The Self-Esteem Struggle: Wearing Your Worth

Growth, it’s all part of the human experience, and it can be both very fulfilling and very uncomfortable. Some people actively seek growth, and some avoid it at all costs. The good news and the bad news is, it’s coming whether you like it or not.

A common growing pain that I see within my clients is understanding their worth- as business women, as friends, and as a wife/girlfriend/partner. This automatically translates over to their wardrobes. For example, these women are still dressing like an entry level employee when they are in fact, running the company.

Not dressing the part, seems innocent enough, right?


The snowball effect of this is catastrophic. How do I know this? I’ve not only witnessed it with the women I’ve worked with; but I’ve also experienced it myself.

My career was not some overnight success or some lighting bolt of good luck (as some may see it from the outside), it was a journey of sweat, blood, and tears. From living off of unemployment while interning at 28 years old (also being the oldest intern on set), to working as an admin to the company I now own half of (School of Style) and starting my own styling business from nothing AND on top of my already large workload.

As Drake would say, “Started from the bottom now we here.”

drake milhouse

But where is here? In the dark side of my mind, “here” is a girl who is terrified she’ll be “found out.” Found out as someone who doesn’t deserve this level of success. Like, getting where I am today was some mistake that will eventually be sorted out, and I’ll be back at the bottom where I belong.

Can we say self-esteem issues?

The reality is, I work my ass off. I work nonstop; I’m smart as a whip, and I deserve every bit of success that I’ve earned – yes earned.

However when those dark thoughts wander in, it reflects in my wardrobe (yes, me the stylist). I have experienced the burn of people thinking I am my business partners assistant. I cringe every time someone thinks I’m 22 years old (I’m 35). There were days where I’d look in the mirror and say, “Is this what a successful entrepreneur looks like?” It’s not that I looked bad, but what I was showing the world was not an accurate representation of myself.

Should I care what people “think” of me? Probably not. However, my perceived reaction from other people’s thoughts affects the way I operate in life. Operating out of a place of low self-esteem and low self-worth is never a good thing.

This may come as a shock to you, but nine times out of ten, the way we dress is a direct reflection on how we feel about ourselves. We think it’s because we like it, or it’s because we don’t have time or money – but the reality is we are dressing to level we think we are worth.

lauren messiah

So I challenge you (I’m going to do it too) to write down all of your accomplishments (no shortcomings allowed)- in business, in life, in love and start dressing to a level that matches your accomplishments. You don’t have to be rich or a CEO of a company to do this, maybe you volunteer and has helped thousands live a better life … that count big time of the worth meter, so does being a really good friend or wife.

Easy example:

Have a big meeting? Put down the outfit you wore two promotions ago, and put on an outfit that says ‘boss.’ Try it. C’mon. At the end of the day, write down how YOU felt and how you were perceived by others. Did you feel more respected? Did your look match your personal worth? I am willing to bet that you did.

I want to feel even better about myself, so I’m going to remember to practice what I preach. Low self-esteem is never chic. Try it out and let me know how it goes.

6 thoughts on “The Self-Esteem Struggle: Wearing Your Worth”

  1. I totalky agree. I am 31 getting 32 in september and i think i am dressing too young. A woman thought recently i was 18. This blog inspire me. I need to change some things from my wardrobe like a flowered skater skirt i have. Thanks

  2. Lauren thank you for being so transparent. Your message spoke to my heart. Though I read a few days ago I felt a strong need to share how you have inspired me. I’ve learned to embrace my ‘youthful’ face ( seemingly 10 years younger according to others), but also a bit tricky in business environments, esp. as a creative b/c it translates to young, unprofessional and “too different” to others. This is a great topic and one that others also ask me how to overcome. Cheers to you!

  3. Your absolutely right About everything I have completely neglected myself due to routines and sometimes bywhat others might think, I worked for Yigal Azrouel before and do know a quite a bit about fashion none the less sometimes I do feel being judge because of what I wear compared to what others are wearing knowing I’m perfectly capable of accomplishing the same if not better. I will say sometimes getting caught up in surroundings or change of enviroment can also stray you away from what you actually love . I’m definetky getting rid of my cookies from the closet. 40 year old mom of 3

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