How to Dress Like a Casual CEO

Ready for a shortcut to great CEO style? Apply to work with NLW.

If you’re finding yourself at a crossroad between dressing casually yet professionally- you aren’t alone. Many of my professional clients CEOs are too.

But there’s a way to dress casually and still command respect, leave a memorable impression and lead your team.

Read on for five casual CEO looks that work in and out of the office.

CEO on the Go

Female CEO Wearing A Business Suit In A Casual Style

Photo Credit: @LaurenCaruso_

Many of my clients are on the go- and they want their shoes to keep up with them, so flats it is!

Nowadays sneakers are an acceptable type of footwear for casual offices. And that doesn’t mean your gym sneakers (yes there is a difference between gym vs day sneaker)

Wearing a sophisticated daytime minimal sneaker with a blazer and good-fitting straight-leg jeans is a look that is put together and comfortable. You can also wear them with dresses, trousers, skirts- you can’t go wrong!

Want to try this but not sure what color to buy? Go for a white or grey pair as your first sneaker investment. With those core colors, you’ll get a lot of wear out of them.

The Elevated T-shirt

A Female CEO Wearing An Elevated T-shirt As Part Of Casual CEO Attire

Photo Credit: Pinterest

Now while a t-shirt sounds a bit too casual for CEO attire, it’s actually an essential that your office wardrobe needs.

Don’t be turned off by the word t-shirt. A great fitting t-shirt is the most indispensable and versatile piece that can be dressed up or down for any occasion.

You can layer a blazer over your t-shirt or even a sweater vest for that CEO style.

A good fitting t-shirt looks great with any type of bottom whether they are jeans, tailored trousers, or pencil skirts.

This type of look says you’re in charge and in style.

The Office Sweater

Woman Wearing An Office Sweater From Her Casual CEO Wardrobe

Photo Credit:@ellenclaesson

Does the office draft make you shiver sometimes?

That’s where the perfect fitting sweater comes in. Comfortable and chic are two things everyone loves and works especially great in the office.

In any event, a good fitted sweater that goes with any bottom is a lifesaver when the unexpected occurs. They’re easy, comfy, and most importantly, casual for CEO style.

An Easy Going Dress

Woman CEO Wearing A Dress From Her Business Casual Attire

Photo Credit: @karenbritchick

A dress that you can pair with heels or sneakers is a must-have closet essential for casual CEO attire.

If you find yourself not being able to spend a ton of time getting dressed in the morning, what better way to get out the door faster than a casual, easy dress and a pair of neutral sneakers.

It’s time-effective and almost fool-proof. Be mindful of your dress length even if the office space is casual, you still want to be appropriate- go for knee length as a good rule of thumb.

Pair the outfit with some minimal jewelry like a few rings, earrings, and a necklace and you’ll have an effortless, timeless look.

Straight Leg Jeans

Female CEO Dressed In Straight Leg Jeans

Photo Credit: @brittanyxavier

We’ve all erased the skinny jeans trend from our memories and opted for a more sleek and figure complementary way.

You could pair your straight-leg jeans with absolutely any top and it’ll always look good.

For the office- opt for a casual, loose-fitting top or any elevated basic to look and feel polished to casual perfection.

Jeans have always made any outfit a bit more casual, and all my clients love a good pair of straight-leg jeans and know that it’ll be a closet essential forever.


Need a little more help pulling off casual CEO style? Check out my Executive Image Consulting services.

More Posts Related to CEO Style

Picture of Cassandra Sethi

Cassandra Sethi is a NYC Personal Stylist and Image Consultant. After working over 15 years in the Fashion Industry, most recently as a Senior Buyer for Equinox, she created her business, Next Level Wardrobe – a luxury personal shopping service for successful professionals.

Next Level Wardrobe has been featured in Wall Street Journal, Today and CNN. See here.


For immediate help to upgrade your work style (virtually or in person), use this link to apply for a style consultation.

To receive my complimentary guide, 3 Items You Need In Your Closet Today, click here to put in your name and email.

Apply for a style consultation for immediate help to upgrade your style

Download my complimentary guide, 3 Items You Need In Your Closet Today

Next Level Wardrobe
[email protected]
Follow Me:
Newsletter Sign Up: