fashion world, and they do an amazing job. Job. And it's, you know, it's something that I also felt strongly about, is that this is a charity, but it's actually a service for everyone. And I think there is a lot of stigma in the UK about, I'm not a charity case.

That's not what this is about. And I really felt very honoured when they asked if I'd like to become an ambassador, because it was something I had been supporting and actively trying to raise awareness. I'd written an article for my paper and been talking openly on socials about it. And it just felt like such a natural next step.

And so I've really enjoyed embracing that. And it felt like everything I've ever done in my career has gone full circle, and it felt like it just made sense. Yeah, I love it. And I think one of the most powerful things when I was at the event was you and Michelle, and Michelle was on the podcast the other week, were chatting away, and the conversation was still the same with you as the host, as the ladies who were speaking.

And it was all about the confidence, the dress code, the societal stigmas, and dismantling some of that and really kind of elevating women back into a power situation. And I love what you say about the fact that it's not just a charity, it's for everyone, because there was a woman who spoke that day. Oh, it was amazing. Oh, and, you know, she'd gone and had, like, loads and loads of interviews, and that must be so soul-destroying.

And she went in and she had the stylist, and then she did the coaching, and then she went and smashed her next interview and got the job. And also, I think she also said, you know, sometimes having another set of eyes on you, we all think we've got our looks together, but sometimes somebody else just saying, How about we just try this? And as she said, that soul-destroying aspect at a time that you're already vulnerable, and you've got the fear factor. She'd got her daughter, she'd got bills to pay, and she was in a very vulnerable state.

I don't think anybody can underestimate. And I think that for me, she was an incredible spokesperson that day because also I think, again, she broke down complete stigmas and she was very honest. And I think that that is something that can be really empowering and also encourage other people to try the service because it's a service that's nationwide. And I think that for any brands that are listening to this, you know, old stock, it's such a wonderful way to keep fashion moving.

If you've got pieces in your wardrobe, we all have clearouts, it's a great service. And then on this kind of subside of that, they have a lot of incredible brands donate pieces that aren't necessarily for going to work. And then we host amazing auctions. We have incredible sales, which helps fund the centre.

So I can honestly say it's been a real revelation. And we've got the 10-year anniversary coming up. I'm sure you're going to be there. Absolutely.

And so I'm really looking forward to that. And I think tickets go on sale this week. Yeah, so that's great. Yeah.

I think one of the magical things with the charity is that obviously it ties in with what you do. Yeah. And, you know, I remember watching you on Tony O's Younger, and style and fashion has always been something that I was really passionate about. And I think women sometimes lose their identity.

Yeah. And a lot of the female founders I work with, they've come out of corporate, like the lady we saw at Smart Works. They've had babies, they've been out of careers for a time, and then they come back into work, and it's almost like refinding their purpose, but their identity. What's your advice for women in business and rediscovering their sort of identity in clothing?

Do you know, I think it's a really good question, and I think there's actually been a huge shift since pandemic. I think everybody's dressing differently now. You know, the days of me being in London suited and booted in very tailored suits, of course that still exists. It'd be wrong to say it doesn't.

But the nature of how we're dressing is much more eclectic. There's much more elasticated waistbands. I've just got some on today. I just think that comfort is still a factor, and that doesn't stop glamour.

You know, I think it's about a lot of people are still working from home part-time; there's a hybrid. So there's more desktop dressing. There's still this element, which is, I think that people are more conscious of their spend, and so they want to know that what they're purchasing is also going to work for their private lives, not just their work wardrobe. And I think that's the big shift.

In terms of advice, you know, the one thing I always say is that, you know, we all sit with plenty of clothes in our wardrobes, and I think we become a little bit that, Oh, I've got nothing to wear. The reality is we have. It's about being really organised about the wardrobe, and I am a massive fan of really putting things, when I'm with clients, whether they're celebrity or private clients, it's about organising the wardrobes, and I think that's a big factor because it really helps clarity and clarify what you need and what fits still, what you no longer wear. I'm a massive fan of Vinted.

