What if the secret to timeless style has nothing to do with following trends?

This week on The Iconic Midlife, I'm joined by legendary fashion designer Cynthia Rowley, whose career has spanned more than four decades and over 100 runway shows. But this conversation goes far beyond fashion.

We dive into why women over 40 should stop dressing for trends, how confidence evolves with age, the power of reinvention, and what it really takes to stay creatively relevant in an ever-changing world.

Cynthia also shares behind-the-scenes stories from dressing Hollywood's biggest stars, including a hilarious first meeting with Katy Perry, her philosophy on personal style, and why curiosity—not trends—is the key to looking and feeling your best.

Whether you're reinventing your wardrobe, your career, or your next chapter, this episode is a reminder that your style should reflect who you are—not what's trending.

In this episode, we discuss:

• Why there is no "right" trend to follow

• How personal style changes—and improves—in midlife

• Staying creatively relevant after more than 40 years in fashion

• Why women should stop saying, "I can't wear that."

• Building an enduring brand without chasing trends

• The difference between reinvention and constant evolution

• What working alongside her daughter, Kit Keenan, has taught her

• Behind-the-scenes stories from dressing celebrities

• The unforgettable first time she met Katy Perry

• The fashion "rules" women over 40 should completely ignore

Connect with Cynthia Rowley

Instagram: @cynthiarowley

Website: https://www.cynthiarowley.com

Follow The Iconic Midlife

Social Media: @theiconicmidlife

Social Media: @redcarpetroxy

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Website: www.theiconicmidlife.com

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Because midlife isn't the beginning of the end...

It's the beginning of your most iconic chapter yet.

101 Runway shows. Is that right?

It's been a long time, but, yeah, 101. In November, I won the CFDA award, which is, like equivalent of a lifetime achievement award. By the time I turn around, Katy Perry is stark naked.

Like, naked naked, nothing left to the imagination. I have no off switch. That's the problem. I didn't get married Till I was 30, and then my husband died when I was 34.

But then after that, I really couldn't even think about anything for years. Someone slams the door, you crawl in the window. You know, that's like, what I've been doing my whole life. I'm, like, relentless.

Billy G. King said, pressure is a privilege. Isn't that a good one?

Fashion trends come and go, but true style that lasts. Today's guest has spent more than four decades proving exactly that. Cynthia Rowley isn't just one of America's most celebrated fashion designers.

She's a creative force who has built an enduring lifestyle brand spanning fashion, home accessories, collaborations, and media, all while remaining refreshingly authentic to herself. In a world obsessed with what's new, Cynthia Rowley has built a career proving that longevity is the ultimate luxury.

In an industry that's constantly chasing the next trend, she's done something far more remarkable. She stayed relevant without losing her identity.

With more than 100 Runway shows to her name, she's dressed everyone from Hollywood stars to women simply looking to feel their best, reminding us that style isn't about following rules. It's about expressing who you are. Today, we're talking about much more than fashion.

We're exploring reinvention, confidence, creativity, entrepreneurship, personal style in midlife, and why the most interesting chapter of a woman's life may just be the one she's living in right now. Before we dive in, if you're enjoying the iconic midlife, be sure to follow or subscribe wherever you're listening.

It helps us continue bringing you inspiring conversations and with women who are redefining what's possible in midlife. Please welcome the incredibly talented Cynthia Rowley. Welcome to the iconic midlife. Cynthia, how are you today?

I'm great. How about you?

Oh, I'm so great. I'm so great. I'm just so excited to have you here. I'm glad you. Absolutely, Absolutely. And major congratulations are in order for you.

101 Runway shows. Is that. Is that right? You've had 100?

I mean, yeah. I mean, it's been a long time, but yeah. 101.

My gosh. Okay.

And we've been going through our archives, which is really cool. In November, I won the CFDA award, which is like kind of the equivalent of a lifetime achievement award.

So we had to go through all these Runway shows, and I was like, where is all this stuff? Stuff?

Is like four or five thousand pieces that we've been, you know, that we have technically probably have in archives, but I know we don't have them, but yeah, it's been. We have a lot.

That's amazing. Amazing. What a career. That too. What a career accomplishment.

Is there a collection that stands out to you or like a certain piece that is your favorite?

Definitely. No. Like, there's no way. I mean, I would say the opposite. There's some cringe worthy pieces that I'm like, oh, what was I thinking?

And, you know, some stuff from the 90s doesn't stand the test of time, while others do. And, you know, I'm like, surprised to see stuff that we did, like, you know, maybe 10 years ago. And you're seeing it kind of like in collections now.

There's a lot of stuff that's vaguely kind of humorous, like Schiaparelli style, you know, like, things like that. You'll see. Okay, follow us and you'll see we're posting. We just posted the first, but we're. We're going to be posting a lot.

That's exciting. I will say of all my, you know, Cynthia Rowley pieces, I have so many favorites, but I feel like it's timeless in a lot of ways.

Like, there are pieces of yours that I've had that I can pull back into my wardrobe, you know, here and there, like, and I love that there's like a real workability to your, to your designs and your collection.

So is that for you, something that is always in the back of your head when you're designing, or do you always go into like a new collection, just fresh and, and you know, without like anything kind of that you're thinking about before?

Thank you for that. We don't really do collections. We don't really work like that. We design, make, and ship every day because we're an omnichannel brand.

So we have to keep, you know, nobody. And people don't shop like that. Nobody goes like, oh, it's September time for my Fall collection, wardrobe shopping or whatever. You know, we don't.

We don't work like that.

We just make a lot of cool stuff all the time, and we might put it all together to show in a collection, but it's really constant creation all the time. And I think it's really just like, what.

