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Ageless Style a Stylish, Elegant Couple, You Will Love

I am beyond thrilled to be interviewing the oh-so-chic Andy Poupart and Michele Free. Andy was one of my first interviews when we started this series back in 2017. I have been dying to interview Andy and Michele as a couple. You know them as the Instagram Sensation Mr. & Mrs. Style After 50. Let’s take a look at Ageless Style a Stylish, Elegant Couple, You Will Love.

This feature is a collaboration between the uber-stylish Contessa (from the Vintage Contessa) and myself. We started this series hoping to showcase women and men over 50 with great style. Michele and Andy ooze style. Let’s get into it. FYI you can read my original interview with Andy on Ageless Style here.

Ageless Style a Stylish Elegant Couple You Will Love

Ageless Style A Stylish Elegant Couple You Will Love

I have watched Andy and Michele evolve on IG. Andy started out on his own and eventually wove his darling wife Michele (perhaps reluctantly?) into the fray. What happened in my opinion was magic. Michele is charming self-effacing, and real. She added a new dimension to the mix.

Tell us a little bit about your history and how the two of you met

We met at a company we both worked at in the early 2000s. At that time we were both married to other people, but I think it’s fair to say that neither of us was entirely happy. We were colleagues first, then friends, and, eventually, we became romantically involved. After a long road, we were married in 2013.

Strangely enough, we both worked at Apple in the late ‘80s to early 90s but we never met. From our time at Apple, we have a number of friends in common, but we did not meet until years later, as Andy described.

Andy Poupart and Michele Free Style After 50-Ageless Style A Stylish Elegant Couple You Will Love

Tell us a little bit about your professional lives outside of Instagram


I work for a large consumer electronics company based in Cupertino, California. I manage a team of software engineers.


I am a corporate trade show and event producer, most recently working in the cyber security industry.

How did you two become an Instagram Sensation?


I don’t know that I would call us a sensation, although that is kind of you. I started posting seriously on Instagram some years ago at the urging of one of my daughters. Our follower base began to grow much more than we ever imagined it could and we get a lot of very positive and encouraging feedback. In addition, we have met so many wonderful people around the world, through Instagram, many of whom are now friends in real life. Plus many opportunities have become available to us that would certainly not have happened if it were not for Instagram.


Andy is the social media half of our team. But I think our strongest content comes when we play off each other in videos. We’re just being ourselves and having fun. I wouldn’t participate if it wasn’t fun to create content together.


I love how Michele’s humor has recently played a stronger role in your Instagram reels and stories.  Tell us how that came about.


I think Michèle is one of the most naturally funny people I’ve ever met and I love to showcase that side of her in our Instagram posts (and more recently, reels). Back at the start of the pandemic, we videoed some answers to an Instagram “ask me anything” story, which turned into “Life with Michele and Andy” Instagram TV segments. These segments were very well received and I think we’ve kept that going.


We started doing “Formal Friday”, also, fairly early in the pandemic and I think since we started producing video segments the way we interact with one another naturally includes a great deal of humor and affection. I hope that’s what people see, at least.

How would you describe your personal styles?


 I think the way we dress tells a story about ourselves, or at least a story about how we want the world to perceive us on any given day. I try to look well-dressed as a way of expressing courtesy. I think my style, such as it is, is mostly an English style with some idiosyncratic elements thrown in. I do not have to adhere to a dress code at work, so I can afford to be more experimental, perhaps, in the clothes I wear. I love color, and I love cream things. I have more cream suits, jackets, and trousers than any one person could possibly need.


I usually describe my style as professional, sleek, fitted, and not fussy. I usually wear a skirt, top, blazer (why is it always so cold in offices?) and heels.  I find that the fit and style of White House Black Market usually works well for me, especially pencil skirts.  Ann Taylor and Banana Republic are also part of the wardrobe. I like to mix and match different combinations.  Depending on the season and my mood, I put together outfits that are monochrome or a combination of solid and patterns with a pop of color.


Who and what currently inspires you and why?


I tend to copy or adapt looks that I like. I have a number of friends whose style I admire greatly and from whom I draw inspiration. My favorite movie of all time is Casablanca. I had my tailor make me a dinner jacket as close as possible in style to the one Humphrey Bogart’s character wears in that movie. Also, The Thin Man is another movIe that inspires me, both sartorially and from a lifestyle perspective.


Aspirationally, Princess Diana – I’ve always thought she was chic and fashionable!  She always seemed to look comfortable in her wardrobe whether it was formal or casual. I think we continually evolve and change. Twenty years ago I never would have worn the kinds of dresses that Camille Flawless makes, but now I love them. Similarly, I no longer dress the way I did in my twenties. I think there is an age-appropriate, yet age-defying element to my style.

Andy and Michelle are featured here in the Androniki interview I love this picture of the two of them.

Andy Poupart & Michele Free Pitti interview

Do you have a signature piece that defines your style? 


A double-breasted dinner jacket. Whether my ivory one (the one I mentioned above) or my black one, I feel good when I wear one.


A pencil skirt and Jimmy Choos.

Has anyone in particular influenced your style?


Apart from real-life people, Fred Astaire, Cary Grant, and Humphrey Bogart are style icons.


Apart from what I wrote about Princess Diana, I wouldn’t say that I’m influenced too much by any one person.


Do you have a particular diet or exercise regime that you follow?


I keep my carb intake as low as I can and we try to run at least 4 times a week. We run a loop in our neighborhood that is about 3 miles. 


I’m not as rigorous about minimizing carbs as Andy is, but we pretty much share the same diet. Regular exercise is very important to us both.

What advice do you have for other men and women over 50?


Keep in shape. I think staying fit and in reasonable shape is the key to looking and feeling good about yourself. Having a wardrobe of bespoke clothing is a very good incentive to stay in shape.


