The Compliment Trap and How to Reclaim Your Personal Style

Style is about more than just your appearance. It’s a leadership tool that reflects personal authenticity and vision which requires breaking free from external validation patterns. When you do so, you build self-trust, express your true identity, and ultimately enhance your presence and success.

In this episode of The Visibility Shift Podcast, you’ll hear about the importance of developing a personal style that authentically reflects you. I’ll highlight common struggles women face with their style choices and what drives them, how external influences affect those choices, and how to begin your journey to align your style with what’s on the inside.

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2:35 – How I almost pressured myself into a buying decision that felt wrong despite it “checking all the boxes”

6:21 – Examples of stories I hear from clients on the slippery slope of seeking style compliments

10:04 – How social and professional rules and norms can impact your styling choices

15:58 – The importance of self-trust and being aware of any need for approval

17:55 – The re-evaluation process I recently underwent when I felt tempted to waver from my personal style

21:25 – An exclusive container for ambitious women ready to step up to their next level

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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.

I love a good compliment on my outfit, don't you? I don't think there's a woman here listening that would disagree with that statement. I mean, doesn’t it feel great when someone notices you and says something awesome about your outfit? It makes your day, right?

Even when I ask my clients after we've been doing some work together and we've gone through the shopping and styling and I'm asking them, "How's it going?" they say, "I felt so great today. So many people complimented my outfit." And I say, "That's great. I love that for you." But there's a slippery slope that can happen sometimes when our style is driven by compliments.

And it's why sometimes when women will come to me and they want to work together and they say, "You know, people have always described me as stylish or looking really put together or just looking great, but why is it that I don't feel great on the inside? Why do I still not feel like I'm stylish or I still don't feel like I'm hitting the nail on the head here?" Why is that?

This is exactly what I want to talk about today in this episode, that sometimes in the process of looking for compliments, being comforted by compliments, changing what we wear by compliments, that can actually lead us to losing our voice in the process of finding a style that's authentic to us.

I want to talk about how we can just start to become more aware of this and what we can do to start reclaiming a style that actually does feel like us.

I want to tell you a story, and I think you guys can probably all relate to this. I was shopping last week—I was at Anthropologie—as I was walking around shopping, I saw this dress that I had been eyeing online. And it was on the rack, the rack where they have the online returns.

It just happened to be on the rack of returns. There it was looking at me in my exact size, and I was so thrilled. I was so thrilled. I grabbed it up immediately. I took it with me into the dressing room. I tried it on—actually, this is what I did—I waited to try it on last.

Do you guys ever do that? Where you try your favorite thing on last, because you're just putting so much hope into the fact that this thing is going to be the thing for you? Yeah, that was me. I try this dress on and I had said something to the woman who was working in the dressing room. I told her the story. I was so excited about how I've been looking for this and here it was, it was online only and now here it is in store. It must be fake.

I was already building this dress up to be such a big deal in my mind and I was putting a lot of weight into this working out. So she said, "Well, you gotta show it to me when you put it on." Like I said, I waited to the very end to try it on—all the other things that I had in the dressing room with me—and I tried it on at the very end.

Put it on. It fits my body beautifully. It checks all the boxes, okay? In terms of fit and working for my particular body type, I loved the colors. But I couldn't put a word to it, but my gut immediately was telling me, "This just isn't right."

You know where externally all of the pieces are working together, everything seems on paper like it should work, but just something inside doesn't feel like it's working? That's the feeling I had. And I was like, "No, no, no, no." That's what my mind was saying. "No, I really want this to work out. Why am I not feeling it?" Because it's checking all the boxes and it's here so it must be fate. And I was going down this rabbit hole.

As I'm trying to wrestle with my decision, I'm hemming and hawing and not wanting to take it off, I remember that I had promised I would go out and show the woman who was working the waiting room. I was going to show her the dress.

So I walked out, and as it turned out, she was nowhere to be found. But there was another woman sitting there waiting for someone to try some things on. As soon as I came out, she said, "Oh my gosh, that dress. That dress is perfect for you."

