In my last blog, I wrote about that moment when you realise your clothes belong to a previous version of you.

Since then, I’ve been playing around with what I’m wearing and how it feels. Some things still work but don’t feel ME now, so I’ve separated those out.

What I’m loving is more structure around the neckline, stronger shapes, texture… clothes with a presence.

Much more useful than standing in front of the wardrobe thinking, “I don’t like any of it.”

OK, Jane, I hear you say, that’s ok for you to do, but how do you move from knowing something feels wrong to understanding what feels right?

Start with something you love wearing:

Choose an outfit you feel great in. It doesn’t have to be dressy; it could be jeans and a hoodie (one of my faves!)

Firstly, how does it feel? Capture that moment so you know how you want to feel when you get dressed. I know I give myself a little nod in the mirror – it’s like there I am, check me out!

Then have a look at what you enjoy about it.

Perhaps the jacket gives you the structure, while the trousers let you move comfortably. Perhaps the neckline frames your face in a way you like. Perhaps there’s enough texture or detail to make it interesting without feeling fussy.

Try to get beyond “It’s flattering” or “It hides my tummy”. What do you like about the clothes themselves? And how do you feel wearing them?

That distinction matters. An outfit can meet all your usual criteria without giving you much pleasure.

And take a photo, sometimes referring back can help you see what the patterns are.

Turn a feeling into useful detail:

“This feels like me” is a good starting point. Understanding why gives you something you can use again.

For me, realising that I like structure around my neckline has been helpful. A funnel neck or a collared jumper offers something different from a shirt that, although perfectly wearable, no longer excites me.

If you enjoy an outfit because it feels relaxed, look more closely. Is it the soft fabric, the ease of movement or the way the pieces sit together? If it feels strong, is that coming from the shape, the colour or a substantial accessory?

You don’t need a whole new style vocabulary. You need a few observations that help you make your next choice.

Try one change:

Take an outfit you wear out of habit and change one element using what you’ve noticed.

If you enjoy texture, try a textured jacket. If you prefer a clear shape, swap a loose layer for one with more structure. If accessories make an outfit feel ‘you’, check them out before deciding the clothes are wrong.

Wear the result for part of the day. Notice whether you feel comfortable, whether you keep adjusting it and whether you would choose it again.

An experiment can be useful even when you decide you preferred the original.

Make room for different roles:

Some of my clothes still have a useful place in my working wardrobe, even though I wouldn’t choose them for every part of my life now.

You may have clothes that work for a particular role too. They don’t all need to express everything about you. But it helps to recognise the difference between choosing something for a purpose and wearing it because it’ll do.

As you learn what you enjoy, you can make more deliberate decisions about what to keep, how to wear it and what to buy next.

If you’re finding it difficult to answer that, my Identity Intensive 3-month style and identity coaching package gives us space to explore who you are now and how you want to express that through your style. Get in touch, and we can talk about whether it’s right for you.

Where identity leads, style follows.