Why It's Time to Wear the Outfit That Scares You

Something in your closet is waiting for you. It isn't the sensible blazer you wear on autopilot, or the safe dress that earns polite nods. It's the piece that spoke to you deeply. The one that felt electric in the fitting room. The one that whispered, "This is you." Then, once you got it home, it went quiet. Or rather, you did.

In this episode of The Visibility Shift, I'm talking about the courage that shows up in small, ordinary moments, where you choose the clothing item you love and dare to be seen in before you feel fully ready. I'll tell you why the hesitation you feel when you reach for what you really want to wear isn't about fabric or color, but the stories you tell yourself.

This is a challenge, not to overhaul your wardrobe, but to run a small experiment in self-trust. To wear the thing, notice what happens, and discover whether the fear you have been protecting is actually guarding a door that leads somewhere freer.

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3:02 – Why you resist or talk yourself out of wearing that one item you really want to wear

6:17 – How Jessie (the previous podcast guest) described her fear of standing out

9:10 – What the fears and excuses are really about

12:07 – What might be waiting for you on the other side of your fear

13:38 – Challenge: how to wear that item this week

Mentioned In Why It's Time to Wear the Outfit That Scares You

How Jessie Spressart Went From Blending In to Being Herself 

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Full Transcript

Welcome to The Visibility Shift, the podcast where style becomes your most powerful strategy for being seen, standing out, and leading boldly. I'm Ellie Steinbrink, stylist and personal brand coach, and if you've ever thought, "My style just isn't working anymore," take this as your sign. You're ready for your next level. And instead of launching into a panicked shopping spree, what you really need is a strategy. A style strategy that reflects where you're headed, not who you used to be or who you think you need to be to fit in.

Because when your style aligns with your brand and your vision, everything shifts. You lead with more presence, you attract the right opportunities and clients, and you fully step into the woman you're becoming. Because showing up as yourself, that's the most strategic thing you can do. Now let's get visible.

Welcome back to another episode of The Visibility Shift podcast. I’m so glad you’re here, as always. So glad you’re choosing to show up here and be with me today.

Last week’s conversation with Jessie really stuck with me. We talked a lot about risk, discomfort, and doing the thing that feels a little scary, even when it would be easier not to. And I kept thinking, we talk about this concept so much in business, or especially as entrepreneurs or running our own businesses, but we don’t talk enough about how this shows up in our closets.

So today, I want to issue you a challenge. A challenge that will get you out of your comfort zone and into a version of yourself that maybe you’ve been wanting to meet, but maybe you’re a little bit afraid to.

I bet you can think of at least one thing in your closet right now that you secretly want to wear or were once excited about, and then for one reason or another, it just never has been worn. It’s been sitting there collecting dust in your closet. Maybe it was something you bought on vacation when you were feeling a little adventurous and really open and joyful. I know that’s true for me. I have this vacation version of Ellie that comes out. It’s much more playful and a lot less serious.

Maybe it was a sale item that you took a bet on. Or maybe it was just something that spoke to you very deeply, like, this is truly who I am. In that moment, you had the courage to buy it. But then it just sat. You would think about wearing it, but for one reason or another, you chose something else. Every single time, you kept choosing something else.

The courage you once had in that moment, when it felt so aligned, it just somehow has gone flat. But deep inside, you still think about this thing. You still wonder, what would it feel like to actually wear this?

Now, there are a lot of reasons why we resist doing something we once felt inspired about. And then when it comes to the reality of actually doing it, there are a lot of reasons why we talk ourselves out of it. One of them might be that you end up doubting yourself because that new you feels uncomfortable and it feels new. You might think, maybe this isn’t my true self after all.

When you come down from your high or come down from that inspiration, you doubt, like, well, maybe that moment was just fleeting. Maybe I was just a little bit too up in the clouds. I was just in one of those brave moments, but it’s fleeting. Now that I’m back down on the ground with my feet touching the ground, this really feels too scary to choose right now. Perhaps it’s just too far outside of who I am, too much of a stretch. What was I thinking? You know, like, that was a mistake.

I think that that happens to me a lot of times, where it’s like, well, you’re just feeling unsure, right?

I think another reason that often will nag us in that moment when we want to reach for that item, but then we hesitate, is maybe there’s a voice inside of you that says, “I’m really afraid that I can’t pull this off.” Maybe I’m not "that person" who can wear this. Or maybe you’re like, “I’m not the person who wants to draw attention to myself.” And the thought of this outfit or wearing this item potentially drawing attention to yourself really makes you uncomfortable.

