Dress Like the CEO You Want to Be: How To Improve Your Style to Match Your Ambitions

Dress for the job you want, not the one you have. It's a cliche because it's true!

I would add: dress for the job you have, and if you aren't already, it's never too late to begin again.

Here's a secret: dressing like a CEO isn't just about power suits and high heels. It's about crafting an image that exudes confidence, competence, and charisma and feels like you.

What Does a CEO and Executive Leader Dress Like?

Whether you're a corporate employee, a tech entrepreneur, or a marketing maven, your clothes should be an extension of your professional prowess -- with the addition of YOU to make it feel authentic and comfortable.

Like my client Laura who wanted to look like the Partner she was, and not stumble through the fitting room like she has for years while building her career.

female woman executive ceo style before and after

Styling Client Transformation

After her promotion, Laura wanted to look like a firm Partner. For years while building her career, fumbled through fitting rooms and wanted to dress the part once and for all.

Think about the movers and shakers in your industry.

They're not just well-dressed; they're walking statements of their personal brand.

Your goal? To develop a wardrobe that reflects your unique identity while aligning with the professional standards of your goals and field.

Choose the right ensemble and you'll be commanding any room knowing you look gooooood .

  1. Start with the Basics: Tailoring and Fit

The foundation of any power outfit is impeccable fit.

A well-tailored suit or beautifully fitting dress can make a world of difference because it's not just about looking good; it’s about feeling good.

As a stylist and image consultant, I can't stress enough the importance of investing in tailoring and alterations for a better fit. Check out the difference with a basic outfit here.

When you’re clothes fit like a glove, your confidence soars, and you stand taller. (Amy Cuddy proved why that matters) and it shows -- inside and outside the office.

Male Styling Client: Before & After

Our client was leading a team as a partner in his accounting firm and wearing badly fitting men's dress shirts trying toe easily fit into his company’s Smart Casual dress code.

His recent weight changes made it difficult to find clothes that fit well and were comfortable.

He wanted to feel stylish, not like a middle-aged CPA, and have fun - safely - with fashion.

He looks fantastic!

2. Wearing your Right Colors to Complement and Dress More Stylishly

Color analysis isn’t just fluff; it’s a strategic tool in your style arsenal.

That's why we offer Color Analysis as a part of our Full Service Styling because it makes a difference (to those who choose to use it)!

Executives are often seen in power colors like navy, black, and grey, but don’t be afraid to add a splash of personality with bolder colors and patterns.

The key is balance – you want to stand out for all the right reasons, but also wear what you like, regardless if it’s “right” or not. Find the colors that suit you, enhancing your natural features and conveying your personal brand, and then decide if it matters to you and your goals.

3. How to Accessorize Like a Boss (or Not at All)

Sophisticated accessories are the cherry on top of your CEO look.

Choose pieces that are understated yet impactful. A sleek watch, a statement bag, a polished belt, a stack of rings are all easily accessible accessories. The goal is to enhance, not overwhelm yourself or your outfit.

When overwhelmed by choices, choose the most elegant and polished version available. Even then, accessories aren't necessary for each outfit.

4. How to Not Wear Accessories

When the rest of your closet is still a hot mess.

First things, first. Necklaces and watches don't matter as much if your clothes don't fit properly after a body change. When you have outfits and clothes you're excited to wear you can work on exploring accessories and experimenting.

5. What Shoes to wear when working as a leader or CEO

Shoes can literally and figuratively elevate your look. Plus, they're a subtle indicator of your attention to detail – a trait every successful CEO possesses.

Women don't have to wear heels, and men don't have to wear dress shoes, but it all comes down to preferences and expectations in your offices.

The most important part of shoes is the quality. They shouldn't look tired or overworn, and you're best with real leathers and suedes. These materials look luxe and polished, regardless if it's a high heel, a loafer, or a sneaker.

6. Embrace and Enhance your Fashion Sense

Don't be afraid to create a wardrobe that positions you as a leader in your industry while also reflecting your inner awesomeness.

You can find more information about how to do that here!

For example, want to incorporate a trendy piece? Go for it, as long as it aligns with your overall look and image goals. The best-dressed leaders are those who stay true to themselves while maintaining a professional edge.

7. Invest in Quality Over Quantity

Building a CEO-worthy wardrobe means making smart, strategic choices.

Invest in high-quality pieces that will stand the test of time, both in terms of style and durability. Think of it as a savvy business decision for your personal brand.

8. Seek Expert Advice by Working with a Stylist

Feeling overwhelmed and don't have the time to figure it out? That's where a stylist comes in.

You might worry that working with a stylist means you'll look like everyone else who works with a stylist -- but a good stylist (ahem) will help you create a wardrobe that projects a strong image while still staying true to you.

Learn more About Us

See more Client Transformations.

P.S. Let’s get you dressed like the CEO you're destined to be. Book a call and let's make your style speak volumes about your professional ambitions. After all, in the bustling streets of the corporate world, your style is your silent yet most persuasive business card.