Lately, I’ve been thinking a lot about how we dress for confidence at work. How we can show our true identities at work beyond the traditional corporate colour palette of grey, black and white.  

So, I decided to have a chat with Jessie Jolly, a Perth-based personal stylist, image consultant and public speaker who empowers her clients to discover their personal style and dress with confidence. 

Through her own experience and a keen eye for personal style, Jessie helps her clients let go of limiting beliefs that keep them stuck in old ways of dressing, whilst teaching them HOW to think differently about their own bodies and clothes. Jessie works with a number of career-focused women to help them show up feeling confident and ready to take charge in their careers with their own unique professional style and flair. 

Honestly, my conversation with Jessie was GREAT! I felt like I had my own personal stylist on speed dial! We spoke about how we look, impacts how we feel, which ultimately impacts HOW we show up. We spoke about how you can bring your true identity to work through how you dress. AND we spoke about how dressing with confidence can come with any budget. 

Check out a summary of our conversation below! 

How Do You Let Go of the Old – And Ultimately, Make Way for the New?

Do you have a wardrobe full of clothes, but still feel like you’ve got absolutely nothing to wear?

So many of us can resonate with this. We have clothes that we no longer wear but still keep in our wardrobes in the hope that one day we will feel beautiful/slim/toned/confident enough to wear them - even when we know deep down we never will.

Jessie calls these “guilt clothes”. 

“These are clothes that tie to a part of our identity or a part of our body that we used to appreciate, and they just sit in your wardrobe taking up space. However, they are essentially just little pieces of guilt laying in there, not making you feel good and not making getting dressed any easier,” Jessie explains. 

Her suggestion? Clear them out and do a wardrobe detox. You’ll feel lighter. 

Let go of the old so you can make way for the new. To do that, here’s a few questions Jessie suggests you ask yourself: 

“What direction do you want to take your style?” and “Why are these pieces so important?” 

They’re not just clothes, Jessie explains, but they hold a piece of your identity and that’s why you’re holding on to it. Was it a fun freedom that you felt when you were wearing it? Was it a time when you were super confident and feeling really sexy? It’s crucial that you identify that part of your identity that’s really important to you. Then, take that feeling back and find ways to start implementing that in your future wardrobe choices in a way that makes sense for the woman who you’re trying to step into. 

To help draw out what you need and what you’re aspiring to, Jessie suggests considering these questions:

  1. Are you moving or changing roles? Or, are you looking to change roles? If you’re looking to change roles (or are changing roles), then you want to think about what is the identity you’re looking to share - what message is it that you want to send out to the world? If you’re looking to get advanced in the position that you’re currently in, perhaps you want to start making small tweaks so that you can be noticed. 
  1. Who are you? And no, I’m not talking about the roles you play  – not about the fact that you’re a career woman, a mother, friend, daughter etc – but who are you, really? Would you describe yourself as someone who’s fun-loving and adventurous? Or, maybe someone who’s more quiet and serene? Now, imagine how that would look in your clothes. What would you wear if you want to be perceived for who you are? 

Identify Your Comfort Zone 

For women who work in the corporate world, it’s easy to feel lost amid the uniform and classic workplace outfits (maybe slightly less so in a Covid-world, but you get the drift!). So, how do you deal with workplace dress code boundaries? How do you deal with certain expectations with what to wear in the workplace? 

Many women are often scared to step out and be noticed; it’s almost like we want to just blend with what is acceptable.

But, the thing is: you can “blend” and still be comfortable and confident with what you’re wearing – it’s all a matter of identifying your comfort zone and working out what you’re comfortable with. 

For example, for corporate women, there’s a lot of really beautiful brands and workwear available now outside the classic black pants, white shirt, and black blazer. You’ve got a lot of options to choose from. Jessie says, “Don’t be afraid to mix it up!” Wear a colourful shirt or even one with a pattern! If you still feel like yourself and if you’re dressing the way you want to dress, then do it. Have to wear a uniform for work? Try to incorporate your own personal style into it – wear a scarf, wear your hair up in a ponytail with some earrings you love – add a touch of YOUR ‘signature look’ into your outfit. 

When You Feel Good, You’re More Confident

We all have our own personal styles and preferences, but what’s important is this: Dress how you want to dress; but dress in a way that makes you FEEL good. Because when you feel good, you’re more confident, and when you’re more confident, you’re more likely to lean in, take risks, and step forward.

When you start dressing in a way that makes you feel good; when you start wearing clothes that you actually like, you’ll be able to see a difference in yourself. It’s not just about finding new clothes – it’s about seeing yourself differently and appreciating who YOU are, how your body looks, and accepting that and then allowing yourself to shine in that space. 

You can listen to my full conversation with Jessie Jolly here.

Need some support with your career journey? Book a call in my calendar HERE.