Bobbie Casalino Lewis: The Ageless Style Icon Redefining Confidence

Bobbie Casalino Lewis is a renowned visual style expert and motivator, known for helping confident leaders show up powerfully in the world. With her signature blend of chic elegance and bold authenticity, Bobbie empowers clients to align their attire with their brand and message—because in her world, how you show up speaks louder than words.

Her transformational work has dressed Tedx Image maker from Manhattan Beach, California, to stages across the globe—ensuring each one radiates presence, purpose, and professionalism. As a trusted style partner for Global Woman and beyond, Bobbie’s influence goes far deeper than fashion: she reshapes confidence, reignites self-worth, and turns everyday individuals into magnetic leaders.

An author, on-camera expert, and sought-after podcast guest, Bobbie bridges generations with her timeless perspective, proving that age is just a number—but confidence is forever.

Your journey from wearing hand-me-downs to becoming a VP in the International Communications Industry is inspiring. How did your personal experiences with style shape your approach to empowering others to show up powerfully?

There were good and not-so-good experiences that shaped me. First of all, personal style extends beyond just what you wear; it is the way you carry yourself, speak, stand, and treat others. These all exemplify your style – then you wrap yourself in the complimentary garments, and you have a win-win.  My low point was being filmed for a Sales training video, and when I saw it, it could not be unseen. It was awful and detracted from my presentation in every way possible, including draining my energy. The next day, after throwing those garments away, I dressed upbeat in great colors and perky style, and that presentation was outstanding. A high was presenting to the Board of Directors at the company I was heading a department at on Wall Street – I travelled to corporate offices in Stamford, CT and was dressed in well-fitting pieces that conveyed confidence, competence and grace. Presentation went so well, I got double what I had gone for.

You’ve helped clients renew relationships and expand confidence. Can you share a memorable story of a client who experienced a profound transformation through your style of expression guidance? 

Yes, happily, there are so many, but the very first warmed my heart, so I will share that one. My client wore all black, primarily track-type outfits, every day, claiming all kinds of reasons. She was a gal in her 80s and had been marriedfor  around 60 years. Her husband never remarked on how she looked or gave her compliments. I convinced her to try a colorful outfit that showed off her great shape. Well, she called me in tears because her husband not only noticed her but took her out to show her off. Love it when that happens.

In your book, So That’s What 70 Looks Like: The Essence of Aging Gracefully, you delve into the topic of aging. What are the key principles you believe help people age with grace and confidence, especially when it comes to personal style?

Well,l first of all, aging is inevitable, while Growing Old is optional! So, with that in mind, chasing youth and hiding from aging are both to be avoided. Having a healthy attitude about yourself, being confident, willing to try new things, being curious and being approachable are all key aspects and translate into personal style in multiple ways. And for me, the biggest of all is KINDNESS, it wears well in any color at any age.

As a Boomer bridging the gap with Millennials, what are some of the most significant differences you’ve observed in how different generations approach personal style and confidence?

This is a tough one, as time has influenced these two generations very differently. The pace of change for Millennials is so much quicker, aided by social media, making self-determination around style very difficult. Most are taking the most unobtrusive path possible, up to and including hiding in plain sight. Pale washed out colors, boxy shapes and in my opinion, dull choices. They are eager for role models other than the Kardashians and take advice readily. While the Boomers have this, I cannot wear that attitude, being deeply entrenched in what they have been conditioned to as age-appropriate, also dulling themselves down. Both generations can be swayed gently into a more unique personal style, incorporating some existing pieces augmented by different pairings and a few injections of well-styled new items.

You’ve had an extensive career as a columnist and TEDx Image maker. What are some of the most common misconceptions people have about personal style, and how do you help them overcome these?

I have nothing to wear – I cannot wear that – I am too fat – I am too this and that. The biggest is the waiting game – when I lose the weight – when I make some more money – when I when I when I. I approach them gently and explain they are perfectly wonderful just the way they are, and dress them to help them believe it. I am a master at using what is in their closet and bringing it to life in a new and inspiring way, uncommonly pairing it, thereby drawing them out of their rut. Creating a style around their Essence rather than their waistline. Asking them to be Kind to themselves and trust me – if my suggestions don’t work and they don’t get any compliments, we can always go back, which we never do.

Being an image maker and on-camera expert, what are the top three tips you would give to someone preparing for an important public speaking engagement or media appearance?

Several things: Know who your audience is – Know what your message is and how you want it to land – Know your stage (colors, size, lighting, height) 

Your clients are often confident leaders. How do you help them break through barriers and become even more impactful in their roles through their style? By anchoring in who they are, reviewing the successes and what impact they want to have and on whom.
Once again, we dress them to those key elements using colors that resonate, structure and texture to reinforce their message and appeal to their audience.

As someone who thrives in both professional and personal spheres, how do you balance being “fun, chic, and smart” in your own life, and how do you encourage others to find that same balance?

I am the same person no matter what I do – I have a triangle of core values that hold me snug in all circumstances. That triangle is Bravery – Integrity – Kindness; they have no expiration date. The clothes are easy, depending on the activity, because they have all been selected out of love. Only buy what you love, and it will always work.

What role does self-awareness play in creating a unique, personal style, and how do you guide clients to discover their authentic selves through their wardrobe choices? 

Self-awareness is the entry ticket that never expires. Since we are all unique, our style will naturally mimic that. Using what they have already purchased is very affirming and creates my favourite phrase – “ I never would have put that together, but I love it” .It is the truth, it was hanging there in front of their eye, and now they see it in a new light and thereby themselves as well.

In your work with individuals across various age groups, how do you tailor your approach to helping each person feel confident and empowered in expressing their unique style?

Pretty much as you have asked, the question. I build a unique composite of their attributes, ambitions, and detractors and then build a customized response to What am I going to wear? Developing what will suit their lifestyle, complement their message or brand and enable them to be comfortable in being who they are in all circumstances.  

Also, I always recommend finding a great Tailor!!!