I just said politely, "Thank you," and then I returned to the dressing room. And here I was, feeling so conflicted because I knew I had this gut reaction that said, "This is not the dress. I want it to be the dress and it's checking all the boxes."

Now I've got some feedback from a woman in the waiting room who's telling me this dress looks great on me. Then I start texting my sister and I'm saying, "Oh my gosh, look at this dress I found." And seeking for her to give me another compliment.

Without even realizing what I was doing—I realize it now—but I was wanting her to give me another reason to buy this dress when inside I knew it just wasn't right.

Tell me you haven't done this before. You guys are going to be glad to know that I stuck to my guns and I trusted my gut and I walked out of that store without the dress. And I'm not going to lie and say that I didn't go back, look at it online, and check it another thousand times before really coming back to the decision that this dress wasn't for me.

Now I've heard this kind of story from my clients too. In fact, I'm working with a woman who is a really amazing speaker. She's fully booked out for the year and she's been getting herself on bigger and bigger stages.

One of the things she told me when we started working together was, "I get a lot of compliments on my outfits. You know, there are certain elements of my outfits that I consistently get feedback on." That makes me want to wear those again and again and again.

But here she was meeting with me because she felt like her style really wasn't matching the big energy that she knew she would bring to the stage, the energy that is in her content, the energy that is in her presence. She said, "These clothes, even though I'm getting complimented on them, they are just not meeting the level that I know I'm meant for."

I hear lots of stories like that. I also hear stories of women getting dressed for big events, whether that's a speaking event, a networking event, or maybe a conference they're going to where their outfit is really important.

And tell me you haven't seen these. But what do we do? We go and we buy four outfits, and then we put them on Instagram and we ask everyone to vote on their favorite outfit.

And I'm going to tell you guys, I’ve done this before too.

I have, and it's within the last five years. I'm a little bit sorry to admit, but I'm human too. Everyone has this desire to want to know that they're safe and that they fit in and that people are going to like them, right?

Even me—until I've actually done this work and really honed in on what I want for myself and that I'm okay with the fact that what I want for myself isn't always going to be the most popular choice, I'm okay with that now, but that is something that takes time.

I even see this in a lot of women when we're talking about their colors, what their favorite colors might be, actually, in my work, what we do is we define a power color, I will see this often when I'll say, “What do you think is your power color? What is the color that you really love wearing?” And they'll say, “Well, I get a lot of compliments when I wear blue because it lights up my eyes.” So then, because they're getting complimented a lot on a certain color, that now becomes their power color.

What I'm asking you guys here to consider is that maybe the way in which we've developed our style hasn't been done in a way that has been led internally. Perhaps it's been done in a way that has been led externally.

And the reason I'm bringing this up is not to make you feel bad. Trust me, I'm not here to make you feel bad because I just shared how I can fall into this trap so easily. But I'm here to bring this message because I want you to know that there's a bigger thing going on here, and that over time, when our goal (without even realizing it) is to get external validation, to get people to say, “Yes, I love that on you,” over time, that chips away at our self-trust.

That chips away at us being able to put a stake in the ground and say, “This is what I like. This is what makes me feel good.” That's the thing, isn't it?

I know that there are times when I have gotten compliments about what I wore, but it just didn't feel right to me. Just think about the number of rules we've been given in terms of how to think about “dress for success,” for example. That whole topic, that whole set of research around what it means to dress for success.

We can be checking off all the boxes, about wearing a blazer. What does that mean externally? How does that communicate something to the people around us?

So there's tons of examples in our work lives where we know if we dress a certain way, it will elicit a certain response or it'll make us feel like we're fitting in. But it doesn't necessarily give us that good feeling on the inside.

In fact, I had one of my clients, where we were working, she had just left a very long career in corporate and was now working in her own business. And she said, “You know what? I find myself wearing, there's always an element of black in my outfit.” She's like, “I don't know why I do this.” But what we defined eventually as her style was a very bright, colorful, bold, playful, feminine style.

And she said, “But I still always feel like I need to ground my outfit with black. Like I'll wear this really fun top, but then I need to wear a black pair of pants.” She's like, “It kind of drives me mad.”

