How to Stop Playing It Safe With Your Style (In Your 40s and Beyond)
It's 2018. I've just landed in LA, and I'm hotfooting it to the train station to catch the Amtrak down to San Diego.
I'm exhausted, slightly sweaty, and trying to get my bearings. All while carrying this weird mix of excitement and dread.
I've been invited to a big 2-day networking event for female entrepreneurs, which sounds great on paper, right?
But in my head, the running narrative was more like:
“You don't belong there. Everyone's going to be better than you.”
“What are you even doing going to this?”
And when that's the energy you're operating from, you don't exactly make bold choices, especially not in what you wear.
What you do instead is edit yourself by packing the safer options, keeping things toned down, because God forbid you're too different.
The edit job I did on myself
Looking back, that's exactly what I did. I decided "this is who I need to be to fit in and be perceived as professional" and I dressed accordingly.
When I got there and looked around the room, the women were wearing bold hats, cool jewellery, and outfits with main character energy. The energy pouring out of them was "I'm showing up unapologetically as myself", and that's magnetic.
"Wow, they look cool," I thought, as I pulled awkwardly at my very dull top and trousers, which were fine, but had zero personality. And don't even get me started on the random decision to suddenly start wearing hair extensions for the first time in my life!
But the impact it had on me went way beyond feeling frumpy and self-conscious. It totally derailed how I showed up.
I felt small, inferior, and like I really didn't fit in — which is ironic because in my head, my original plan (not to dress too differently) was meant to help me fit in. Talk about a backfire!
In fact, trying to be a chameleon impacted how I showed up so much that it cost me connections, opportunities, and, more upsettingly, the joy I could have experienced if I hadn't been so in my head.
And at the time, that pattern wasn't just happening at that event. It was happening everywhere.
Looking back, that’s exactly what I did. I decided, “this is who I need to be to fit in and be perceived as professional”, and I dressed accordingly.
When I got there and looked around the room, the women were wearing bold hats, cool jewellery, and outfits with main character energy.
The energy pouring out of them was “I’m showing up unapologetically as myself” — and that's magnetic.
“Wow, they look cool,” I thought, as I pulled awkwardly at my very dull top and trousers, which were fine, but had zero personality.
And don’t even get me started on the random decision to suddenly start wearing hair extensions for the first time in my life!
But the impact it had on me went way beyond feeling frumpy and self-conscious. It totally derailed how I showed up.
I felt small, inferior, and like I really didn’t fit in — which is ironic because in my head, my original plan (not to dress too differently) was meant to help me fit in.
Talk about a backfire.
In fact, trying to be a chameleon impacted how I showed up so much that it cost me connections, opportunities, and, more upsettingly, the joy I could have experienced if I hadn’t been so in my head.
And at the time, that pattern wasn’t just happening at that event. It was happening everywhere.
And if you read enough social media quotes, you know, on paper, the solution is simple...
Just be yourself. Don’t be afraid to be you. Cool. Great. Love that.
But if it were that simple, everyone would already be doing it, right?
So if you’re where I was, feeling unsure of yourself, maybe not fully connected to who you are, and second-guessing everything, that leap to “just be yourself” might not be one you can manage all at once.
And that’s okay.
Instead, dear reader, you might need to take stepping stones.
The moment it clicked
After the event, I headed back to LA to meet a friend for a road trip to Palm Springs and Joshua Tree. We were cruising along the insane 8-lane highway in a white Dodge Charger (thanks for the upgrade, Hertz), and I was telling him about the experience.
And he stopped me in my tracks:
"But isn't helping women show up as themselves and go after what they want — isn't that literally what you do?"
"Yes," I said.
So why wasn't I doing it?
I knew why. The same reason my clients struggled with it. FEAR. The fear of being yourself and getting rejected or judged. Or worse still, having what you already worried was true about yourself confirmed.
My role — whether it's been in fitness, dating, or now style — has always been to help people reconnect with who they are and feel good showing up from that place. So how could I expect them to do that if I wasn't doing it myself?
You've gotta walk the walk, not just talk the talk.
And what hit me like a wrecking ball after that conversation was this: I'd been working on myself a lot and thought I'd stopped playing small. Turns out I hadn't. I was still holding parts of myself back without really clocking it, and this event had really highlighted it. How I chose to dress was literally the physical incarnation of smallness.
