How a CEO Gets Dressed in the Morning

Catherine Cassidy (Business Heroine Magazine)

As a personal stylist who also stands in the role of CEO, speaker and moderator, I wear many hats, ALL of which are pretty visible.

I have to set the standard for our clients, my employees and the audience. My aim is to inspire those around me to FEEL good in their body and clothes. To want them to want to show up and be seen. I can’t make anyone do that, but I can show them that it’s not scary.

I’ve used my style as an armor in situations where I was completely outside of my comfort zone. Historically, I’m very shy (and I still have bouts of shyness), and I’ve used my style to bolster my confidence. And, ultimately, I’d ease into the situation and stand in my own power.

It’s only in looking back that I have realized it wasn’t the power of the dress/jeans/heels, but what power they allowed me to access.

So, I empower my clients to do the same.

To use their style as a catalyst to step into their power. To OWN the room. To make sure they’re heard and making the impact they’re meant to make.

But it starts with complete confidence in your presence, which includes your style. So, I wanted to share with you how I create an effortless style that communicates a powerful presence, myself, each morning.

(1) Start with MY self

It is incredibly rare that I start my day without doing something to take care of myself FIRST. Typically, I meditate, journal, read. Every other morning I add a quick workout. This takes about 1-2 hours and I still start my work by 8:30/9.

Granted, I don’t have children or a partner to worry about, so I do get to be completely selfish. But, I did start this routine when I was still in a relationship. It’s a matter of committing to YOU first and this is something that doesn’t cost a thing, but pays off in dividends in how you show up.

A big part of presence is in the word – it’s being completely present and grounded. So, to have a powerful presence, it’s important to make sure you’re taking care of yourself, first.

(2) Check the weather

Ideally, I DO do this. Since moving our headquarters to Washington, D.C. from Los Angeles, I have been much better about this step! In LA, it was inevitable that I was inappropriately dressed for the weather, but the variation in temperature usually was moderate. Here in D.C., you can’t do that!

(3) Consider the audience

What am I doing today? How dressy or casual is the audience? How traditional or progressive are they?

While I’m a huge advocate of being YOU in every situation, it’s incredibly important to be mindful of who you’re meeting with. This is especially true when you’re giving a presentation or taking a meeting that could have a big impact on your career.

To be sure that your message gets across and isn’t distracted by what you’re wearing, you do have to defer to their preferences. BUT, you have to keep YOU in the picture as well.

How do you do this?

Be mindful of tailoring and fit. That the skirt isn’t too short, the neckline isn’t too low and the fit isn’t too tight.

You also don’t want to be pulling or fussing with your clothes as that’s just as distracting.

Add a pop of color or a personal accessory. Even if in a masculine setting that requires business formal, add a feminine touch with color, print, accessories, etc.

LET’S BE REAL: Even on days when I’m not going to meet with anyone, I’m still getting dressed in MY style. Those glorious days that I get to stay in one place and focus, I may stay in workout clothes or be really casual, but I’m putting on my completely coordinated and CUTE workout clothes (I seriously can’t help it, it’s just ME!) or my favorite jeans and tee (totally the basis of my style) with a couple of easy accessories.

(4) Pick my shoes

I love a great pair of heels as much as most women, but I can’t wear them every day, especially if I’m working with clients or out shopping.

So, I typically start building my outfit from what shoes I want to wear for the day. Do I get to wear heels? Do I need to do a lot of walking? Is it a moderate amount of walking? Who am I meeting with? How am I getting there.

Sounds like a lot of work, but it takes just a second. I don’t have a HUGE shoe collection, I’m as particular about comfort as I am style, and many of the styles I have can read as neutrals – so they go with anything.

(5) Build up from there

Once I’ve decided on the shoes, I build the outfit from there. The shoes I can and want to wear will dictate which pants, dresses or skirts are best.

It’s so easy to create an outfit with what you have. Everything starts with a base (dress or top + bottom). Then, you add a layer (jacket, sweater, belt) and the accessories (can be the layer).

This is something that can take some time to develop as a skill that is truly effortless, but having a point of reference with a Style Inspiration Board on Pinterest or Lookbook can help you to get there.

(6) Add the finishing touches

It’s easy to throw on a top + bottom or your basic suit and head out the door. But, it’s pretty boring and uninspiring.

Be honest with yourself: How do you feel throughout the day when you get dressed for the sake of getting out the door vs. when you get dressed with intention for the day (typically when you have a really big meeting)?

So, what is different about those days? Yep! The finishing touches!

That means adding accessories, even if they’re simple. They can be small earrings or a drop necklace. Maybe it’s the same ring you wear every day. (Hint: This makes it easy and becomes a statement of your style.)

(7) ROCK IT!

Typically, this all takes me less than 5 minutes of time actually getting dressed. Steps 1 – 4 I’ve thought through while doing my makeup + hair. And it ALL comes down to wanting to FEEL GOOD. I may be a personal stylist, but a lot of my power comes from the fact that I’m actually not trying that hard with what I’m wearing. I’m having fun and I’m just being ME. And showing up 100%.


style comes down to wanting to feel good - Catherine Cassidy

Business Heroine Magazine


We’d love to hear from YOU…

How do you get dressed in the morning? What are your favorite ways to feel great in your style? Leave your answer in the comments below!




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