For professional CEOs, your personal style and image are hugely important. It can take your business success and networking to new heights or hold you back.
That’s why it’s worth investing the time and energy into finding the right wardrobe for you and your lifestyle. But how?
As NYC image consultants, we often get asked, “How do CEOs dress?” or “What should a female CEO wear?”
Instead of telling you, we’re going to show you.
We’ve rounded up the seven best-dressed female NYC CEOs we look to for fashion inspiration.
Now, we know what some of you are thinking: Great. Unattainable red carpet photos. But I don’t look like that!
Guess what? No one does! It’s easy to get intimidated looking at paparazzi photos or edited IG posts and think you can’t cut it. But when you learn the principles of HOW and WHY an outfit works, all of that melts away.
Instead, you’re able to take these photos as inspiration and make them work for your own life.
That’s what we’re doing today. We’ve gathered seven women of different shapes and sizes with diverse fashion tastes and we’re breaking down:
- What their style is
- How it works
Let’s dive in!
Table of Contents
Polished with Pops of Personality: Blake Lively
So many women struggle with looking put-together and professional without losing their personality. There’s a lot of outdated, bad advice out there that says dressing like a CEO means bland suits and saying no to color.
But Blake Lively is a walking masterclass in how dressing well and boldly can go hand in hand.
Whether the actress and Betty Buzz founder is wearing a red carpet-look or grabbing dinner with famous friends, she’s never a wallflower.
She loves patterns, prints, bold textures, and of course, color. But, it always looks purposeful.
Take this all-pink luxe look she wore to a recent Barbie event. There’s nothing quiet about this electric and rosy look. But it doesn’t look messy or even tacky.
Because even though her color choice is loud, her look is simple. She makes a statement with her glam styling and neon color palette. But she doesn’t overdo it with a pattern or crowded accessories.
The textured feather skirt keeps the fun going, but her shoes are simple pointed heels that let her legs do the talking. She ties the look together with a long trenchcoat with no additional detailing to keep things looking clean and feeling cozy.
Nope, this isn’t a look you’d wear to the office. But you can take away these lessons:
- Make a monochromatic statement! Choose one bold, pop of color and wear it from head to toe.
- Keep your accessories and layers simple. Wear one statement piece, not 5. If you’re going bold, let one piece take the spotlight.
- Level-up with textures. From the silky satin of her gloves contrasting with the fuzzy feathers of her skirt, this look is advanced styling personified.
The Modern Leader’s Look: Vanessa Kingori
It’s no surprise that someone who heads up Conde Nast would have great style, but it’s something else to see what they really wear.
This look was from an exhibition event, and while the neckline certainly wouldn’t work for most workplaces, the modern and polished styling does.
Kingori’s outfit is an example of the new modern way of dressing. Notice details like clean, simple silhouettes with updated tailoring. The ensemble fits her figure but adds extra drama and length with the wide-leg, for example.
She keeps her color palette simple, and her hair and makeup relatively paired back. She knows that the neckline and shape of the outfit speaks for itself.
If this look speaks to you, here are some ways to pull it off on your own:
- Prioritize fit. All the bells and whistles in the world don’t matter if something doesn’t fit you right. Seek out high-quality basics that flatter your shape instead of settling for “good enough” or whatever’s on sale.
- Never underestimate neutrals. If you know the NLW Style System, you know we LOVE core colors. That’s because black, white, grey, and navy blue go with everything and never go out of style. Always make sure you have your wardrobe basics in core colors before moving to statement pieces.
- Pick one detail and let it shine. Just like we said with Blake Lively’s look, if you wear a unique or statement piece, don’t overdo it. Find a sweater with an interesting neckline or a belted detail. Then, keep everything else low-key.
Sexy and Sophisticated CEO Style: Eva Longoria
Once known mainly for her Desperate Housewives role, Eva Longoria has achieved CEO status as a producer, director, and entrepreneur.
Throughout her different ventures, however, she’s never lost her characteristic sense of style.
Sexy and sophisticated, Longoria shows female CEOs how they can play with trends, stay timeless, and show off their femininity while taking charge.
Take her look above for example. From the sequin top to the jewelry to the bold red lip, there’s no questioning that she’s in touch with her glamorous side.
But she keeps the outfit timeless with her simple black and white color palette, accented by the textured checkered jacket.
This shows that you can have fun with your outfits while still looking modern and sleek.
Another reason why this outfit works so well? The tailoring. If you didn’t know, Eva Longoria is 5’1” but no part of her outfit looks baggy or ill-fitting. She lengthens her silhouette with wide-leg pants that sit right at her waist instead of too high or low.
So what are the takeaways here?
- Think about your proportions. Anyone can wear any silhouette or style. All it takes is balancing out one piece with another. Eva went for a wider-leg pant, so she balanced it with a slim-fitting top.
- Don’t be afraid of femininity. You can be just as strong of a leader in a power dress as you are in a power suit. Wear those sequins or that bright red lip with pride to your next board meeting. Again, just pair it back to wardrobe staples or classic core colors.
The Effortless Corporate Closet: Raissa Gerona
If you’ve heard of major e-commerce companies Revolve and FWRD, then you know Raissa Gerona’s work. She’s the chief brand officer for these sites, handling everything from marketing messaging to curating collections.