You know, what if I look ridiculous? What if I don’t style it in the right way? What if people look at me like I’m off my rocker? What if I can’t match the energy of this item or this outfit? What if I’m actually not cool enough to wear this? Like, will I look stupid or like I’m trying too hard? Maybe I’m trying too hard to look young or modern or trendy. It’s just like all these fears are bubbling up to the surface, right? It feels like, oh, this is overwhelming.

So it’s just easier, instead of dealing with all these fears, it's just like, okay, let’s just put it back on the hanger and let it sit there for another year.

Another reason you might be resisting, and this actually came up in my conversation with Jessie last week—so go back and check that out at some point if you haven’t yet listened—but maybe there’s something inside of you that resists because you don’t want to rock the boat.

Perhaps you know what people are going to be wearing to the event that you’re going to, and you know that what you’re wearing maybe will be a little bit different or maybe a little bit off from what everybody else is expected to wear. Maybe it’ll make you stand out a little bit instead of blend in. Let’s be honest, sometimes being the one who’s standing out is really hard.

If you fear being the center of attention—not necessarily that your item will make it so, but you might feel like you’re the center of attention—I can imagine your mind is already going to, like, “What if I freeze up and just wish I could turn around and leave?” Those feelings feel really scary. In those moments, I think it feels easier just to be like, okay, let’s just keep doing what I’ve always been doing because that’s just easier to deal with.

But Jessie described this in her interview last week so brilliantly. In fact, at the end of our interview, she shared that these fears of stepping into yourself and stepping into something that does feel true to you, but maybe isn’t like what you see around you, those fears will continue to nag at you. Even for Jessie, who we had gone through a year of work together, she found herself doubting herself in this moment.

And if you haven’t listened yet, the quick version is that she went to this really high-end, really luxurious event where she knew everyone was going to be really elevated and dressing really beautifully and elegantly. She had chosen to wear these really awesome bright red pants that we had picked out, and then this really feminine polka dot blouse.

She said when she walked into the event, one of the first women she saw—she was like, “She was the same stature as me. We’re both petite, similar”—this woman was wearing these beautiful white pants and a beigey sort of blouse. If you have this picture of a quiet luxury look, that’s essentially what it was.

Her immediate reaction was like, “Oh no, I’m not dressed up enough. I should be looking more sleek, and I need to be looking more refined and elegant. Look at this woman. Maybe I should have chosen something like that.”

But she said, in that moment, I realized I was getting caught up in my own lies. I was getting caught up in a story. And the story was that dressing like this woman was how we should be showing up, when in reality, that is not in alignment with who she is and who her true and authentic self is.

So she says in the interview, “I had to just check myself and say, that’s actually not what I want. What I want is right here. And I know what I’m wearing is aligned, and this is going to actually help me bring out my most authentic self.”

I’m curious, what other reasons do you say to yourself about why you can’t wear this item? And let’s just get off the table that it doesn’t fit. I want you to be imagining an item that you can go into your closet and wear right now. I don’t want fit or sizing to be an issue because I think that just muddies up a lot of things. If it’s not even a possibility—like you had it 10 years ago and now you’re not the same weight and you can’t wear it—okay, let’s just take that off the table for now.

There has to be something you’re thinking about in your closet that you could go put on right now. What other reasons are you telling yourself why you can’t wear this?

But today, just today, I’m going to ask you to let these excuses, to let these fears, go to the wayside. I want you to look yourself in the mirror and say, “I owe this to myself to give myself the chance to see how I feel when I put this on, to see how it feels when I take it out for a spin, to let people look and see me, and to be okay with that.”

I mean, after all, you’ve never actually tried this. You’ve never actually taken that item out for a spin to see what actually happens as a result. All of these fears and excuses that come up for us about why we can’t wear it, those are just things that we think will happen. They’re stories about what we think might happen. We’re projecting. But that isn’t what is actually going to happen, because we don’t know. We haven’t done it.

I truly believe these excuses, and trust me, I’ve been there. I’ve had episodes of this podcast where I’ve talked about finding myself going down a different path of needing to wear this, that, or the other thing, and realizing that’s not actually the authentic version of me. So I know the excuses we make for why we can’t wear something or why we can, it’s a protection mechanism.

We use these excuses and these reasons to protect ourselves from whatever we fear. Maybe it’s looking stupid, where that could lead to a statement like, “I’m going to lose my credibility.” Or maybe the fear is standing out, which means I won’t fit in. Or that I’m being too much and I’m going to draw too much attention to myself. The fear may be, “I’m trying too hard. I might be seen as a fake.” Maybe your fear is offending someone.

So if your goal is to make people comfortable and happy, then that fear would come to life if the perception is, “Oh, maybe someone will be uncomfortable with what I’m wearing.” Or maybe your fear is criticism. Your self-worth and your self-esteem thrives on praise and adoration and getting that little check mark to make sure everything’s okay. Or maybe your fear is failure. “What am I worth if I fail, if I can’t pull this off?”

