I Bought Four Pairs of Kmart Jeans and I Regret Nothing

Reinventing your wardrobe when your body, your life and your patience for bad fits have all changed at once.

I’ve been deep diving into personal style lately. My wardrobe needs a full reinvention.

A few things have converged at once. Since 2024, I’ve lost nearly a quarter of my body weight and intend to keep it off. My lifestyle has changed. My body shape has changed. And I’m at that very specific midlife crossroads of wanting to dress my age...

and also really not wanting to dress my age.

It started with conversations with close friends going through the same rebuild. We’re all navigating the same thing, figuring out how to dress the body and the life we actually have now, not the one from a decade ago. We’re not alone in this.

And for the record: wanting to look good is not vain. What you wear is a form of self-expression. It communicates something about how you feel about yourself, and that matters.

The practical problem, for me, is decision fatigue. I have a whole wardrobe of clothes, yet I consistently wear the same six things. Classic ADHD behaviour.

So the goal isn’t more clothes, it’s an intentional capsule built around the pieces I actually need, that works hard, reflects who I am, and takes the daily decision out of the equation.

Not the Zuckerberg “same outfit every day” approach, but close. Do the hard work now, reap the benefits for years.

This naturally sent me down a rabbit hole (hello, ADHD brain) that started with a colour palette session with Jade from Seasonal Stylist last year. Turns out we don’t just have a colour season, we also have a body type. And not the tired old apple/pear shape language that basically coaches you into hiding yourself or trying to look like something you’re not. More of the Kibbe method and essence typing working with your own body architecture and personality, rather than against them.

I am almost 50. I have been wearing activewear and Bali dresses for approximately one thousand years. It is time.

So I went shopping for jeans.

God. How traumatic.

I tried Ralph Lauren, cute, but couldn’t get the sizing right. I tried Levi’s, the sales assistant was wonderful, actually measured me properly, told me I have a long torso and shorter legs, and explained exactly why nothing was fitting. Great diagnosis. Still nothing fit.

They either weren’t high enough to hit my waist, or high enough but not wide enough for my thighs.

Then, on a complete whim, I tried on a pair of high-waisted wide-leg jeans at Kmart.

Perfect fit. Fits my waist and my thighs. I bought them in four colours.

I am now deep in research on body lines, architecture, and essence because this isn’t just about looking good (though, yes, also that).

It’s about having a framework so I can be truly intentional about every piece I bring in from here.

Also, can we talk about the fact that my true autumn palette is basically everywhere right now, the warm burgundies, olive and khaki, the deep earthy tones, the rich ochres. Finally. My moment. And once I have my blueprint properly mapped, the plan is to use it as a filter everywhere, including charity shops. Get the foundation right, and suddenly a $4 op shop find becomes a strategic acquisition rather than a mistake hanging in your wardrobe with the tags still on.

If only someone would just shop for me. I’m not a billionaire. So here we are.

Has anyone else gone down this rabbit hole? Tell me I’m not the only one who bought four pairs of something because they were such a great fit I had to get them in multiple colours…

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Funny how getting your wardrobe right and getting your life right require the same thing, intention. Knowing what you actually want. Stopping the default. That's the whole premise of Choose Yourself, my book on midlife recalibration. If any of this is landing for you, it might be worth a read.