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Dressing the Part: Samantha Harman On Why What You Wear Matters In Business

Samantha Harman is The Style Editor and helps founders create style strategies that get them known, seen and paid. Her work goes far beyond the typical stylist, doing your colours and choosing nice outfits; it’s about understanding how what you wear reflects and reinforces your beliefs about yourself and your business. We spoke to Samantha about the psychology of getting dressed, why so many business owners struggle with their wardrobes, and how to step into your founder identity through what you wear. 

Tell us what you do and who you work with. 

I help founders mostly create the style strategy that gets them known, seen and paid. A lot of people who start their own businesses are very good at one specific thing, their zone of genius. Then they realise when they start a business, wait, I’ve got to be the face of the business. I’ve got to learn how to market the business. I have to be visible all the time. I don’t know what to wear. And there’s a lot of underlying psychological stuff that comes with that. 

When you’re looking at your wardrobe, you’re not really looking at clothes. You’re looking at the physical manifestation of your beliefs, your hopes, your dreams, your identity, who you think you are and what you think you can do. If you aren’t bringing any conscious awareness to what you’re wearing, it is absolutely affecting your business. 

How does what you wear actually affect your business? 

If you get up in the morning and you put on the same pair of leggings you’ve been wearing for the last three years, and then wonder why your business isn’t developing, you realise, wait, I haven’t got any professional brand photography. I’m not doing video content. I’m not doing that podcast that I said I would launch. I haven’t started my YouTube channel. It’s because every time you put on those leggings, you’re confirming your belief that you are a little freelancer doing little freelancing. 

I help people step into their founder energy and stop telling themselves, “I’m just a little freelancer” or “I’m just this or that.” You’re a founder of a company. And if you don’t want to be sitting on Zoom when you’re 70 years old, you have to start thinking about yourself as the founder of a company and not someone who delivers services. 

What are the most common wardrobe mistakes you see? 

The thing is, when we’re like, “Oh, I hate my wardrobe, I hate everything in it,” what we realise when we zoom out is that we only wear a tiny percentage of what’s in it anyway. Our brains are always trying to make habits and patterns to make our lives easier. So we open our wardrobe, we literally centre in on the same five things on repeat, and then we just leave everything else, and we don’t wear any of it. 

Just chuck out anything you hate. That’s what I always say. It’s amazing to me how many people have stuff in their wardrobe they actually hate sometimes. “Oh, this is disgusting. I hate that. That’s awful.” Why are we holding on to this stuff? What are we holding on to when we’re holding onto these clothes? 

What about when people say they need to walk the dog or go to the gym, so they might as well just stay in leggings? 

When clients say this to me, what do you think I get them to do? I get them to get changed, and I time it. I literally time them. And it actually takes 30 seconds. It takes you 30 seconds to get changed. And people always say this to me, and I have a dog. I have to walk my dog every single day. Where are those things actually being used as a tool to keep you in your comfort zone? 

It’s less about the clothes and more about the things that you’re not doing, or the identity you’re confirming when you wear those clothes. And we make it such a big deal, like, “Oh my God, I have to get changed.” It literally takes 30 seconds. Sometimes I get changed like six times in a day. Just get dressed. There’s always a belief beneath the action that you’re taking or not taking. If you are saying, “Oh, but I need to walk the dog in a bit, or I need to go to the gym this afternoon,” what is the underlying belief behind the resistance to getting changed? Because there’s always something. 

What would you say to someone who thinks it’s selfish to spend money on clothes for themselves? 

I have so much to say on this one. This is explicitly used against women because, you know, patriarchy. And what it really links back to is the idea of female martyrdom, like women are supposed to exist for everyone else’s comfort and not have any enjoyment for themselves. But they’re also expected to exist in between these ideas that it’s selfish and silly for you to care about what you wear, but also, you’re going to be judged if you don’t care about what you wear. 

How can it be selfish to care about what you wear if what you wear makes you feel better and you have some sort of passion or purpose behind your business? How can it be selfish to do something that helps you get to the place that you want to go? Not enough good people are making money right now. The world is being run by people who do not care. It’s not selfish to want to feel good, make money, and then use that money for good things. That’s just a narrative that we’re told to keep the status quo as it is. 

 


 

Samantha’s book, Just Get Dressed: Why You Hate Your Wardrobe and What to Do About It, is scheduled for release at the end of January 2026. Her advice for the year ahead is simple: start with what you wear when you’re alone, when no one else can see you. That’s where the real work happens, and that’s what will change everything else in your business. 

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Sophie Cross

Sophie Cross is the Editor of Freelancer Magazine and a freelance writer and marketer at Thoughtfully.

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