This may all seem way too deep for just talking about wearing an item of clothing that you’ve never worn before. But in my experience over the last five years of working with women and hearing them talk about why they can or can’t wear certain things, these are the true reasons why we hold ourselves back, why we don’t allow ourselves to try something, to take a risk, to go on a different path.

This fear, whether we’re aware of them or not, they are so great. It doesn’t seem, at the moment, if we don’t question that thinking, it doesn’t seem worth it to see what might happen on the other side of that fear.

But just today, consider what if. What if you find on the other side of this fear, on the other side of wearing this item, what if what waits for you on the other side is so much greater that it’s worth it to work to let yourself walk through those fears? What if you wear this item and you experience true liberation?

That was actually something Jessie said on her interview last week as well. She felt liberated when she dressed in a way that felt totally aligned. What if you wear this item and you feel a renewed sense of energy and aliveness, like you didn’t even know was available to you anymore? What if it actually draws people towards you? They’re curious. They’re like, “Who is this?” instead of pushing them away.

So I’m curious, what is this one item you’re thinking about right now? I can bet it wasn’t hard to call to mind this item because you’ve been thinking about it too, haven’t you? You’ve been wondering if you have the courage to wear it. You’ve been wondering, “How would this feel?” And you probably have been tired of having this internal battle of whether or not you should wear it and wish you could just get over yourself and do it. You’ve been wondering what it would feel like to get a snippet of a different version of you, perhaps a truer version of you.

So here’s the challenge, and I think you already know what it is. I want to challenge you to wear that item this week. I want you to find a day when you can make it happen, and I want you to do it. If you’re up for this challenge, I want you to commit to it. I want you to schedule it on your calendar, if you must, whatever you need to do to ensure that you will keep your promise to yourself.

Now, the second part of this challenge is to ideally wear it in a setting where you will be seen. Let people in on this version of you that feels most true, that feels exciting, that feels alive. Trust that your gut instincts are not wrong. But honestly, truly, if wearing this item in public truly terrifies you and you just cannot bring yourself to do it, at least please promise me that you’ll wear it around the house. You’ll take it for a spin. Maybe you’ll wear it while you’re working and you don’t have any calls that day.

While you wear it, you may need to give yourself a pep talk like Jessie did, like Jessie described in her interview last week. You may have to remind yourself, “I'm okay. Nothing bad is going to happen. I’m safe. I’m doing this for me. I’m doing it because it makes me feel like me, makes me feel alive, makes me smile, brings me joy.” Let that be your driving force.

Then I want you to note how it feels when you allow the fears to subside, when you allow the fears just to take a backseat and say, “Hey, you’re not driving this bus today.” How does it feel to really let yourself experience the emotions that come up? Does your disposition change? Do your behaviors change? Do your actions and outcomes change on this day? What happens? What did you notice?

And I’d encourage you, after this is all done, or at least in the 24 hours following whenever you wore the item, to journal about the experience. And yes, I know this sounds incredibly silly and ridiculous, but based on what we’ve discussed here today, I think you may be realizing that what you’re allowing yourself to do is quite revolutionary.

I’d love for you to get your journal out, sit, capture those feelings, and let them come alive in you. Let them propel you forward. Let those feelings give you the courage to do more of this. See what opened up for you. What did you discover? Is there something in there that you’ve been holding back or hiding for a really long time in this experience? Like, really let you see it?

This is really how the change starts, you guys, in these small, brave steps. And I know you can do this. So if you’re listening and you decide to take me up on this challenge, I would love to hear from you. Please message me through whatever podcast platform you’re listening on or go find me on Instagram, on LinkedIn. I’d love to know, what did you wear? What did it look like? Send me a selfie. How did it feel? I’d love to cheer you on and also celebrate this feat together.

But I want to say it again. Do this for you. Do it for the version of you who is ready to come out and be alive and feel joyful and show her true self. There is freedom there. I’d love for you to experience just a little taste of it, because when you get a little taste of it, you will want more of it. Who knows where it might lead you?

Who’s up for the challenge? I would love to know. I would love to know. I’m going to leave you with this, and I can’t wait to see you back on another episode.

Thanks for joining me on The Visibility Shift. If something in today's episode made you pause, rethink, or gave you permission to stop playing small, it would mean so much to me if you'd leave a review at ratethispodcast.com/visibilityshift.

If you're ready to stop second-guessing and start showing up as the leader you are from the inside out, The Visibility Edit is where that shift begins. Head to elliesteinbrink.com to learn more and join the next round. Because the next version of you, she's not waiting for permission. She's waiting for you. Let's make it visible.