Most of us have clothes in our wardrobe that we never wear but can’t quite let go of. I have a daffodil yellow tweed shift dress with buttons down the front that I bought about five years ago and have worn, I think, three times. Every time I open my wardrobe, it catches my eye and I feel bad. I feel guilty that I bought a dress that I didn’t need and don’t even really seem to like. But I also feel bad for the dress, because it really is very pretty, and what has it done to deserve being ghosted by me? That part sounds crazy, I know. But I try to be honest about the thought process of buying clothes and choosing what to wear, even when the truth makes no sense.

Like lots of us, I hate seeing stuff go to waste. I go to unnecessary lengths to make dinners using up whatever is in the fridge. I tell myself this is because it is healthier and more sustainable than takeout, but it’s also a kind of mental game to me, to use everything up. Odds and ends in the salad drawer unsettle me, like missing pieces in a jigsaw puzzle, and I have to find a place for them. Even if I suspect no one is going to be hounding me for my celery and beetroot risotto recipe, I find these dishes strangely satisfying.

I don’t want to give up on the yellow dress. I want to make it work, because not wearing it makes me doubt myself. Why did I buy it if I don’t want to wear it? If I don’t even know what I want to wear, what hope do I have of making good judgment calls on more important matters? And how can I make sure this doesn’t happen again?

So a while ago, I set myself a project, of wearing the clothes in my wardrobe that I hang on to but never actually wear. As well as the yellow dress, there’s a sky blue blazer in there giving me side-eye, a crimson silk skirt and a mustard coat. I’m a couple of months in now, and here is what I’ve learned.

Firstly: the key to finding your way back to clothes that you feel disconnected from is to try to relocate the spark that drew you to them in the first place. Take yourself back to what it was that you saw in the changing room mirror that prompted you to hand over your card.

This helped me with the yellow dress, because I realised that what it represented to me was getting dressed up – unnecessarily dressed up – for the kind of little outings I might do during the day at the weekend that could perfectly well be done in jeans and a jumper but would feel more of an occasion if dressed up for. I’m trying this, and you know what? That lady in the changing room, she was on to something. There is something oddly life-affirming about wearing a fancy pastel dress to go out and buy tomatoes.

Sometimes what you figure out is simply that you made a mistake. This is useful to know, because once you’ve faced that fact, you can stick it on the charity pile and move on. (Note to self: never, ever buy anything in an airport. Always a mistake, usually an expensive one.) But often, what the clothes you buy but don’t wear teach you is that over time your taste has changed, and your retail instincts haven’t quite caught up. You still reach automatically for pieces that feel as if they belong to someone familiar – but that person isn’t the current version of you. If this is happening, you need to bring your retail instincts up to date.

What this looks like for me is that as I get older I wear colour a lot less, but the magpie in me is still drawn to colourful clothes. I am going to be mindful of not shopping for the person I was 15 years ago. But in the meantime, I am interrogating my slide into beige and working on getting back in touch with my inner rainbow dresser.

At the very least, there is wisdom to be gleaned from the clothes that feel like mistakes. As the saying goes: sometimes you win, and sometimes you learn. Oh, and guess what I’m wearing today?

Model: Alejandra at Mrs Robinson. Hair and makeup: Sophie Higginson using Living Proof and Laura Mercier. Coat, £250, Leem. Dress, £29.99, Zara. Earrings, £190, Polène