But behind it all, what we discovered is that there was a meaning in wearing black for her. And that meaning was, “I will be taken seriously. I will be seen as credible.” Because, you guys, if you've ever been in a corporate environment, you know that that is the code. That is what we've been taught, wear the suit, wear the black, wear the neutrals, wear the bland colors. That's what's going to make you look credible.

But the problem is, in the example of my client I was just describing, she was doing the thing. She was showing up wearing the black in some form in her outfit, but she wasn't feeling herself. So there was a disconnect there.

I'm telling these stories because I want you to recognize that, first of all, we're all in this together. You're not doing anything wrong. But I do think that there is a time where awareness really can be the thing that can propel you in a new direction.

So I just want to reiterate, you're not doing anything wrong. But I want you to recognize that the louder the compliments are, and the more you're getting, and the more you're craving that and chasing after that, it might be a sign that you're performing.

You may not even realize it. You may not even realize it until just now, this moment as we're talking together.

I had another client—a different client—tell me that she was going out on a date night with her husband, and she had found something in her closet she hadn't ever worn. She had bought it and was really excited about wearing this. It felt very bold. It felt very different for her. It felt exciting.

And she had the courage to go put it on, and she came downstairs. And this is no discredit to her husband, but he was kind of like, “What? What's this?” Because it was different than her norm. He wasn't ready for it. He was like, “Oh, what's this?”

And again, no discredit to this husband and how he responded, but this happens so much. In fact, I can't tell you the number of times that I will come out in something out of my own closet that I feel really great in, and either my husband or my daughter or my son has some comment to make. And it's not necessarily the most encouraging comment.

But you know what? It's in those moments that I'll say my favorite response: “Well, I'm dressing for me. I'm dressing for what makes me feel good, so you get no decision in this matter. I'm sorry.”

But it does take a lot of courage to get to that point, right? I get why we get stuck in these patterns, I really do. Because there really are rules and expectations everywhere around us. We've been taught these rules and expectations since we were little girls. We've been taught how to dress to be feminine. We've been taught how a woman dresses in the workplace.

We went through COVID, we went through a time of COVID, and now everyone in the office is showing up in a really casual way. Well, maybe that isn't your way. I mean, I know that's the case for me. The thought of showing up in athleisure in a work environment or even in my own office here doesn't feel right to me. But that is the code now that has been set.

If you're sitting thinking, "Oh, no, should I not be doing that?" That's not the point. If that's what feels great to you, and it makes you feel your most alive, makes you feel most yourself, then hey, I'm all for it.

What I'm saying is, for me, that doesn't fit for me. But you can see how there is a real pressure to want to conform, to want to show up and do what everyone's doing, to dress the way everyone's dressing. It's a real temptation.

We all have this human desire to want to fit in, don't we? I know I do. When I think about where this first starts, it starts early.

I have a 13-year-old daughter, and when I drive her up to her school, I understand why she's wearing what she's wearing. Because I see the clothing choices she's making. I see almost everybody else wearing those at her middle school.

It's because we want to fit in. And what does “fit in” mean? It means safety. Sometimes we might make it mean equal success.

What I want you to consider here and just reflect on is that amidst all these rules we've been given, oh my gosh, it's so exhausting. Amidst all these rules that we're trying so hard to follow so that we can get approval, so that we can get success, so that we can get safety, so we can get comfort, I think we're getting lost in what maybe we love and what we want for ourselves.

So is the way you're dressing something that you really love, that actually lights you up, that makes you feel something inside? Or are you dressing in a way that you know will get you approval or praise?

I don't want you to feel discouraged. This is just a wake-up call. The women I'm working with are women who are doing big things. They're going big places. They're making big moves.

Honestly, dressing in a way that expresses your truest self in an authentic way, where you're gaining your approval only, that is a sign that you are a leader. That is a sign you're not here to play small. "I'm here to step out and lead."

We know this because we've been doing this on the inside or in the way we lead, but now it's time to reflect that on the outside. So this whole conversation—dressing for approval or dressing to maybe keep up with the trends—I get asked a lot of questions about, “Is what I'm wearing current?”