And you know what, nothing changed overnight. But the awareness had been raised. I could see that I was still showing up smaller than I thought I was and that had to shift. I had to find a way to expand how I was showing up because I didn’t want to carry on losing out on opportunities.
Why "just be yourself" or "wear what you want" isn't as simple as it sounds
After that conversation, I didn't suddenly start wearing wildly different outfits. If anything, I was still playing it safe because I didn't actually know what dressing as myself even meant yet.
My outfits weren't terrible.
They were just a bit safe and muted. Like I hadn't quite decided who I was or how I wanted to show up, so everything sat somewhere in the middle.
For a lot of women, style is either the last place their creativity shows up, or the first place it stopped.
They'll paint, make things, express themselves all over the place, but their outfits stay exactly the same.
Or they used to dress with real personality, and somewhere along the way, that just quietly disappeared.
And underneath that, the fear of standing out and being judged; of being properly seen and not liking what came back was still there.
Which is a weird place to be in, because part of you does want to stand out. But another part of you is like... yeah, but not too much
The real cost of playing it safe
Me in San Diego playing it safe. There’s no zing there!
I see this all the time. We say we want to be ourselves, but then we go out dressed as a slightly more acceptable, toned-down version. And sometimes that gets dressed up as "I'm just being practical."
Practicality matters, genuinely. But sometimes when you scratch the surface, it's also just a way of avoiding being fully seen.
And that dilution of self doesn't stop at your outfits. It bleeds into how you show up in a room. The conversations you have. The opportunities that come your way. The people you attract.
If you're not showing up as yourself, what people are responding to is a watered-down version. And in return, you often get a watered-down version of life.
And here's what can be frustrating about the advice:
Being told, "Just wear what you want, express yourself, be bold.”
As theory, yes, in fact F*ck yeah to that!
But as a starting point, it can fall flat, because if the outfits you actually want to wear feel miles away from what you currently feel comfortable in, or you feel unsure about who you are in style terms right now, that's not helpful.
It just leaves you stuck thinking: "Once I feel more confident, I'll start experimenting."
But no, no. That's not how this works.
Confidence doesn't come first. It comes after you start, and it builds through small steps over time, not one big jump.
So if you're where I was — unsure of yourself, maybe not fully connected to who you are, second-guessing everything — here are three stepping stones to start stopping playing it so safe in how you dress.
Three ways to start showing up more as yourself (without overhauling everything)
Step 1: Add one thing that feels a bit more “you”
Not a full outfit overhaul. Just one change.
Look at what you were already planning to wear and tweak a single element:
Swap your usual black top for a colour you’re drawn to
Change your trainers for a pair of shoes with more personality
Add a piece of jewellery you’d normally say is “too much”
Wear the interesting jacket instead of the safe one
Or mix things up slightly in a way you normally wouldn’t — like wearing trainers with tailored trousers instead of your usual go-to
Keep everything else the same if you need to.
👉 Ask yourself: What’s one thing I could change that would make this feel more like me?
Step 2: Keep the outfit appropriate, but stop watering it down
You don’t need to ignore the context you’re dressing for.
But you also don’t need to strip all personality out to fit it.
Keep the structure of the outfit — just adjust the details:
Same formula, but a stronger colour
Same shape, but a more interesting fabric
Same base, but one standout accessory
👉 Ask yourself: Where am I toning this down out of habit — and what would actually happen if I didn’t?
Step 3: Do it again (this is where confidence actually comes from)
This isn’t a one-off. You don’t do it once and then let yourself retreat back to style safety. You have to intentionally push yourself to do it again.
And again.
And again
Because you don’t suddenly feel confident, you practise being the confident version of you who shows up and wears the bolder choice (for you)before you feel ready.
That’s how confidence builds.
And here's what I've noticed: the more you start dressing in a way that actually feels like you and expresses who you are, the less you care what anyone else thinks. Not because you've suddenly become bulletproof, but because when you feel aligned, the confidence just comes from within.
One last thing
If deep down you’d love to be swanning around in a ball gown and a tiara, but your life isn’t exactly set up for that right now…
Don’t swing so hard into “appropriate” that you lose yourself completely.
There are always ways to bring more of you in.
It doesn’t have to be all or nothing.
Even if your version of fully you is a ball gown and a tiara, you don’t have to start there.
(But if you want to… go for it.)
Till next time.
Sarah xoxoxo
