Michelle Tomaszewski Says The Game Gets Better With Age

Wardrobe stylist Michelle Tomaszewski is in her ‘50s – and is just getting started. She discusses styling, reinvention, and the way she never grows old: by never tiring of growing.
Michelle Tomaszewski Says The Game Gets Better With Age

“Turning 30 was really scary. Turning 40 was kind of scary. When I turned 50, I felt liberated. I can still kick it. I can still dance. This age is where I want to be. I want to be an inspiration for middle-aged women, reminding us that we can still compete in the game of life. There’s no limit. We still got it. I’m better at my game than I ever was – and I still have so much more I want to do.” 

For Michelle Tomaszewski, the game is wardrobe – from costume design to celebrity fashion styling. After a decade of traveling the world as a model, Michelle started working as a stylist, realizing that the role fit her better and made her feel far stronger. Twenty years and countless projects later, Michelle still arrives on every set determined to make it the best job ever, the best day ever, and her next opportunity to get better than she was yesterday. 

“When I grew up, women were supposed to get married and have children. I decided not to do any of that and focus instead on being the best person that I could be, without those pressures on my life. I wanted to be able to help the lives that are already on planet Earth. And to be happy about who I am.” 

“I’ve been a freelancer since the age of sixteen. First as a model, now as a stylist. In the seventh grade, my Home Ec teacher brought a model into our classroom, and that opened my eyes to the career possibility. I realized that my beauty was something that might let me see the world – and it was. I was fortunate enough to travel the world for a decade.”

“My mom had me and my sisters at a really young age. She didn't get to do all that she wanted to do in her time (her dream was to be an interior designer). So, she raised the three of us to be strong women; made sure we all knew our self-worth and were going for what was good for us.” 

“I went after these things through modeling – but the industry was different in the ‘80s and ‘90s. You were always judged by your body and it wore on me after a while. The men at the agencies and a lot of the male fashion photographers really treated models the wrong way. It preyed on my psyche. I slowly started to hate it. Then, a good friend of mine who was a stylist said, ‘You should start assisting.’” 

“It was then that I discovered what my real passion was: wardrobe styling. I started doing wardrobe in early 2000. I guess time flies when you're having fun. I've been very fortunate to meet a lot of great people along the way to teach me the game of wardrobe.” 

“When my stylist friend gave me the opportunity, I immediately thought: this is it. This is my life. I feel so much stronger. So empowered. I had a goal, I got myself together, and I went after what I wanted – instead of waiting for others to judge my body.” 

“Wardrobe is in my blood. I just had to go through a few other paths to figure out what my passion was. When I was 30, I thought, ‘What am I going to do?! I'm never going to stick anywhere. How am I going to achieve anything?’ Then, I found that styling was what I love. I met really good people that gave me great opportunities and worked really hard to get to where I am now.” 

“My experiences as a model helped me know how to deal with a set, clients, a photographer, how all that works. And because I had been treated like an object, I knew how to nurture my clients – whether they were celebrities or models – and make them feel more comfortable and confident on set." 

“I was largely self-taught and still feel that I’m learning every day. I feel like women so often reach mid-century and think life is over, but I feel like my life is just beginning. I’m intent on reminding other women my age that they can be doing the same.” 

The impressive arc of Michelle’s career has led her to experience a range of expectations around women, beauty, age and power. As she grew into her powerful stance on age, the fashion industry was shifting alongside her. 

“Today’s world is more transparent. Womanhood looks different. So does modeling. You don’t have to be a young woman to be a model. It’s an open market. There has been a movement of sorts within the last year that says: you don’t have to be this one way. Alongside the fashion industry, politics and women’s rights are growing stronger. We can do this. All of us. The world is changing.” 

“I have a 16-year-old niece that I try to empower each time I talk to her. I tell her that anything she is feeling right now – about friends, boyfriends, social pressures – don’t worry about it, because twenty years from now, that will all just be a notch in your belt. You need to own your self worth. Don't waste negative energy on negative people. Keep going.” 