I'm constantly getting my kids to sell things. In fact, these trousers are in my son's bag. I was like, No, I want them. So, you know, it's about making things work.

So I always say every, I mean every season, so I kind of split it into kind of the winter and the summer because I think, you know, here in the UK we do need a little bit of a hybrid. But, you know, at least twice a year I do a good clear out. I organise, and if you've not worn it, the reality is you're not going to. So get organised, put it into organiser, and I always work a week ahead.

So I look at my diary, I know what I've got coming up. I kind of play dress-up in my wardrobe. I enjoy creating outfits, and I think that way you actually, because you're hanging a complete outfit, you utilise so much more of your wardrobe, but you very quickly identify when you're missing something. And I think it's a great way to kind of be, you know, thoroughly across the whole capacity of capabilities within your wardrobe.

I love it because I've started only in recent years really trying to organise what I'm wearing in advance. Yeah. Whereas honestly, when I was working in London, I was getting about half four. I mean, like, I didn't even know what was in my bag.

No. Like, I was just packing, and I just felt like every suitcase was unpacked, repacked and everything. And the way that I feel now, I feel way more in control, but also I'm actually enjoying the dressing experience. Much more so.

And you end up being much more conscious about the complete look. So I go down as far as my underwear, and I have everything, my shoes, I have a run of rail just for the week ahead. And then I put it all back, whether it goes to dry cleaning or laundry or whatever, and then it goes back into the wardrobe. But this way, because you're always working, you're utilising the whole of your wardrobe.

And I think it's, as you say, you're empowered by it. It's massively time-saving, but you also enjoy it so much more. And when you think about your career, obviously, a lot of people will remember 10 Years Younger. I mean, it was an amazing program, and I think it really did open up a lot of the stigmas where people were prepared to actually kind of go and be critiqued over what they wanted because they wanted a new look and a new feel.

Yeah. So what was your career like? How did you even get into that? Every step of my career, I've never actually planned it, and I can wholeheartedly sit here and say I've just always walked through doors of opportunity.

You know, I think you make your opportunities and you make your luck, but at the same point, I'd never kind of set out with this kind of plan. But one of the producers of the show, I'd been offered another show with another channel, but it felt... When I went for the audition, it was slightly scripted, and I didn't like the fact that I was out of control with what I was going to say. And so it wasn't for me.

And then one of the producers, I'd done a TV show probably, I want to say ten years prior, and she had been—

One of the producers on that, and she rang me. She was like, Hey Gemma, do you remember me? Like, I'm doing a new TV show. It's a format.

We'd love you to be involved. And so I kind of went with a little bit of nervousness because I think when you're actually a stylist, there is that side that I was like, I want this to be a true reflection of who I am and how I am. And, you know, it was the first time in my career that I actually got trolled a little bit, which was really tough because I'm not in control of the edit. And there was lots that you didn't see on the show.

You know, you spend a large portion of time with people, and then it's edited down maybe to three to five minutes maximum. And post the show, I'd get these, like, scathing comments that were like... And then sometimes, I think as well, on occasions I did not agree, but within the format of the show, there was a lot of things to cover from, you know, the hair, the makeup, the cosmetic side, the fashion, also Cherry's kind of approach to being able to understand their backstory, and that's all got to be fitted in. And so there's only so much that can happen.

And so that felt quite harsh, even though there would be a sea of positivity. My mum would say to me, You know, Gemma, why does it... I would say, But it feels so harsh. And I wasn't afraid to, you know, very gently and politely reply and say, Hey, you know, in a world of hashtag be kind, I'm a human at the end of this.

I truly believe a lot of what we Was showing wasn't necessarily always shown. Also the context of what maybe they were looking for, i.e. we're going on a cruise, or I'm going to a wedding, or I'm, you know, wasn't necessarily always told.