She’s a busy woman whose job requires her to always look at the top of her game. That means she needs to dress impeccably, but easily.
That’s why we love to reference her outfits for effortless, easier-than-they-look outfits.
Take this ensemble she wore for Vogue Philippines for example. She looks cool, casual, and contemporary. Not overdressed or under, this look fits any type of dress code.
The key here is the monochrome color palette, great fit, and clever outfitting.
To recreate this one and done look yourself, follow these principles:
- Pick a color and stick to it. Raissa goes with head-to-toe brown for an outfit that automatically goes together without much fuss. She keeps her turtle neck and bottoms the same shade, and then adds a touch of visual interest with a slightly lighter-colored layer on top. These keep the outfit from being boring.
- Fit. Say it with us: fit over everything. The form-fitting pants and turtleneck give this outfit a chic touch and balances out the slightly looser, airier fit of the layering piece.
A Travel Ready Wardrobe: Jen Rubio, CEO of Away
As a part of her role as CEO, Jen spends a lot of time traveling. To make packing easier, she keeps her wardrobe minimal, low maintenance, and contemporary.
But minimal doesn’t mean boring. She still incorporates trend-aware, fun pieces into her outfit rotation. Take this Clueless-inspired skirt and blazer combo. The colors, print, and fit feel in tune with the times without feeling “trendy”.
A great way to make outfits with bolder prints and colors is by matching them to a core color. Notice how she’s wearing a basic white Tee under her blazer? This keeps her ensemble clean and stylish.
Use this for your own wardrobe inspiration by:
- Seeking out matching sets. Especially if you’re on-the-go and busy, sets are a lifesaver. No more thinking about how to pair and match separates. With a set, you have a built-in outfit. Plus, you can always add pieces under or over them to make even more ensembles.
- Fit your wardrobe to your lifestyle, not the other way around. Jen admits that she likes clothes that give her time back in the morning instead of stressing her out. If you don’t have time to put together complicated outfits, then don’t! The classics never go out of style.
NYC CEO Style With Impact: Nadia Boujarwah, Founder of Dia & Co
Remember what we said about being just as powerful in a dress as you are in a suit?
Dia & Co. founder Nadia Boujarwah gets that. That’s why this past year she created a “Nadia Edit” for her clothing retail brand. This edit centered around refined sweaters, premium denim, and of course, statement dresses.
We love that because if you ask us, dresses don’t get the attention they deserve. We know many of our clients prefer the feel of pants and separates. But if you’re tired of coordinating outfits and want more comfort in your life, dresses are the way to go.
You literally just throw on one piece and BOOM. You’re done. Just add shoes and you’re ready to go.
So how do you pick the right dress for you?
- Consider your dress code. We have to start with the practical part first. A work dress should first and foremost be one you can wear at the office without a call from HR. Always confirm with your employer’s dress policy. But knee-length or longer hemlines, covered cleavage, and shoulders usually work as a safe starting point.
- Use accent colors wisely. In the photo above, you can see Boujarwah opted for a rich burgundy-red color. It’s a statement piece, but it’s also subtle. It doesn’t feel as “poppy” as Blake Lively’s pink ensemble. The rich, deep tone feels more mature. This communicates a different personal brand than Blake’s. Use colors to define who you and your brand are.
The Low-Maintenance Executive Closet: Sallie Krawcheck, CEO of Ellevest
Last but not least, we’re finishing this list of inspirational and stylish female CEOs with Sallie Krawcheck.
She’s also a great example for anyone who works in more traditional fields like finance. Her looks lean more traditional since she works at investment firms like Ellevest.
Still, Sallie uses her clothing to amplify her skills as a leader.
It’s unlikely that you’ll see her in anything oversized. Having well-fitting clothing can make such a difference in your outfit.
A great fit will help you look more put together and in shape. It may seem like a small detail, but it can make a huge difference in your look.
Finally, while style as a woman in finance may tend to be conservative, Sallie keeps her style approachable and unique by pairing her basics with more interesting items.
Take this look from Goop Health Summit. She defines her waist with a belt but keeps the look professional with a long hemline, a collar, and a button-front. Then, she adds a modern twist with a pair of tall, leather boots.
To get her NYC CEO style:
- Find updated, traditional pieces. Those old business casual and business formal go-tos have updated versions. Try a knit blazer instead of an overly starched one or a silky bias-cut midi skirt instead of an old-school pencil skirt.
- Say yes to tailoring. We know it’s an extra investment and takes time. But if you find a tailor, they’ll change your life. Most clothes don’t fit everyone off the rack. Almost everyone needs adjustments in the arms, body, and hem.
- Use accessories to make your look approachable. If you want to reach more people or show your personality, accessories are a great way to do so. Try boots instead of flats, or a lariat necklace with a conventional crewneck.
NYC CEO Style Takeaways
These seven NYC female CEOs each have a style all their own. But they all base their wardrobes on similar concepts.
They all invest in high-quality basics, core colors, and getting the perfect fit. (AKA, our NLW Style System.)
If you’re ready to take your wardrobe to the next level with our patented system, apply for our image consulting services today. Our team is ready to revolutionize your closet and change your shopping habits for good.