Casual CEO Style For Men: 4 Must-Haves For Leadership Roles

September 13, 2021

Many offices now have casual dress codes, but figuring out how to dress as a casual CEO can be complicated.

Traditional office attire (like a suit and tie) might look stiff or out of place. Whereas a hoodie and gym shoes probably won’t match your brand as a company leader.

Fortunately, there is a way for CEOs to dress casually and still look put together. In this blog post, I share my 4 must-have clothing items for casual CEO attire.

Polo Shirts In Core Colors

A White Polo Shirt Is A Staple Of Casual CEO Style For Men

Photo Credit: Mr. Porter

Polo shirts are a great addition to any casual CEO closet. They are less formal than a button-down and are more polished than a regular t-shirt. This makes them the perfect option for men working in a casual office.

Make sure to focus on core colors like black, gray, navy, and white.

By focusing on core colors, your polo shirts can be dressed up or down depending on what you wear. Try wearing a polo shirt under a blazer for a professional look or under a jacket at informal events (more on this below).

For the workplace, avoid wearing polo shirts in pastels or athletic fabrics. Pastels often look informal and they don’t create the powerful image most CEOs are looking for. Similarly, shirts made from sports materials can read as too casual and send the message that you would rather be somewhere else.

Drawstring Pants In High-Quality Materials


Photo Credit: Nordstrom

As a men’s image consultant, this is one of my favorite pieces for a casual CEO. This style of pant looks put together, without looking stiff.

When choosing drawstring pants, consider the style of the piece and the material. Your drawstring pants should look sharp and sophisticated. I recommend a wool or synthetic blend for your go-to’s because they’ll keep their shape throughout the day and look put together.

Details such as pockets, subtle patterns, and a structured fit help make a comfortable pair of drawstring pants look tailored and stylish.

You should also make sure that the material is appropriate for the office. In the summer, try this men’s pant style in a lighter material like a linen blend. During the winter, a warmer material such as wool is a good option.

Stay away from pants that look like they could be sweatpants. As a leader, you want to show that you have a vision and a plan, but sweatpants make you seem unsure about what that vision is. In short, sweatpants can look like a lack of planning and intention.

Invest in Tailored Outerwear

Lardini Herringbone Wool Overcoat For Male CEOs Casual Style

Photo Credit: Mr. Porter

Choosing the right outerwear is your next step. When working with my male styling clients, I often recommend investing in a high-quality outerwear piece.

Outerwear is a good way to add interest and style to your look. For example, a blazer, leather jacket, or bomber jacket can take your outfit to the next level.

After you find a jacket be sure to have it tailored, especially the sleeves (which are typically too long for most). The right fit will make a huge difference in your personal brand.

From there, you can easily mix and match it with the rest of your closet. This means you can combine your clothes without wasting time or worrying if it looks good.

To start, try pairing a jacket with a polo in a core color. Sundar Pichai, CEO of Google and Alphabet, is a great example of how to wear a jacket in a casual, yet professional way.

Modern And Sleek Shoes


Photo Credit: Mr. Porter

A modern sneaker is a must-have for casual CEO attire. Your shoes help pull your entire look together.

Look for a sneaker that is modern and casual, while maintaining a professional edge. Leather or suede are both elevated materials for your sneakers. Choosing sneakers in a core color will ensure that they match with the rest of your wardrobe.

But you should be careful here.

A common mistake I see is men wearing gym shoes to the office. Keep your gym shoes for workouts and try a minimal day sneaker instead. The navy shoes in the photo above are a good example of what to look for in a day sneaker. On the other hand, the sneakers below are for the gym and won’t enhance your professional image.

Nike Gym Shoes Are Not Appropriate For Casual Male CEO Attire

Example of what a gym shoe looks like- keep these for the gym only.

Photo Credit: Nike

What should male CEOs wear?

Focus on building a wardrobe of tailored essentials in core colors. With the right strategy, you can create a closet that allows you to look like the leader you are.

For more about men’s style, read my Executive Image Style Guide for men.

To build your professional brand, check out my Virtual Executive Image Consulting service for men. I’ll help you create an executive image that is powerful and competent, yet casual.

About the Author - Cassandra Sethi
About the Author - Cassandra Sethi

Personal Stylist & Image Consultant

Cassandra Sethi is a Personal Stylist and Founder of Next Level Wardrobe, a luxury Personal Styling and Shopping Service that helps successful professionals of all ages and sizes. After working in the fashion industry for over 25 years, she used her expert knowledge to create a proprietary styling system called ‘The Next Level Wardrobe Style System' which guarantees clients more outfits with less items in their closet. NLW has been featured in The Wall Street Journal, The Tamron Hall Show, NY Mag, Huffington Post and more.

*Disclosure: Next Level Wardrobe only recommends products that we’d suggest to our clients or personally wear ourselves. All opinions expressed here are our own. This post may contain affiliate links that at no additional cost to you, Next Level Wardrobe may earn a small commission. Read the full privacy policy here.

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Cassandra Sethi

is a NYC Personal Stylist and Image Consultant. She is the Founder of Next Level Wardrobe and 'The NLW Style System' that guarantees clients more outfits with less items.

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