Curating Your Personal Style as Your Business Grows

One of the most exciting things for me as an entrepreneuress is the fact that I can play with my personal style. I remember back in my corporate days, I was nervous to push the envelope too much with certain outfits. I was even nervous to show my (very tasteful) forearm tattoo around certain executives. As an extremely creative person, this was really hard. It was yet another sign that I was living a life that did not feel true to me. It was yet another sign that I was not free.

My style has certainly evolved since leaving my day job at MTV in 2014. When I first began running my business full time, I still felt I had to wear certain things to appear “professional” when I did things like news appearances or attended business meetings. I almost always stuck to boring blazers and basic pumps, and never really experimented with fun colors or hair styles. Fun fact: I was scared to even put my hair in a ponytail during my morning news appearances because I didn’t want to look too young! (Do you see how inauthentic living can be super dangerous?) I blame it on the fact that I was basically brainwashed by the “business casual” world, and if you’ve ever had a 9-5, I suppose you have been, too.

But over the past year and a half, I’ve taken lots of leaps with my style and I can finally say I feel totally comfortable in my own skin. I wear what I want, and I use my style as a form of self-expression for myself and my business. I also know that my style isn’t going to appeal to everyone. Some people may think it’s the coolest thing in the world to read books by a pink-haired life coach, others may cringe at the thought. Ultimately, that’s on them. I’m going to keep doing me. And I hope this post inspires you to keep (or start!) doing you.

Let’s take a look at how my entrepreneurial style has evolved over the past few years, shall we?

February 2015, CT Style appearance: I was only comfortable wearing all black at this point. I took a chance and ditched the blazer, but still kept my hair down and straight. I remember thinking these leopard heels were a stretch! Living on the edge, ha!

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March 2015, Good Day Austin appearance: Basically more of the same here. Playing it safe in all black, but desperately wishing I could have done something different with my hair!

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August 2015, Champagne & Stilettos event in Atlanta: Wild child begins to emerge! I think this was the first appearance I wore a bright color. I also opted for leather leggings and an edgier shoe, and I remember feeling super confident this night. I even waved my hair!

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December 2015, Pix 11 News appearance: A platinum ponytail, deep berry lips, and a white blazer. This was my edgiest look yet, and I loved every minute of it! If you watch the clip, you’ll even see how confident I appear on camera because I truly felt like myself. I threw away all the rules and wore what I felt great in.

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March 2016, Photo shoot: Major turning point! I had the honor of being shot by my dear friend and amazingly talented photographer, Angelica Glass. This was the “gateway drug” to my style transformation. Halfway through the shoot Angelica and my bestie/stylist Tara asked if they could take creative control of my look. Let’s just say it inspired a tidal wave of change for me, in more ways than you can imagine. You can more about that shoot here if you’re interested.

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June 2016, PINK HAIR! Dying my hair pink has been life altering! It was something I wanted to do for over 2 years but couldn’t find the courage until very recently. It has hands-down been one of the biggest game changers for me, and totally transformed the way I relate to myself and to my business. It has made me feel more confident and more creative than ever. You can read more about my candy colored transformation here.

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As you can see, my style has changed drastically since first beginning my journey as a full-time H.B.I.C. Leaving my corporate job and living and breathing my passion has ignited a world of change for me, and being able to express that through the way I look is so much fun. If you’ve been struggling with trying to find your fashion groove as a girl boss, then I invite you to take these final thoughts with you:

You can dress as fun and edgy as you want, and still be taken seriously. My business has exploded over the past year, and I basically live in Converse sneakers and SoulCycle gear. When I have to get a little decked out, I do it in a way that feels authentic to me. Even if I think everyone else will look a certain way at a party or a networking event (ex: little black dress, stilettos), I do what feels right for my style. If I’m in the mood to wear a band t-shirt, heels, and leggings, I do it! I’m not a dress girl, so I stopped convincing myself I need to wear dresses. Just. Be. You.