So I think the premise of the show for me was that ultimately it was everybody's opportunity to set a new goal for themselves, a new line where you say, Tomorrow I'm starting a new life. Tomorrow's my second go at this. And sometimes the vulnerability behind the individuals was so intense that I think I felt so emotional about it because actually it gave people an opportunity to start over. And that for me is empowerment.

And that goes way beyond, and often what I would say to people is that goes beyond the meaning of fashion. What fashion means to you and what fashion means to me and the next person can be very different. There's no rights and wrongs. It's about an emotion that is how you feel.

And that for me was ultimately a show that really had a big heart, and it had great intent, and I wasn't given a script, and I really enjoyed the process, and it was really exciting. I think what it did for people out there, you know, in terms of just giving them permission to change, to try new things, I think, as you say, was very empowering. So tell us what happened after the show. What was the next step in your career?

All the way through the show, because the nature—I've always been on lots of projects all at once. I'm always spinning plates. It's just the nature of being self-employed and freelance, and I've had a crazy amount of opportunities, and I just— Believe in the power of yes. I love yes.

I am not a no girl. Where there's a will, there's a way. I'll make it happen, and I'm very good at that. So throughout all of this, I've always been doing and jumping on lots of different projects whilst even filming the show.

And I had a great opportunity that I was working with a U.S. label. I was traveling a lot, styling a lot of videos and commercials and different things, meanwhile looking after other TV shows and celebrity, and looking after also pop stars and music videos.

So I've always said it's a really colorful day in my life because I've always felt like no two days are ever the same. I can be here, there and everywhere, half the time living out of suitcases, juggling being a mum, juggling being a wife. You know, at the time we were living between Ibiza and a little bit in the UK, and so I would often be found at the airport. So I can relate.

I can relate. Yeah, but I've enjoyed it. I've really enjoyed it. I kind of like the chaos of it all, and I like the variedness.

So if you think about what you're working on at the moment, I remember you talking about your fashion brand, and I was really interested in the story because you covered some quite interesting points when you spoke about it wasn't easy, you know, and I think this is what people see. They know you from TV, radio, seeing you floating through life in their eyes and win, win, win success. You know, tell us a little bit about the journey in terms of getting that fashion brand and, you know, how that evolved. I think it's really important to say, you know, we do see the wins, but equally, I'm a real grafter.

Like, I work sometimes silly hours, and I guess only the closest people to me and even some of my friends will say, Gemma, you literally make my head spin. And I've never been afraid of hard work. I am very proud of the fact that I've always been a bit of a hustler, and even to this day, I still hustle. You know, if you want it, you've got to go and get it.

And so... In truth, and I'm going to say this quite quickly because I don't want to get too emotional, I lost my mum very suddenly, and it was very challenging. So the paper was born out of my way of coping. It was my coping strategy for a time that felt challenging in a way that I didn't see coming.

Sorry. And I felt like I had to use my sleeplessness and my lack of sleep to sort of channel my creativity. It was the only way I kind of knew how to cope in the middle of the night where, let's be honest, the middle of the night is really lonely and it feels long. And I could get to sleep, but I would wake up with this awful weight, this awful PTSD, if I'm really honest.

And, you know, it was such a shock to me. I was with her one day and she was gone the next. And she was my biggest cheerleader. She was my best friend.

I'm an only child, and it just felt like my world had just suddenly ended in a different way. Although I've got this beautiful family of my own and beautiful children and a wonderful husband, this, you know, wonderful woman in my life was gone. And I'd been more prepared with my dad because he'd been ill for four years prior to him dying, four years prior to my mum, and I just didn't see it coming. And so that strength of your mentality to just keep one step going, and then also in my job being a people pleaser and a giver and, you know, the empowerment to somebody else at a time that you're quite vulnerable yourself.

But you—I'm the ultimate professional, so I don't want to show that. It just meant that I just needed to not sit. And be, woe is me. I had to put myself into something, and I'd always loved newspaper print for lots of reasons.

And it kind of started partly because I was writing a lot for different publications. I'd always have journalists ask me to quote, and then it would say, Shepherd Style says. But I'd written quite a lot, and I thought maybe I need to house my own content. I was traveling the world.

