Can a pair of boots change the way you see yourself?
Sep 22, 2026Last Friday I caught up with a friend for coffee at her place. While we were chatting, she excitedly told me about a pair of boots a friend had given her. ‘They’re amazing, but I’m not sure if they’re me’, she said. I love nothing more than a wardrobe show and tell so I asked her to go and get them.
They were a pair of authentic goat and ostrich cowboy boots from Austin, Texas. Just crumpled enough to look fabulously worn in, not worn out. She put them on and enthusiastically walked around. ‘They're quite masculine, I’m not sure if they're me’. ‘Take them for a spin and see how you feel’, I suggested.
That night, I attended a 50th birthday party. During the course of the evening I was talking to some of my friend’s kids, all in their mid to late teens. The topic excitedly turned to shoes. They started talking about the latest shoes and showing each other photos on their phones. ‘What sneakers are kids wearing these days’, I asked. They told me. I remember the words Asics, gel and $300.
We are taught from an early age to dress for belonging. Follow the rules and you’ll be rewarded with entry to the group. Trends dictate what’s cool, if you follow the trends you’ll be cool. If you’re cool, you’ll be accepted. If you’re accepted you’ll be safe.
The need to signal belonging through our clothing and secure our safety doesn't end when we move out of our teen years. It continues on in adulthood as looking attractive, stylish, current, put-together, on-trend.
It is a drive that is exploited by the fashion industry through the trend cycle. There is always a new look, shape, colour, style, treatment, pill, potion or procedure to buy. The trend cycle is so fast moving that we barely even register it. We just hold on for dear life as the roller-coaster takes us where it wants us to go.
Which more often than not, is into a shopping cart.
So how do we understand what we want to wear when we have spent our lives having it dictated to us? Who are we without the signposts showing us the way? Do we want to wear Asics or cowboy boots? How do we know?
Two days after we caught up, I bumped into my friend on the street. She looked fabulous. It was a warm sunny Spring day and she was returning home from the farmer’s market. She oozed the kind of sensuous authenticity you simply cannot fake. ‘I’m wearing the boots!’ she proclaimed.
I hadn’t noticed.
I hadn’t noticed because everything she was wearing just looked like her. Her energy was magnetic because she was completely herself.
Turning away from the system in favour of self-expression can feel daunting. Stepping outside the rules we have been taught from an early age can feel like falling into the abyss.
But midlife asks us to step out anyway.
To stop looking for the signposts. To find our own way.
Self-expression is agency, it’s authority. It’s the ability to say, this is what I believe, this is what I value, and I choose to stand behind it.
It comes from trusting yourself enough to make your own decisions.
This week’s Embodied Style Practice
This week, when you get dressed, I want you to notice if any thoughts arise that sound like this:
Is this flattering?
Is this too much?
What will people think?
Does this make me look bigger?
Don't judge the thoughts, just gently notice them. Bringing awareness to your thoughts when you get dressed, helps you understand the difference between dressing for the rules and dressing for yourself. Awareness is the first important step when learning to dress from your own authority.
I loved talking to my friend’s teenage kids about the latest sneakers. It reminded me of my youth and how important it felt to fit in with the group, to wear the ‘right’ things and be seen in a certain way. I love being reminded of the experimentation that comes with being young.
But midlife carries with it a richness that youth has yet to earn. It is an opportunity for liberation from the rules. It’s the perfect time to get off the roller-coaster. It’s the perfect time to joyfully step into all that you are. It’s the perfect time to take the cowboy boots for a spin.
Julie x
Let's break some rules.
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