“My approach to never growing old is to always love growing. My line of work conditions me for new beginnings. Every time I do a job I always learn something new. When someone asks me, ‘What’s been your best job?’ Well, each job is my best job. I look forward to each day I get to do what I love to do.” 

Styling jobs are not Michelle’s only marker of reinvention. Shaving her once long hair marked the transition from modeling to styling – and the continued upkeep is a reminder that reinvention is always available to us, wherever we are in life (or quarantine).

“I used to have a lot of hair. I used to be all about my hair, since I was five years old. When I stopped modeling, I shaved it all off. It was the next chapter of my life. I just let it go. And by doing that, I freed myself and stepped into my new life. Now, I shave my hair every two weeks – and that’s always when I feel my best.” 

“Even though this is a really sad time in the world, I am looking forward to the modes of renewal that will come with it. I’m looking forward to living life after this reset button that is happening right now. Every daily regimen that helps you find your inner peace during quarantine is a reset button for the next chapter.” 

“We have to use this time to find our inner peace, what makes us really happy, what makes us want to be a better person. That’s what the world needs right now: to recharge, rebirth, and be better coming out of this.”

“A major part of our rebirth during this time in quarantine is to fully recognize that racism in this country is a public health crisis. We as a society cannot continue to grow into a better nation until we fully realize that Black Lives Matter, demand changes and rewrite the real history of how this country was built.

“If it wasn’t for Black Culture I wouldn’t be the person I am today. What my Black friends & family have taught me since I was a kid growing up in Ohio was how to love, how to dance, the best music, and not to mention style and grace. But most of all, they taught me how to fight for what you believe in. And how to demand equal rights for all.”  

“I feel the Fashion and Film/Commercial industries need to diversify on all levels. A great site to follow is Black In Fashion Council, for updates on actions we can all take to advance Black artists in fashion and beauty. We all need to do better. We all need to rise up for the long haul. We White people need to be open to learning and listening at rapid speed. This is a reset button. Things have to change.” 

Interview and Article by Molly Virostek. Photographed by Ira Chernova.

Tags: bodytalk , Womanhood

More Bodytalk

Kelly Mittendorf on Finding Authenticity

We’re back with Kelly Mittendorf, two years after our initial conversation. From stepping into her own truths and coming ‘out’ during a pandemic, she shares how far she has come.

Read more

Support Stories

This Mother’s Day, we’re celebrating support in all its forms. Read Team CUUP's Support Stories here.

Read more

Sustainable Support

From sustainable materials to a bra-recycling initiative, we wanted to take a moment to share our progress towards curbing our environmental impact.

Read more

Care for Your CUUP

We put together a step-by-step guide for how to keep your CUUP bras looking and feeling their best.

Read more


Comments will need to be approved before being published

Excellent article about an amazing woman.
Thanks to CUUP for celebrating women of all ages and for selling items that are comfortable, beautifully made & that make every woman feel her best no matter her age.


Jul 2020

What a great article Tracy your still shining inside and out representing 50 with pure class and perfection !


Jul 2020

Loved what Michelle Thomasewski has to say. For me, same! Kicking it in the 50’s and letting go of the ego. Death to ego. It’s let me become the me I was meant to be finally. Let all those little demon voices go who tell you what you are trying it dumb or small or not good enough. Because every new thing starts that way, of course! beauty is vulnerability and growth is tender. So toss that voice to the curb and just keep going.


Jul 2020

Well I’m inspired! Thank you Michelle and cup! XOx


Jul 2020

Truly a wonderful beautifully written piece of work. It is a real insite into who Michelle is and we are very proud of what she has accomplished. No one like her and so deserving of praise and a big “Thank You” for who you are. Blessings.

Deanna Tomaszewski

Jul 2020

Join the Conversation