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3 lessons in using style to express yourself at work

Updated: Jun 29, 2022

Part 1 of 3 in this Style Series.

Style isn't "frivolous". It also doesn't have to absorb all your time & attention.

Here are 3 most impactful lessons about style I've learned over the last 5 years.

  1. Wear what the f*ck you feel good in... and you might just get better at your job.

  2. It's okay to show people behind the mask [and we can use style//clothes//makeup as a mask]

  3. You can find your style sweet spot. It's worth looking for.

I have traced them back to the original catalysing idea & teacher... and how it has impacted my life.

Each has been accompanied by inner confidence work. I will share in #3 of this Style Series.

To go deeper in this work & define your own style, outer appearance, and the inner confidence: explore Style Revival.

An important note:

These lessons are all from my lived experience as an able, white woman growing up in a position of privilege. I know that not everyone has the benefits that I do, especially when it comes to perceptions of professionalism, beauty/style standards, and grooming. For example, people of colour have been systematically repressed from wearing their hair in natural styles [learn more about hair discrimination in this beautiful post by Trisha Opolot].

I acknowledge this with frustration and a desire to be part of the solution.

Our narratives around style, beauty, and professionalism are starting to change. Slowly. And these changes disproportionately benefit knowledge workers, specific industries & people who often have already experienced compound privilege. Myself in this category.

So I share from my own experience, but I would love to hear yours too. And if there are ways I can improve how I understand & speak about style to be inclusive of everyones' experience, please share feedback with me directly [here is my email].


Lesson #1 Wear what the f*ck you feel good in... and you might just get better at your job.

Along with:

  • Outfit repeating isn't a sin [even when it feels like people will care].

  • You don't have to "dress for the occasion" or for others. You can dress for yourself.

  • A style decision once can GIVE you so much time back daily.

  • It's okay to stand out. It's okay to dress differently to your peers.

Catalyst: Tools of Titans, by Tim Ferriss [book] This small paragraph changed my life. [so did many other small paragraphs. One of the most profoundly impactful books in my life so far]

"Steve Jobs had his black turtleneck. Chris Sacca has his embroidered cowboy shirt. He bought his first one, impulsively, at the Reno airport en route to a speech, and the reaction prompted him to buy out half the store on his return. A shirt might seem like a small thing, but Chris realized early on that being a successful investor isn't simply knowing which companies to invest in. Part of the process is ensuring founders know who you are. If a single shirt can create seemingly unending media mentions and doesn't hurt your reputation, it's low-hanging fruit. On top of that: "It also saved me a lot of time thinking about what to wear and a lot of money that would have been wasted on suits."

How it changed me: It was white pants. When in white pants I felt creative, expressive, and bold ;) I made it so easy for myself. A wardrobe section of white pants. Then another with tops that suited. Those 10 mins extra each day that I would have spent deciding on outfits, I invested back into my own enjoyment of life.

If you saw me anytime in 2018/2019... it would have been in white pants ;) Reflection questions for you:

  • What do I love wearing?

  • If I wasn't worried about what others would think... what would I wear for work?

  • Where do I currently feel confusion, annoyance, overwhelm when it comes to my style?

  • What would it feel like for my style to be effortless & easy each day? What would I do with extra time/energy/money?

Dive deeper into these questions & resign your own style with us in Style Revival.

Lesson #2 It's okay to show people behind the mask [and we can use style//clothes//makeup as a mask]

Along with:

  • Vulnerability is powerful. It creates connection.

  • Being vulnerable with others also allows you to accept yourself & quieten down the self-critical voice.

  • There is immense power in "going first" and doing what others aren't.

  • It is safe to love the me I see in the mirror.

  • The me behind the mask is just as worthy of love, acceptance, and belonging.


Without a doubt, Brené Brown. Her 2 TED talks.

The power of vulnerability

"These are whole-hearted people, living from this deep sense of worthiness... these folks had, very simply, the courage to be imperfect. They had the compassion to be kind to themselves first and then to others, because, as it turns out, we can't practice compassion with other people if we can't treat ourselves kindly... The other thing that they had in common was this: They fully embraced vulnerability. They believed that what made them vulnerable made them beautiful... They talked about the willingness to say, "I love you" first ... the willingness to do something where there are no guarantees ..."

