Tech CEO Sneakers Do’s and Don’ts

August 23, 2022

In the world of business fashion, Silicon Valley occupies a unique space. The tech CEO sneaker takes center stage as a status symbol.

From Tim Cook to Elon Musk, the top names in the industry forgo normal business wear for streetwear. So how do you pull-off this understated look?

As an experienced stylist and image consultant with clients working for Google, Amazon, and other household names, I’ve seen it all. I know what you can actually wear to the office and what only works in Silicon Valley, the TV show.

Read on for my realistic tips on adding tech CEO sneakers to your closet.

Tech CEO Sneakers: Our 3 Do’s

1. Buy one light colored sneaker and one dark colored sneaker

Instead of splurging on flashy shoes that’ll go out of style in a month, lean into a pair that you’ll get the maximum outfits out of.

My recommendation? Buy one light-colored pair and one dark-colored pair of sneakers. For a dark color, reach for black or dark brown. For light tones you can’t go wrong with white or light gray.

These two colors give you ultimate versatility. No matter what time of year or what occasion, you’re ready to go.


Photo Credit: Koio

For example, say you’ve got a typical day at the office. Opt for light colors so you feel approachable to your team, like this white perforated pair from Koio.

Or maybe you’re meeting with investors. Give your pitch credibility with a black pair of leather sneakers. The possibilities are endless.

2. Wear your sneakers for most occasions

Many of our clients draw a strict line between formal and casual shoes. They think they have to stick to dress shoes for every formal event and save their sneakers for the weekends.

Those rules are a thing of the past.

You can wear sneakers to about 95% of occasions these days. From day to day office wear to your weekend usual, these shoes are an essential part of your outfit lineup. Especially if we’re breaking down Tech CEO style in Silicon Valley.

The only time I would skip the sneaks is for true special occasions. Think an upscale dinner, board meetings, or any other event where you have to be more traditional or “conservative”. In those cases, reach for your dress shoes instead.

Photo Credit: To Boot

Personally, I love styling my male clients looking for formal shoes in To Boot. They carry everything from boots to dress shoes like these plain toe bluchers that will go with any suit.

3. Keep your sneakers in good condition

What’s the point in investing in a great pair of sneakers if you don’t take care of them?

Though tech CEO sneakers are meant to give a carefree look, they’re and item that will require some maintenance. Avoid crossing over into sloppy territory by keeping your sneakers clean.

Don’t worry. I’m not about to tell you to build a tedious routine or polish your kicks on a daily basis.

It can be as simple as keeping a cloth by your shoes. That way you can give them a quick once-over before you take them off (seriously it will take less than a minute and the ROI is huge!)

If you have shoes needing a more serious clean, try out this sneaker eraser. I’ve personally used this, along with my husband and many NLW clients- it’s amazing!

Now that you have the basics of wearing tech CEO sneakers, let’s get into what to avoid.

Tech CEO Sneakers: Our 3 Don’ts

1. Don’t wear your gym sneakers as day shoes

One of the biggest reasons clients hesitate to embrace sneakers as the best office shoes for CEOs is because they think these shoes are too casual. Some might even think we’re suggesting wearing the same shoes you’d wear to the gym as workwear.

This is a hard no.

I know it’s easy to bucket all your sneakers together as athletic wear. But just because a shoe could be used for exercise doesn’t mean you should.

So what makes gym shoes different from daytime shoes?

Dont Wear Gym Shoes Like Nike SuperReps During The Day When Dressing As A Tach CEO

Photo Credit: Nike

Gym sneakers are function first. They often have performance features such as thick, spring soles or grippy treads. They look decidedly less sophisticated than day shoes because they don’t have to be. You’re also more likely to see vibrant colors and designs with gym sneakers ( we’ll talk more about this later).

Cole Haan Slip On Black Leather Tech CEO Sneakers For Daytime

Photo Credit: Cole Haan

A daytime shoe is more simple, elevated, and subtle. You might choose an option with high quality fabrication like polished leather or suede, or keep it lowkey with canvas. There are many options now when it comes to a daytime sneaker- with laces or slip on, various fabrictions and textures. And the good news is many of them look GREAT!

The bottom line?

These tech CEO sneakers are just as wearable as gym shoes but they look ten times better.

2. Please don’t wear Allbirds

If you want to put some real effort into your style, step 1 is to donate your Allbirds ASAP.

You heard that right.

I don’t care how comfortable they are or if you got them for free. Please donate them immediately.

If you’ve been following me on Instagram you know I’m not a fan of Allbirds. Why? They just don’t look good! And I KNOW that there are shoes out there that are way more comfortable and look even better.

Trust me. Life is too short to wear boring wool runners.

3. Don’t give into the hype

Tech CEOs Screenshot Shopping For Trendy Colorful Sneakers

It’s tempting to scroll through listicles about the sneakers worn by tech executives and think that the trendy path is the way to achieve this look.

But here’s the truth. Wearing over the top kicks is the fastest way to look more like a teenager than a CEO.

NLW Tech CEO Client Wearing Stylist Loafers And Stylist Sneakers

NLW Client. A great pair of sneakers can take your look from frumpy to put together

Want to switch up your Tech CEO sneaker collection? Go for tonal colors such as light brown or light gray.

Consider something like the pair in the above photo. I recommended these to one of my clients who needed a more updated take on business casual. The blueish gray looks less stuff than black while still grounding his look in professional neutrals.

Looking for help upgrading your CEO style? Start off on the right foot with Next Level Wardrobe’s executive image consulting service. With our help you’ll easily learn how to communicate your brand and leadership through your clothing choices.

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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