Cultivating Confidence Through Your Style

Catherine Cassidy (Business Heroine Magazine)

Last week I hosted an intimate gathering of smart, successful and beautiful women to discuss style. This salon setting was intended to be very conversational so we could talk about what it really means to ‘dress for success’ in today’s professional world.

Of course, there is no easy answer for women.

There is a constant struggle, a tug of war between what is considered acceptable in any given situation.

The questions seem endless:

  • Does it look professional enough?
  • Am I showing too many curves? How do I hide my chest?
  • Does this come off too sexy and not serious enough?  Is this TOO serious?
  • Is it too much color? Not enough?
  • Is this appropriate?

The results of this can be draining, leaving women feeling uninspired and ready to settle for whatever feels ‘safe’.  Usually this means something non-descript that probably doesn’t fit or convey confidence.

Unfortunately, we don’t have the luxury of putting on a custom made suit and being ‘appropriate’ in a professional setting. The fact is that it’s incredibly hard for women to find suits that fit well. Instead, we have to be ‘professional’ in a boxy jacket that doesn’t do anything for our curves.

But, we do that because we are wary of drawing the wrong attention to ourselves. We want to be seen as smart and savvy, not just pretty.

But to downplay any part of ourselves is to self-sabotage our success because we’re not showing up 100%. We hide a little bit.

My intention is for you to own your entire presence — whatever your size, shape, color, hair, etc.

You need to respect yourself as much as your environment and audience. And by showing up as 100% YOU, you inspire those around you to do the same.

I have witnessed with ALL of the women who have worked with me that their style is a catalyst in their confidence and so, ultimately, in their success. They start landing more speaking opportunities, bigger clients, more dates, perhaps even a HUSBAND … all because they invested in themselves through style. (Obviously, they also did the follow up work to create those opportunities, but it indeed started with STYLE.)

If you’re ready to have complete confidence in your presence and style, here are a few ways that you can own the room:

Know and Love your Body

When I’m working with a client, the majority of our initial work is around how the clothes they currently have fit. Most women are not buying the right size, but it’s usually because they’re going up a size to have room in their clothes, thinking that means they fit.

But, when you buy clothes too big, they make you look bigger than you are.

I do understand that you don’t want clothes too tight, either. Especially if it highlights some of your assets that you’d rather downplay in a professional setting.

I get it – I have curves myself. It’s taken me a LONG time to love my body. Over the years, they’ve gotten a lot of unwanted attention which made me want to hide them just like many of our clients.

I now love my curves for 2 reasons:

→ Like many women, I will gain and lose weight and have to adjust what I wear. Fortunately, I know how to flatter my figure whatever size I am at the moment so I can always feel confident in my presence and style.

→ I dress to flatter my curves, but can strategically downplay them when I want.

One of my favorite tricks is to balance a fitted item (such as a pencil skirt or skinny jeans) with something that is close to the body, but not tight. Sometimes, I’ll add a jacket and/or a belt so I maintain a feminine figure without being so overt with my curves.

Additionally, when I do want to tap into my sexy side, I can and do play up my curves.

One thing I want to point out – dressing your body is quite nuanced. This is why it can be so frustrating. Especially when your body keeps changing throughout your life.

This is why ‘dressing your body’ is a major focus in my work. Most stylists speak to 5 different body types, but I tend to find that most clients don’t perfectly fit into one ‘type.’

What you do want to focus on for dressing your body, regardless of your shape are the following:

  1. Focus on Fit (no bunching or pulling)
  2. Mind your waist (either create it or highlight it)
  3. Balance your proportions (if you have volume on top, it should be fitted on bottom and vice versa)

Knowing how to dress your body regardless of your size is powerful. It allows you to feel confident and beautiful whether you gain or lose weight. That way, you’ll always be perfectly YOU.

MY CHALLENGE TO YOU – try on all those black pants and toss the ones that you don’t LOVE (aka they don’t bunch or pull or gap).


Add a Pop of Color

Sometimes we have to dip our toe into the water before we jump all in … and adding a pop of color will do that for you with your style.

Owning your presence and power is about being SEEN. Black is safe, neutrals are easy, but color will make you stand out. It is also a very powerful element for conveying your message and intention.

It’s also the easiest first step.

You can stick to your neutral wardrobe and add a pop of color through an accessory – a scarf, necklace, earrings or even a simple ring.

If you’re feeling bold, mix colors! This is something we do a LOT with our clients. I LOVE playing with color – it adds personality and also highlights how style savvy you are!

You can start with this quick tip to play with how people respond to you at work, at the coffee shop and out and about with friends. I bet you’ll be getting a lot of compliments and starting some interesting conversations … and you never know where a new connection can lead.



Last but absolutely not least, you have to do you.

I am SO not into trends. I may be slightly aware of them, but they don’t matter much to me for our clients. I may take advantage of some if they happen to flatter a client’s style and/or body type, but the thing with trends these days … is that there aren’t any true new trends.

We actually are in a time where we can do almost whatever we want from a sartorial point of view. We see almost every decade’s influence on the streets (even the 90’s grunge, unfortunately) and every pant style is now a staple in the stores (straight, skinny, trouser, bootcut), so you can find the pant that fits your body.

What I want you to think about is where you may be sacrificing YOU for the sake of the environment you’re in. This can be really tricky in a conservative environment, but also all the more important.

I do want to highlight that it is definitely important to be mindful of your audience if you want to make a powerful and positive impressing, but it’s just as important to show up as YOU.

If you try to adjust your style to simply fit in to the situation, you’ll communicate that you’re passive, not that you’re powerful.

Why wouldn’t you want to control the message you’re sending about yourself?

For instance, if you’re edgy, but you work in a very conservative environment, you need to find a way to bring your edge into your style. This is possible and can be subtle through accessories, details on your clothes, shoes, etc. You can ease your way into adding edge in a way that honors you as much as it honors what is appropriate for the occasion.

And that edginess to your style could lead to creating a literal edge for yourself at work.


Catherine Cassidy (Business Heroine Magazine)

Business Heroine Magazine


We’d love to hear from YOU…

Does your style make you feel confident? Which of these tips could you try to feel more powerful in your clothes? Leave your answer in the comments below! 





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