From Overthinking to Action

When it comes to personal style, it’s surprisingly easy to stay stuck in your head. That’s why something style and mindset coach Kristen Caine says has really stayed with me: our thoughts and feelings are behind our style struggles.

When she works with clients on their wardrobes, she doesn’t just focus on the clothes themselves. She looks at the thinking behind them—the beliefs, the assumptions, and the stories people are carrying. I love that approach. It makes complete sense to me, and I find myself saying a quiet “amen” every time I hear it.

However… I’ve noticed something about myself: it’s very easy for me to stay in my head.

I can think about style. Reflect on it. Analyze what might be getting in the way. I can even identify beliefs that may not be serving me. Yet, when it comes time to actually do something—to engage, experiment, and just do it—I feel a kind of mental paralysis.

There can be lots of reasons why we get stuck like this. For me, part of it seems to come from holding conflicting beliefs about style.

On one hand, I believe that what we wear matters. I believe that it can support how we feel, how we move through our day, and even help us understand ourselves.

On the other hand, there are quieter but powerful beliefs underneath that say things like:

"Don’t try too hard. There’s more important things to do with your time.”

"Don’t draw attention. You don’t want to look like you really care about this.”

"Buy your needs and not your wants.”

That tension—between what I say I value and what I may actually believe—creates friction. Psychologists call this cognitive dissonance, and the discomfort it creates keeps us stuck.

Thinking Isn’t the Same as Doing

The more I sit with this, the more I’m realizing something simple (and obvious): merely thinking about style is not the same as engaging with it.

At some point, action has to enter the picture. Action is what speaks back to the mind. It’s one thing to decide that style matters to you. It’s another to actually engage with your clothes—to try things on, to experiment, to notice what works and what doesn’t. Over time, those small actions begin to reinforce the value you say you hold. They make it real.

You can’t merely think your way into what must also be a lived out experience. Aligning your actions with your thinking reduces that "stuckness".

Making a Mess in the Kitchen (of your style)

Kristen Caine has used cooking as an analogy for this idea. It immediately clicked for me since I have logged a lot of hours in the kitchen over the years.

Someone can read cookbooks, watch videos, and come to understand techniques. But they can’t expect to host a beautiful dinner party if they’ve never actually spent time working it out in the kitchen.

You have to burn a few things.

You have to figure out, through experience, what works.

You have to be ok with making a mess. That's how we learn.

I know someone who is a very capable cook, but who carries a fair amount of insecurity into the kitchen. It keeps them from relaxing, experimenting, and really enjoying the process. As a result, they don’t fully access the range of meals they could be making—or develop any measure of confidence in their ability.

I would feel completely stifled if I approached cooking that way. I rely on variety (you should see my spice cabinet!). I love trying new recipes—if something sounds interesting, I’ll give it a go. If it doesn’t turn out, I’ll do my best to figure out how to fix it. It doesn't stop me from getting back in the kitchen and making another mess.

Some of my spice inventory. The challenge is to make my wardrobe more flavorful.

Unfortunately, that’s not how I’ve approached my wardrobe. I’m a lot like my friend who has insecurities when it comes to cooking. I’ve kept myself on a similar uninteresting, bland diet. My closet has mostly basics, and it feels kind of blah. There’s not a lot of flavor in what I create from my wardrobe and it’s not a very satisfying experience.

It’s funny how some areas of our lives can operate so differently.

Old Stories Have Staying Power

Another part of the mix that keeps us stuck is that clothing is not neutral.

Many of us carry memories—comments, moments, and feelings of embarrassment or shame—that have quietly shaped how we show up. Those experiences don’t just disappear. They linger, often outside of our awareness, influencing what feels “safe” and what feels “risky.”

Our brains are designed to keep us safe, not necessarily to keep us satisfied. There will be hesitation and resistance (even paralysis) when that sense of safety is threatened.

It makes sense. Fear has a way of doing that.

Creating a Way Back In

If action is the missing piece, the question becomes: how do we begin?

Not with a complete overhaul—but with something smaller, and more sustainable.

This is where making a bit of a mess in our closets begins.

Building a system—or even a simple, doable method—takes time. So instead of trying to solve everything at once, we start small: enough to not feel threatening.

In the acquiring, maintaining, and creative areas of a wardrobe, what might it look like to take a small step?

I'm wrestling with how to approach this over the long run . Yet I do know that this is where I have to begin. Since I had been putting off a few purchases for months, I set a very small goal: place one order at a time until I make it through my very short list.

Over the past few weeks, I’ve followed through—a pair of Birkenstocks, a sweater I’ve been eyeing since before Christmas, and some much-needed pants that aren’t jeans. This is good, but it has to keep going. Taking action has to be in the forefront.

The new Birks. A purchase that was put off for months.

I’ve been fortunate to have a friend keep me accountable. She checks in with me and asks if I’m making progress. I highly recommend this kind of support as a way to stay in relationship with this part of your life.

Making a Mess (On Purpose)

This is what I keep coming back to:

You can’t expect your style to just happen. You have to participate.

You have to try things that might not work perfectly—place the order, experiment with a new combination, wear something even if it’s a little outside the box from your norm.

In other words, you have to be willing to make a mess.

That’s where learning happens. That's where we show ourselves we'll survive working through something that is challenging.

A Small Shift

Maybe the target should simply be to get involved: to move—even slightly—from thinking to doing, from observing to participating.

I’m hoping this could be the beginning of something more structured taking shape—a more intentional approach to making sense out of style. I'm not sure exactly what that looks like yet, but that is why I show up here on this space.

So for now, this is where it starts:

by choosing action over overthinking, and being willing to make a mess.