Maybe if you're one that doesn't relate to following trends—I know a lot of my clients don't feel compelled to do that—but we still want to know, are we relevant?

So it becomes less about a conversation of, “Am I relevant? Is what I'm wearing on trend?” It becomes more about an exercise of trusting yourself and having the courage to trust yourself. That’s what this is about.

And I want to share a really quick story just so you guys know that this is a process—learning how to dress and develop your style from a place of self-leadership and self-trust—this is a process that takes consistent effort and consistent work.

So I have a trip that I'm going on where I'm going to be going to a very exclusive event, and I'm going to be surrounded by many women who I am looking up to. I am looking to be in their level. I want to be there. I want to feel like I'm a part of this group.

I gotta tell you, I'm stressing out more than I should about what to wear because I know the women I'm going to be around are at a next level. I know that there's going to be a photographer and a videographer there, and I want to nail it.

There is a great temptation to want to know how everyone else is dressing at this event. I find myself, as I walk into my closet trying to pick out the outfit, thinking, “Well, what will everybody else be wearing, and how can I show up in a way that will be aligned with that?”

Instead of going back to what I know I can lean on, which is: “What is going to make me feel great? What is going to make me feel most like myself?”

And when I honestly answer that question, first of all, I know that outfit is in my closet. I don't need to go panic shop, which is a whole other episode. I know that the way that makes me feel my best is when I'm being creative, when I'm being bold, when there's some femininity to my outfit, when there's a classic touch.

These are all my personal style words, which is actually something I work with on my clients and in The Visibility Edit that's coming up this September. We will work on your personal style words.

I'm having to go back and just re-anchor myself in what is a reflection of my personal style that I know will always make me feel my best and will help me show up in my best energetic self that day at that event.

As opposed to wearing what I think will help me fit in, wearing what I think will be the code for the evening, and then probably feeling awkward and not like myself at all, and then my energy is off. Do you see the difference?

So while I know what I'm asking you is a courageous move—I know this because I've been there—I am in it. I know it's a courageous move to show up and wonder, “Will I fit in?”

But that's the trick. That's the trick. That's the lie. We've all been told that if we show up and be like everybody else, it's going to solve all of our problems.

If you've ever gone and actually truly worn the outfit that you wanted to wear to an event and you felt the energetic shift, you know that that is the pathway to your goals.

Let's just take an honest look at our closet, shall we? Let's just take a look at those moments when we feel frustrated by our closet because we don't feel the way we want to feel in our clothes.

Let's stop blaming and making ourselves feel bad about those choices, and let's start to move towards a direction where you can actually reclaim your authority, where you can reclaim some self-trust.

And it takes time and it takes awareness, which is what we're doing today. It also takes giving yourself permission to slowly make that change, and to know that you're not going to please everybody in the process, but you're pleasing yourself, and that's honestly the most important thing.

If you guys are ready for this kind of a shift, I would love to invite you to a program I have created. An exclusive container of ambitious women just like you who are wanting to make things happen, who are going to their next big level, who are feeling that shift.

I've created a container called The Visibility Edit, which is going to be launching this September. I would love for you to come and apply to be a part of this experience. Because this is the very thing that we're going to be talking about.

This isn't just about going and shopping for a new outfit, it's about rooting deep into yourself and getting honest about what makes you feel alive? What style is going to bring you to life and show the world who you are?

And guess what, guys? That's where the magnetism really happens. It isn't about following trends or following what everybody else looks like who's out there on the speaking circuit.

It's not about that. It's about digging deep and finding what makes you tick. That is what makes you unstoppable. That's what brings the dream clients. That's what brings the dream partnerships.

That's what invites you to the bare stages when you can really get clear on who you are and where you want to go and it all starts here. So I would love to invite you to apply to join the Visibility Edit. I would so love for you to be there and take this journey with me. With that, you guys remember to give yourself some grace, to give yourself permission to start going towards what you love, and just give yourself some credit for being more aware now. Because that is truly the first step to a transformation. We'll see you in the next 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.