I was doing amazing things. Why don't I look at how I can talk about the things I really love? So whether that be my makeup, whether that be my perfume, whether that be the latest—you know, I'm not somebody who's very trend-driven. I've got wardrobes and clothes that I've had for years, but I can still talk about them and say, Get the look, and just try and inspire other women in a world of my world whilst being on the hoof.

And when I'm at the airport, I can utilize my time. So it all started with the newspaper being my—literally my salvation, and not feeling like I spent four hours in the night wide awake. You know, I'd wake at usually around one, and I'd stay up till around five, and then I'd go back to bed, and then my alarm would go off at 6:30. So I was falling asleep, sleeping, waking up at one, working till, you know, five, and then going back to bed for an hour and a half, up with the kids.

And so it started with that, and I was on the beach in Ibiza, and I was like, I love the word voyages because of my travels. I wanted it to feel retro. I loved the idea of the vanity side of my life. So I saw them as like these two kind of voyages.

She travels the world, vanity. She's going to talk about her makeup bag, and she's going to talk. So it was these two worlds, and I've always loved cooking. Please know I'm not a chef.

I'm not a makeup artist, but these are things that are in my life. And I was like, I can empower and talk about other wonderful people who are brilliant cooks, and then I can interview them, and then we can sit and make a dish together, and then we can talk about what's in your pantry and what are your top ten items, and when I'm traveling, what should I have with me? And then I can reference clients like Davinia Taylor and why her brand has really impacted my life. And it just felt like I was using this negative time with joy and creativity, and I guess.

That was just really wholesome, and it just meant that I felt connected. And through that, I'd always talked about my love of silk. I've always loved silk. I think it's an amazing natural fibre, and it keeps you cool in the summer, and it'll keep you warm in the winter, and you just layer it up.

And I was like, I want to create something that also felt glamorous, effortless, but also had the comfort factor.

Exactly what we're talking about, like cool palazzos with elasticated waist, but you can dress it up, you can dress it down. You've got this kind of versatility, and I wanted to keep it quite capsule, but everything I was ever going to drop within it would keep adding to the next thing. And actually, as I've gone along, I've almost refined that even more, because I love the fact that when I wear it, I'm never going to bump into somebody in it. It would be really unlikely, even though the Mexico, which is the leopard, has been, like, ridiculously...

I think my mum was wearing that. She was. She looked amazing. She looks incredible, and she looks so good in it.

But do you know what? I could see that outfit on so many different age ranges. Oh yeah, that's the beauty. That's what was so fascinating about the range.

And, you know, like when you were designing, like, who was in your mind's eye? I've always loved old school glamour. I love glamour. Even now, like when I look at anything, I always bring it back to glamour.

One, because I think there is something so magical about the empowerment of glamour. But I wanted it to be exactly that. I wanted my daughter to be able to wear it in a different way to the way I wear it, but my mother-in-law to be able to wear it, and they both do. And so my daughter, who's now 18, 17 at the time I launched it, and it's only just a year old, the brand.

My mother-in-law is, you know, a little bit older. She's in her early 70s. But how amazing that we've all got a collection that we all wear so differently. You know, Tallulah will wear the Mexico with her, you know, Sambas, and sometimes she puts it with a heel boot.

She might tuck them in. She'll use the scarf as a, you know, a bandeau, or she'll tie it in. Like, it just gives so much versatility. And what I love is I can literally pack 30 outfits in hand luggage, because silk packs to nothing.

Yeah. So I can pack it with tissue. I always wrap with tissue. I can take hand luggage, and I've got so many clothes with me.

And this all kind of, it's always been a bit of a joke because back in the day when I worked with... I worked with Blue. Duncan once said to me, You know, Gemma, have you got so many outfits? And I was like, Oh darling, I just pack silk.

So he always teased me for it. But I've always loved silk. And so now, as part of the next drop, I've done limited editions. And so they're really beautiful.