Listening to shame

"Life is about daring greatly, about being in the arena. When you walk up to that arena and you put your hand on the door, and you think, "I'm going in and I'm going to try this," shame is the gremlin who says, "Uh, uh. You're not good enough. You never finished that MBA... I know you don't think that you're pretty, smart, talented or powerful enough..." Shame is that thing. And if we can quiet it down and walk in and say, "I'm going to do this," we look up and the critic that we see pointing and laughing, 99 percent of the time is who? Us. Shame drives two big tapes -- "never good enough" -- and, if you can talk it out of that one, "who do you think you are?"

How it changed me:

For 4 years, I stopped wearing makeup daily.

There is nothing wrong with makeup [and I have some new thoughts on it! See next section].

But I used this to heal my self-talk.

The voice that said I wasn't good enough unless I had makeup on. That would do a little "ughh" recoil in the mirror each morning before "putting my face on".

I judged my skin that is prone to spots & redness. I didn't like looking too "young".

At work I had stories that I wouldn't be taken seriously / respected because of my age, appearance etc.

But I decided that seeing my beauty & worth detached from my "mask" was worth it. To let people think what they would think.

And by letting others see the less-perfect me, I could start accepting it, too.

Reflection questions for you:

  • What about your appearance do you feel shame, guilt, a desire to hide, mask, or deflect?

  • How would it feel to be free from this?

  • What about yourself do you feel you need to hide at work?

Follow us on Linkedin for Style Series #2. This will dive into the inner confidence work that supports your authentic expression at work.

Lesson #3 You can find your style sweet spot. It's worth looking for.

Along with:

  • Feeling stylish & expressive doesn't have to take a lot of time.

  • It's not simply vanity/societal conditioning to care about your style. You can do it for you & that is a good enough reason.

  • You can own your beauty. Every part of you.

Catalyst: Mama Gena, in Pussy: A Reclamation [book]

"I wear clothes I love every day, even when I'm just staying home. I have figured out a simple way of handling my hair so it always looks pretty great. I have a brief makeup routine - a dot of concealer, lash curler, mascara, and lip gloss. It's easy to put on and makes me feel like I have some extra sparkle."

How it changed me:

Emerging from my no-makeup healing period... I'm now finding my own expression. And it does involve some experimentation & play with makeup, outfits, style.

But I'm also determined not to let it consume me [even though I love Pinterest, Youtube tutorials, and the general fabulousness of people on the internet].

I love nurturing myself, adorning myself, and allowing space in my day for playing with style. But I'm doing it on my terms.

And wearing what I love has included bright colours, silky fabrics, a fabulous [faux] fur coat... and even doing creative writing in my fave lingerie and heels.

Reflection questions for you:

  • How would I dress / style for work if I was doing it purely for myself & my own expression / amusement / enjoyment?

  • What would it feel like to fully own my beauty?

  • What makes me feel fabulous?

Ready to play? Join Style Revival.


Those have been 3 of my lessons so far about style & expression at work.

I am excited to learn many more as I go. Something I have decided is that my style will evolve with me. It can change at any time. Things that were important & core to me before can be let go whenever I like.

We are diving much deeper into outer appearance & playing with your style as part of Style Revival. This is a brand new program from Work Well Warriors.

Unlock your own expression.

Curate an inner & outer reality that you’re quietly (or not so quietly) in love with.

Join us now for Style Revival.

I'm Stephanie Brien - call me Steph. I lead the Work Well Warriors team.

[connect on Linkedin or Instagram] I help growth-focused humans get unstuck and find new possibilities. To explore work & life on your terms... then ground that in practical tools you can use day-to-day.

I did all the things I was "supposed" to. Studying business, psychology, and writing a thesis on motivational theories. The job I landed in was great... until it wasn't. Burning out, experiencing complete mental exhaustion until I had nothing left to give. I wish this story wasn't so common. But it meant that I started to experiment. To step outside of the normal "rules" of work & life and started to explore. On my terms. I'm here to help you find your own direction for work & life on your terms. Whatever that looks like for you. To guide you with a blend of playfulness and ease, backed with structure and tools. I can't wait to connect ✨

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