Your career, your rules. We all got into this entrepreneurial world because we wanted control, right? We don’t want dress codes; we want excitement, passion, and creativity. If you can create your own job, you can create your own signature look to go along with it. Own it!

Owning your personal style will make you more confident in every area of your life. When you look good, you feel good. And when you wear things that make you feel unstoppable, it will show up in the way you live, love, and work. I’ve never felt like more of a bad ass than I do now. I work out harder, I write more passionately, and I feel sexier than ever. When you’re trying to fit into a box, none of those things are possible.

Your vibe attracts your tribe. Now that I finally look the way I feel inside, I have been attracting THE most amazing people into my world! From readers, to other kick-ass girl bosses, to inspiring people who make my world better, they’re all showing up. Your style introduces you before you even speak, so make sure you’re presenting the most real you possible. The right clients and people will find you and love you, for you (tattoos, pink hair, leggings, and all!).

 

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Showing 17 comments
  • Brittnae
    Reply

    That photoshoot seriously was a game changer… and this blog maybe a little inspiration for something crazy over here !!! EEEK

    • caraalwill
      Reply

      YES!! Can’t wait to see! XO

    • Emily B.
      Reply

      Love this!! I have been trying to figure out my own style as a entrepreneuress, mother and just a woman! Being 27 isn’t so fun and exciting as people who’ve watched it come and go think. I feel I am faced with the most pressure right now trying to figure out what my style is as I both lose weight and grow out of all the “college” age outfits and into a woman of the world. Haha! So thank you for being so BOLD and taking us along on your journey because it has been the kick in the ass I needed to own my style and rock it!! (Leggings, band t-shirts and all) <3

  • Heather
    Reply

    Love this! My style is something I take a lot of pride in and love expressing more of who I am by what I wear. Love seeing how your style has evolved and it’s definitely empowering to see you do YOU! xo

    • caraalwill
      Reply

      Thanks babe!

  • Danette
    Reply

    Thank out for sharing….Love seeing the evolution of Cara!

    • caraalwill
      Reply

      Aw, thanks Danette! XO

  • Christina
    Reply

    Love this. Loved seeing your evolution. I could tell in the pictures of you rocking your true style how confident & happy you were in your smile. I work for a company that went from business casual to wear whatever you want (within dress code guidelines…of course). I have always avoided showing my true style at work b/c of the comments from the peanut gallery. This blog inspired me to say fuck it I’m going to be me & rock my style xoxo

    • caraalwill
      Reply

      Thank you!! xo

  • Nekea Littlejohn
    Reply

    You’re so inspiring!!! Just shows that facing your fears and being yourself is always the way to go!! I always made an effort to “dress down” to avoid the “where are you going?” or “wow you’re really dressed up!” comments and found myself being uncomfortable all night (and still getting those comments lol). I learned not to feel bad about wearing those sequins leggings or sheer top if I wanted to. I learned that life is so much easier when I’m being my true authentic self. xoxo

    • caraalwill
      Reply

      AMEN to that!! xoxo

  • Brittany Lawson
    Reply

    Love this article! As someone who has always struggled with confidence this article really hit home for me. Thank you so much for the inspiration!

    • caraalwill
      Reply

      You are so welcome, Brittany! Happy it helped! XO

  • Elizabeth
    Reply

    I think you are amazing,and following you along with your shares reminds me why I fell in love with Rhonda Byrnes. Women like you remind me to dig deep within what feels good to the soul, and why it’s so important to “do you”. Thank you! 😘

    • caraalwill
      Reply

      Thank you so much! Mwah!

  • Jessica Wirth
    Reply

    Cara I absolutely adore you, you’ve inspired me. Waiting on another book my dear <3 You've also, with the inspiration ofGretchen Barrocio, helped me start my own blog. Gotta start somewhere right? 😉
    wirthitdesigns.blogspot.com
    XOXOX

    • caraalwill
      Reply

      Thank you!! So proud of you! xoxox

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