I've done a slightly more like a caftan-style one-size jacket that's just heaven. I've done a different style, almost like what I call a grandad pajama shirt that's got no buttons. It's kind of, again, amazing sleeves. But if you've already bought several pieces, it's going to go with all of them because this one's got a print.

And I've always loved colour. And so it's just been very experimental. And again, it was all born out of me keeping sane in the middle of the night. I mean, your journey has been very organic.

It's been driven by, as you say, possibilities and opportunities. I love what you say about saying yes. I'm definitely a yes person. And I always think if I can push myself out of the comfort zone, that's the excitement and that's the joy.

And even doing the craziest things, like when you think, Well, could I do it tomorrow? Could I fly to this place? Yes, I can, you know, and seizing the opportunities. If you were to give advice to founders who are thinking about, you know, clothing brands, or it could be products, or just launching their business, what would be that sort of number one thing that you think would really help them stay strong when it's tough in those early days?

I think it's about really understanding what your goal is. And for me, mine was very much driven about the fact that I travel a lot. I want to look good when traveling. I want comfort, almost like wearing silk pajamas, but I also want to still look great.

And when I get off the other end, if I switch out the shoe, I'm ready to go. Because often, if I'm landing in America, the whole concept of going back to the hotel room is, as you know, dangerous because you're going to fall asleep. So you've got to keep going. And therefore, I think it's important to understand your USP.

What is it? What is the big picture? Even if you don't know fully the big picture. Is it that you want to start with a T-shirt design?

Is it, you know, and often it has to start from a place of passion, and you have to understand what is it, what do you think is missing in the market, or what have you seen that you love and you buy all the time? There's going to be somebody else. And I think the one thing now that has been revolutionary for so many people in pandemic is, you know, everything can be done online, everything can be done through Instagram, everything can be done through Shopify. You don't need this big machine.

The thing that I think is challenging is MOQs, you know, because a lot of factories don't want to be producing small quantity, and I think that's a really important fact to really take on board. And I think quality is at the forefront, and, you know, navigating that is really important. But because also you've got to look at your margins and what— so I always say small steps for the bigger picture is always really empowering. And obviously you've had such a varied lifestyle, you know, and you could probably tell stories all day long.

What's kind of the pinnacle moment where kind of like you knew in your career, like your heart of hearts, because you're a very passionate-led, that you'd made it, like you'd hit the point where, like, it's happening? Oh, I don't know. Do you know, I don't know that I've ever thought that. I think I always take a moment to look at what's going on.

So there is no doubt, I very much remember my very first X Factor final. You know, it's live from Wembley, it's chaotic, it's madness, and things are changing. And I remember saying to the team, let's just step outside of, like, because you're set up literally in a car park in Winnebagos, let's just take a moment. We are streaming live, and at that time to millions of people, and that for me...

It was a moment of, wow, this is really exciting. Many people—this is a moment of history. It's a moment of TV history. We're creating the looks that are being streamed to lots of people, and we are watching this as it happens.

It's live. And just to take a moment where you can hear the hullabaloo, you know, you've got the warm-up artists, you've got everybody cheering. There's this incredible energy, and you're about to create live television, is really exciting. I think I've always loved live TV.

I love the energy of it. But as I said, if I sit here and say, what moments kind of define that, I don't know that I've ever thought that, because I guess I've always had in my mind things that I'm looking forward to. And not that I always know necessarily what's coming next, but I always have like an outline of people I want to work with, or territories I want to work in, or projects I'd love to be a part of, and navigating that sometimes. I do believe has to be slightly organic.

You can't force it. And I think sometimes you just have to go with that process and understand the industry is changing, and there's a lot of young people, very talented. And I've always been a massive fan of surrounding myself with a mix of age groups. I think I can learn from you, you can learn from me.

Somebody coming in at 18 to 20 can teach us something, and vice versa, we can share something. And that's what I do love about collaboration, what I do love about being physical in the workplace over working from home. I think there's a lot to be said about that. So I'm always in this kind of moment of, if I'm in a creative space, I'm happy.

