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How style changed my confidence

How style changed my confidence

We all know style has the power to make you look good, but we’d argue its true secret power is its ability to make you feel more self-confident – something our stylist Toby Standing knows well from years of experimentation. He spoke with us about his journey to style confidence and why he thinks his personal journey might help inspire more confidence in the way you dress, too. Toby, we’re all ears. 

So it starts when I was maybe 11 or 12, and I watched MTV’s “Nirvana Unplugged” and saw Kurt Cobain wearing a shaggy mohair cardigan and some Chuck Taylor’s – it was like a lightning bolt of cool that set me on a path of trying to emulate that feeling, and what that path showed me was how I dressed would always reflect on how I felt internally. 

It’s easy to see clothes and the act of getting dressed as something frivolous, but I’ve always preferred to look at it as a form of self-care. In the same way wearing nice perfume or getting a haircut can give you a certain spring in your step, I think people often overlook the importance a sense of personal style can bring. So when I’m feeling particularly low or I’ve had a hectic, panic-filled morning, I put on an outfit I feel good in and the whole tone of my day will shift, and I know I’m not alone in that. How we feel changes how we’re perceived and what could be less frivolous than telegraphing who we are to those we come across. Surely that’s an intrinsic part of our personality? 

But, my confidence with clothing has been a real rollercoaster over the years. I remember a really early foray into personal expression, at age 13, when visiting Camden Market with my dad. I bought a waistcoat, red and black striped tie, and some vintage military cargos, and wore the trio with some black Converse. Not the best outfit looking back, but it was backed up with my dad’s encouragement and some (likely not overly sincere) compliments from his very cool friends. I wore the same outfit to a non-school uniform day (the highpoint of school fashion season), and felt out of place, so I never wore it again. I actually don’t remember if anyone even commented on it – I’m pretty sure it was all just internal. 

Then, when I moved to London at 18, I had a bit of a style renaissance. I was surrounded by the coolest people I’d ever met, and had more disposable income than ever before, so naturally, I was experimenting left, right, and centre. Some experiments paid off and have stuck to me to this day (looking at you, wide-leg trousers and Dr. Martens), but a lot fell by the wayside into a big pile of drop crotches, big fedoras, and super skinny jeans – I don’t think there’s anyone into style who hasn’t had a few cringeworthy moments. Whether it’s wearing a military coat four sizes too big, or a pair of patent Chelsea Boots you saw The Kinks wearing in a video from the ‘70s, these are all steps along the journey to true self-discovery (and for me, this is how I found my love for vintage). 

Throughout my school days and into my early 20s, I always considered myself as someone who wanted to be stylish and seen as ‘in the know’, but looking back, I think I was actually just lost. I jumped on a lot of trends, usually early on, so found myself having to psych myself up before leaving the house in something more daring than others might choose. I’m talking bright neon t-shirts, the chunkiest and ugliest sneakers you’ve ever seen, big emblazoned logos – all of which I jumped on because I saw them on style blogs and in magazines and thought that meant I was supposed to wear them (although they were definitely wearing me). In hindsight, I was wearing bold trends as a way of making up for a pretty severe lack of confidence.

Then, something unexpected happened – we all had to stay inside for months on end and the whole fashion machine I’d spent so long looking to for confidence and guidance kind of stopped. This came at a time where I was also putting effort into myself physically for the first time since my metabolism was at its peak in my teenage years, and was finally feeling like I looked like myself when I looked in the mirror. And suddenly, the styles I’d jumped on so quickly only months before felt like a costume, and felt so disconnected from who I was. 

I found myself watching that same MTV session that I’d watched all those years ago, and it had that same lightning-strike effect, accompanied by the epiphany that I spend so much time trying to help other people find their personal style but never allowed myself to actually follow my own North Star. All the people I look up to asstyle icons didn’t pay attention to what anyone else was doing; they were fully themselves and wore what they wanted to wear, what resonated with them and their interests. It seems so simple looking back, but I was chasing the wrong thing – I was trying to make other people think I was cool, instead of making myself think I was cool. 

So I started reevaluating what I was wearing and made the decision to ‘jump of the wheel’, as I’ve phrased it, to not play the game and to stop paying as much attention to what the capital F fashion world is doing and look for clothes that just resonate with me and what I enjoy. The kind of clothes Kurt was wearing, the kind of coats Patti Smith writes about, and the kind of stuff the brands I love (like Sweden’s Our Legacy, my biggest love) are drawing their inspiration from. My love of vintage has reached new heights, making up 90-95% of my wardrobe now, with the other 5-10% being made up of items from brands that I love, not the latest trending one. 

What I’ve learned is that being fashionable is sometimes more trouble than it’s worth, and that having a wardrobe made up of clothes that I really love makes me far happier than buying something that I’ll feel uncomfortable wearing in two month’s time. Embrace the journey, and find what resonates with you. Yes, style is subjective, but the only one you really need to convince that you’re cool, is you.


Words: Toby Standing
Illustration: Harry Tennant