I also think that it is important not to listen too closely to what other people think. Age is just a number and while it is important to not pretend that you are 20 again, you should be and dress in a way that is true to who you are.

Editors Note: I love this photo of Andy and Michele when they were featured in The Rake here

andy & Michelle Poupart

What advice do you have for other men and women over 50?


Keep in shape. I think staying fit and in reasonable shape is the key to looking and feeling good about yourself. Having a wardrobe of bespoke clothing is a very good incentive to stay in shape.


I also think that it is important not to listen too closely to what other people think. Age is just a number and while it is important to not pretend that you are 20 again, you should be and dress in a way that is true to who you are.

Ageless Style a Stylish Elegant Couple You Will Love

Thank you so much, Andy and Michele. I just want to mention that we all “meet” people via Instagram. I have wanted to feature Andy and Michele together for a long time but just got busy with life, the move etc. The person that I was going to feature this month ended up in the hospital so I was in a bit of a pinch. I contacted Andy and Michele literally days ago. They have busy professional lives. Guess what they were traveling and they said sure. My point is in this business we are all professionals or try to be. When someone you have a connection with says yes it means a lot. They are not only professional, but they are also nice people. Give Andy & Michele a follow on IG and tell your friends. If you love style, and great cocktails, you will love them. They are just plain fun. I hope to see them soar even higher on Instagram.

I hope you enjoyed Ageless Style a Stylish, Elegant Couple, You Will Love. You can read all of my previous Ageless Style Interviews here. If you or someone you love would like to be featured on Ageless Style email me.

Now let’s pop over and visit the Contessa and see who she is interviewing this month. She always finds someone fascinating. Click on the link below to read more.


Reader Interactions


  1. Mrs. A.J. Millington says

    ~ What an enjoyable article! Reminds me of my husband and me. We live in the Mountain State and while we have our own unique styles, I am a [mountain] cowgirl to my core. I’m a huge fan of Double D Ranch, Brit West, Vintage Collection and Old Gringo boots and I wear cowgirl boots year round. Cowgirl hats and lots of turquoise for this former New Yorker. My husband’s style in suits is the William Powell look with cuffs in his pants. We’re both in our 60s, dress the way we want and don’t care what anyone else thinks. I applaud this couple in their unique style and not caring what anyone else thinks. ~

  2. Robin says

    What a darling couple, Cindy!
    They have so much fun together.
    I imagine like you and Steve share together!!
    Thanks for sharing with me.

  3. Nena ivon says

    Fabulous post, what a super stylist interesting couple who obviously have fun with each other.
    A true joy to get to know. Thank you for sharing them with us.
    All best, Nena

  4. Elizabeth@pinecinesandacorns says

    Cindy, another wonderful interview. I already follow Andy and Michelle because of your interview with Andy years ago. I love their classic style! You are so right about the people we “meet” on social media, there are so many wonderful people who become friends even though we have never met them. Yourself included. Happy Weekend!

    • Cindy Hattersley says

      Hi Elizabeth

      I feel exactly the same way about you. Hopefully we will have a chance to meet in person one day!

  5. Heidi says

    Hi Cindy,
    I remember when you posted about Andy years ago, and I thought it was so refreshing to see a man who dressed well. I still feel that way, and as a couple they are adorable and well dressed and fun! I’m following them on Instagram now!
    Enjoy the long weekend,
    Xo Heidi

    • Cindy Hattersley says

      Hi Heidi

      I completely agree about Andy. I think the two of them are just darling!

  6. Gray says

    Just had time to read this. They are so much fun and inspirational, as far as the dressing up goes! I admit that I’ve gotten really slack since Covid. I am weighing way more leggings and sweatshirts than I should be. This was great inspiration to wear all the beautiful clothes that are hanging in my closet…

    • Cindy Hattersley says

      Hi Gray

      Haven’t we all gotten lax? I wear yoga clothes most days!!

  7. 1010ParkPlace says

    They’re so fun, Cindy! What fun! Thanks for featuring them. xoxox, Brenda

    • Cindy Hattersley says

      Hi Brenda

      Aren’t they a kick? I am so glad you enjoyed them. How is the book coming?

  8. Karen B. says

    I always enjoy “meeting” people through your Ageless Style series. It’s great to see people enjoying life and remaining true to who they are. I love Michele’s style and the couple appear to have fun. Thank you.
    Karen B.

    • Cindy Hattersley says

      Hi Karen

      I have a couple really special ones coming up that I think you will enjoy!!

  9. Stephanie Donavan says

    Love love love their trifecta of style, health and humor!
    Loved this pic, Cindy…super cool couple.
    aka tendrheart4

  10. Dee BlAck says

    Bogart Yes! I can’t stop looking at the little black dress with drop back. Wow! This is one stylish and accomplished couple.
    Pure Glamour.

  11. Juliet says

    Cindy … this was so much fun! I adore Andy and Michele … what a great couple. I came across Andy years ago and lost track … and I love finding him again teamed up with his amazing wife. I just followed them on Instagram and will probably lose the rest of the day scrolling through their delightful content. I love this series and today’s guests! xo

  12. Trish says

    They are so elegant! Thank u for treating us to their lives. Andy’s style of bespoke jackets and tailoring is certainly aspirational. Gorgeous couple…

    Cindy, love hearing the behind the scenes juggling of “making it work.” The realness is appreciated by me.

    • Cindy Hattersley says

      Hi Trish

      You are absolutely right! I need to have you do a few things for the new casa!! Summer pillows for one!!

  13. Ms. Mary says

    A very elegant couple- super interesting interview! I’m off to follow them on IG. Thanks for the efforts you put into these posts.<3

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