Yeah, I love it. And I think it's really important because I love the dynamicness. I love that, you know, I can be speaking to somebody who is in their 20s starting a business, and I can share insights of when I started my, you know, first business at 21. But as you say, everything's changed.

Yeah. And like how we grew up was very different to how people are growing up now. And I think that the fact that if we're dynamic in the approach and we can take on board other age ranges, actually, I think that facilitates business and creativity way more. Massively.

So, is there a book or a podcast or a person that's been influential to your journey that you remember? I think I've been inspired by many people, including clients. I really do. I think the energy on set, the way people behave really matters to me.

I think what you put in is what you get out. I always treat people how I wish to be treated. I massively believe that there's a wonderful empowerment through an energy. I massively believe in good energy.

I think great places come from that. And I think there's something really exciting about bouncing ideas from people. You know, in terms of the industry and reading books or podcasts, there's many things that I dip in and out of. You know, I've been reading recently.

Let Them, which I've been loving. And actually, often with books, I have them as audible because I'm always in the car doing long journeys. And there's something also about the author reading the book to you that I think gives you a different intention to you reading it yourself. You hear it in the spoken voice, and I think that is really empowering.

I also love Brené Brown. I love a lot of kind of what I call the American sort of empowerment coaches. Yeah, the personal development. Yeah, because I think we all have capacity for development.

And I think that I genuinely and truly believe that every step of our journey will take us to our next place, whatever that looks like. And as long as you've got this kind of willingness and ability to be, I guess, open, the signs are there sometimes. And I don't say that from a place of anything other than I think you just have to trust the journey. And as long as you're willing to put in, you will get out.

And that's where, you know, if you're starting out a new business, it's about the determination.

It's about showing up. And for me, it's about consistency. Ultimately, everything comes down to consistency. If you want something, you've just got to keep, keep going and do it with consistency.

And I think the way of looking at challenges, I always think that, you know, sometimes we keep pushing, and sometimes we're being offered a different trajectory. And that if it sometimes feels that it's not aligned to your gut, I often feel like it just wasn't meant to be and move on. And often it puts us in a different path. So, as you know, in my podcast, I always like to cover the epic journey that everyone's gone through, but we all love an embarrassing story.

So, would you be so kind to share your embarrassing story with us? So, I actually do have a good one. I was thinking about this this morning because actually I've just been organising my cupboards, and I stumbled across a pair of boots. I was going to Canada to shoot a music video, and it was, you know, it was full of snow where we were going, and they'd created—it's actually in a natural park—and it creates like a beautiful ice rink between the trees, and then it's got like festoon lighting.

And I'd seen all the images on Instagram. I was like, Oh my God, it looks amazing. So I'd planned all my outfits, and when I got to the airport, there was this amazing pair of Chanel snow boots, and I thought, Oh, they're so fabulous. Of course, if I wear those, nobody wants to be in snow boots.

I want to wear those snow boots. So I'd got this amazing long black coat. I was like, These boots are like... So I buy them at the airport.

I even say to them, Keep the box. I mean, what was I thinking? But I just didn't have space, so popped them on. And I arrive in Canada, first day on set, and everybody's like, Oh my God, I love your boots.

I get off the Winnebago and I literally—like this—because of course they're polished plastic. They were like patent. They look like patent leather. They're polished plastic, and whilst they were like a chunky boot, they were smooth as anything and so shiny.

And I ended up having to send a runner to get me a pair of really ugly Merrells. So it completely went wrong. So that was my fashion faux pas. Did you hurt yourself?

No, I landed. I mean, listen, I got up quickly. I landed on my bum. I've got plenty of padding.

I was all right. But it was just the, you know, the mortification. So they've actually sat on a shelf ever since. They're still in perfect condition.

They're the most unpractical shoes. They should have come with a health warning. We all love impractical shoes. I mean, there's so many times that I have had epic disasters just by wearing heels.

And we were talking about this before. We still love a pair of heels. You know, I know so many people now who just wear flats. Yeah.

And I just think that there has always been something for me. When I put my heels on, I just feel different. Yeah. And know it wrecks your feet.

You stand different. You stand tall. You stand... I love a heel.

Listen, I'm all about the heel. I mean, I speak on stages for like, you know, two to three hours at a time, and people are like, How are you still standing in your heels? But do you not think that's adrenaline? Yeah, of course it is.

You feel empowered in that moment. And I definitely think, you know, people say to me, How do you do it? I just do. And I feel better for it.

Yeah. And I think you just go with what you're comfortable with. If you want to wear your flats, you wear your flats. If you want to wear your heels.

But for me, I think heels will always be a part, and I don't go on any trip without coming back with shoes. Oh, the girl after my own. Well, I've just, you know, I fell in love with sneakers, and I know they're a bit controversial. Some people love them, some people hate them, but I feel like there is a time and a place for them.

They're like the hybrid, you know, the comfy shoe. So tell us then what is in store for you sort of over the coming year and what you've got planned. Well, obviously the range I'm expanding. I've actually, I'm going to be taking it into the UAE, which is really exciting because I'm going to be doing headscarves with it.

And I think that's really beautiful for me, that I'm actually able to take my collection and develop it in different ways. I still love it's USP, and I'm really enjoying creating. I've got a really loyal clientele base, and so creating now pieces that feels like they're getting unique pieces is really lovely. I'm starting a new project, which is a little bit too early to talk about.

And then actually, I've started to map out my book, which I think is something that It's quite exciting. It's a mix of stories and my career, my clients, you know, and these amazing opportunities I've had, but also peppered with, I think, really practical tips. Because I'm not somebody who just goes out and shops, you know, and I also love high-low fashion. I do love the Great British High Street.

I do love designer pieces. But when I buy, I buy with real intent, and I've become really good at it. So I've got lots of kind of what I call, I think, just helpful tips. I don't really believe in do's and don'ts because I think everybody has to have experimentation is part of also identifying who you are, and that's okay.

So I like to let people have space to develop their own sense of style. I think that's a really important part of everybody's journey. It doesn't stop us from guiding each other. I think one of the things that I always remember, and this has been a staple through all of my life, every time I go somewhere, I always dress how I want.

I don't really dress necessarily for the situation, and I don't know if that's a good thing or a bad thing, but people always used to say to me, Dawn, oh, you always look glamorous, but it was always kind of said in a, You're dressed too much. But it almost kind of made me go the opposite direction, where now I'm like, if I want to go and wear to the local pub a bright pink, fancy, glittery dress, I will. And I think the thing is, is we shouldn't be frightened of expressing ourselves. No.

So what's your favourite sort of high street fashion at the moment? Is there anything that you're seeing that is evolving? Because I know, like, a lot of the brands like Marks and Spencer's, I mean, they seem to be very diverse in what they're offering now. Yeah, and I actually really love tailoring.

When I say tailoring, I kind of like soft tailoring. I like to mix and match. I love great jeans. I love denim.

I think there's some really great pieces out there at the moment. I think River Island are doing some incredible things right now. I'm also a big fan of Zara. I like the fact that if I am somewhere, and the one thing, because I travel a lot, I have lost suitcases in the past, I keep the designer pieces or the key pieces in my hand luggage, and then I do travel a lot with Zara.

But I'm also very good at, you know, I find a great Zara piece, sometimes I'm like, I want to switch out the buttons, and I've got my mum's lovely button tin, and she's got a really big button tin, but I also buy vintage buttons a lot. I love that vintage flea market, and I also have, you know, some of my grandmother's clothes still. So I quite like this whole thing of I might have a great pair of jeans. I love River Island for their jeans.

I love Zara for their jeans. I think M&S have really come back with some vengeance. I loved it when they, you know, relaunched different brands. But I think we are really lucky with the high street, and I think that I've always been a big fan of being able to feel clothes.

So I guess everything going online is something that I love it when there's a video attached to it, whether that's on Net-a-Porter or somewhere else, because it does really help. But I also really love digging back into my wardrobe and kind of revamping. What I've already got. I love that.

I think I'm good at that, and I think that I utilise my wardrobe really well. And I'm also not—I'm good at letting it go as well. I'm good at moving it on. And I think that feels, as long as it goes for a second life, I'm always happy.

I know, I've just had a big clear-out, so... And it feels good. It does. It feels very cathartic, very empowering.

And then during lockdown, I found Wolf & Badger. Okay, I love Wolf & Badger. Oh my goodness. I, like, literally every week I have to buy something from it.

They're great. Yeah, but up-and-coming designers. Yeah, and that was the thing that I loved. You know, they couldn't get their designs out there.

No. And then they went onto this huge forum that gave them a massive audience. Yeah. And, you know, every time I'm going to a wedding, you know, I get a dress from there, and I know that no one else has got it.

And it's slightly quirky. It's different. Yeah. And have you been to the store in Coal Drops Yard?

No. It's fabulous. You must go. It's really good.

I mean, I worked with Wolf & Badger back in the day when they were in Notting Hill, and they were much smaller then, actually. But what a great opportunity for up-and-coming designers. And, you know, I think as well, young companies, when we're talking about, you know, which way to go, there's all these things. And I think that, you know, it's affordable luxury fashion or designer fashion, and I think it's really well done and really beautifully curated.

Yeah, it's one of my favourites. So, thank you for coming on the podcast. Pleasure. Thank you for having me.

And I want people to know, obviously, how to find you. Where's your favourite socials? How can they find out about your fashion brand? So, my, you know, it's really me.

It's @ShepherdStyle. I don't think I'm a particularly good social influencer, but I put it out. My papers under voyage is in Vanity, but everything comes through ShepherdStyle, and actually my Facebook and everything is all linked to my Instagram. I'm trying to get good at TikTok, much to my daughter's horror.

You know, early days and all that. Yeah, but the thing is, it's all an evolution, and, you know, I'm still not really TikTok. It's curiosity for me. I just like to understand it.

Yeah, I'm very late to the party, and it's a different platform. It's a different way. It's a different way of doing things. But actually, I like to understand.

I think if you stay curious, you stay really energized. And I think curiosity is the greatest gift of all. Oh, that's an amazing parting gift for everyone. Thank you.

So thank you again. Pleasure. And yeah, have an amazing week, and I can't wait to see what's coming. Also, hopefully we're going to be doing a joint event for artwork.

I know. That's going to be so exciting. So that's another exciting... Confidence confidential.

Absolutely. All right. Thank you so much.

Thank you. Thanks for listening to Dawn of a New Era, the podcast brought to you in association with the Her Power Community. This initiative was founded by myself, and it's all about empowering female founders to recognize their limitless potential and pursue their ambitions with confidence. Now, there is less than 1.

8% that goes into investing in female-founded businesses, and we are here to make positive change. So come and support us on Instagram at Her Power Community and find out more about what we're doing to support female founders to scale and grow their businesses.

About The Billionaire Brain® Podcast

The Billionaire Brain® Podcast with Dawn McGruer, formerly Dawn of a New Era, explores the psychology, neuroscience and behaviours behind extraordinary success in business, wealth and life.

Through solo insights and conversations with founders, investors, millionaires, billionaires, authors and experts, Dawn explores how identity, thinking and behaviour shape what we create. New episodes are released regularly on Apple Podcasts, Spotify and YouTube.

  • Episode · 160
  • Published · 12 June 2025
  • Run time · 40:40
  • Host · Dawn McGruer

About Your Host

Dawn McGruer is an entrepreneur, 5× founder, award-winning keynote speaker and Forbes Books author of The Billionaire Brain®.

With more than 25 years in entrepreneurship, Dawn's work explores the intersection of founder psychology, neuroscience, wealth, identity and business growth.