I've worked with the same team for so long, and it's really kind of like what we're feeling now after, like, spending a lot of time with these archive pieces. We're like, you know, maybe we should see how that would have. Would evolve now.

You know, never the same, but like an evolution, you know, so when you're.

Looking back at those pieces and, you know, especially over, you know, the years of the shows, what's something that really stands out to you that you've learned about yourself? Not necessarily about the fashion aspect, but you as a woman kind of going through this whole evolution.

It's definitely like, I am who I am. You know, there's always this little. It's always sporty, but always kind of pretty and sexy.

Always a tiny wink or sense of humor, something daring or risk taking. I mean, I think these are all things that like, hap. Hopefully, hopefully happy, you know, and make other people happy.

I think they're all things that are like, part of the DNA of the brand, but they're authentic because it's part of the DNA of me and, you know, the people I've been lucky enough to work with for so long. And it's just natural. It's just natural.

So, yeah, it just comes to you, right? I just want to. So what. What is inspiring you right now in particular? Like, are there things.

Are there kind of, you know, things that are going on in life right now that you're looking towards or, like, what are the things that really kind of excite you?

Well, I do love sports, and I feel like that's been sort of infiltrating the pretty, you know, so, like, some of our pretty stuff has, like, a little bit more of a sportier kind of edge, I think. Been thinking about a little surrealism I've been thinking about. You know, it's never. It's never one thing.

Yeah, it's always just like a billion references, a billion experiences. And, you know, and because we get to design every day, you get to have an.

An idea, an inspiration, like a vision, and make it a reality on the daily, you know, so multiple times a day. So it's much easier to experiment because, you know, it's such a fast track.

So the so the influences can be coming, like, all the time from all different places.

You know, I'm so glad you brought up experimentation, because I think that's so important with style, you know, and how our personal style evolves. Right. Because, you know, what worked in our 20s, maybe it evolves, but maybe we're taking risks.

But I feel like a lot of times women in midlife sort of get stuck and, like, are afraid to take risks or, you know, they've got changing bodies, and, you know, there. There are all these different factors to contend with.

So what do you say to women in midlife that are maybe, you know, maybe want to take a little fashion risk or maybe want to, you know, update their wardrobe? Like, what. What would you say to a woman like that that might feel stuck?

I mean, I think just try one thing and, you know, branch out once and see. I mean, I don't know. That's.

It's hard for me because I feel like I want to try everything, and I don't really care if people think, you know, it's too short or it's.

Too tight or whatever.

Like, I just. I want to try it out, you know, I just want take it for a test run. And, you know, I mean, I think there's a million options. It's never. Okay.

The number one thing. This is what is hard to talk about when you talk about inspiration or timelessness or any of that. Like, there is no one trend. Like, there's no trend.

You can't. There's nothing.

There's.

Women shouldn't be thinking like, oh, I can't wear that.

They should be thinking, like, they should be curious and thinking about what can they wear and not trying to be something just because it seems popular or something. Just be curious about what. Like, everyone has, like, certain assets that they wanted focus on and whatever it is, you know, then go in that route.

But it's like there's a million different options and a million. And there's no trends, and there's no.

There's so many different ways that you can experiment and look different and look exciting and, you know, whatever you want to look sophisticated, young, old. I don't know. Whatever it is.

Absolutely.

That's the fun of being a woman, you know, is that you get to decide on the daily or multiple times a day.

Absolutely.

You know, you really made a career out of helping women be seen, you know, So I think, like, a lot of times, fashion doesn't get that and style doesn't get that credit, because it really can change the way you walk into a room, you know, it can change how you feel. It's, it's. It shapes your outward appearance, but it also, I think, shapes your inward appearance.

So do you find that style and fashion has, like, that sort of deeper rooted sense for people or is. Do you think it's mostly like, on the outside?

No, for sure. Like, so I'm going to a. I'm going to a Broadway play tonight. Like, I go to concerts, I go to, you know, I go to all kinds of stuff. Yankees games.

It's like, it's chaotic. I want to see everything.

But I'm going to a show tonight and I'm actually, I'm excited to see the show, my friends in it, but I'm really excited because I want to wear this skirt that I'm going to wear, this, like, fringe skirt, you know, so I'm. It's like getting excited about an event because you get to wear something special. You know, there's nothing worse than, like, you, you want, you.

You're going to something, but you don't have the right thing to wear. You don't have anything to wear, then you dread, you don't want to go to the thing, and then you're missing out on the fun. And that's really sad.

So, like, you know, you need to have. It's, it's an investment in your. It's like a shrink or something.

It's like an investment in your happiness to have some things that make you feel good when you put it on and, you know, things that work for different occasions, because that's what's going to give you peace of mind and confidence and, you know, have fun. I love my work. I love that I get to have access to all of that. I'm not even, like, clothes crazy. I just, like, might work. And so that is all I wear.

I don't think designers should wear other people. I mean, unless it's like an homage to someone.

Like, I'm friends with Johnson Hardig from Libertine, and I love his stuff and I would happily wear something to one of his shows to support him. But, like, it's weird going out wearing other people's clothes because they just assume it's yours.

And then you're like a fraud, you know, because it's like, I don't know, you're not giving credit to the people that created it. If you're creating it, you need to be, like, showing that you support it. You know, I'm showing that women my age can wear my stuff.

You know, I'M like, look, why are you afraid of these cargoes? Why are you afraid of. You know what I mean? So I wear it. My. My daughters wear it. We. We all wear it.

I know you were podcasting when we spoke last time with one of your daughters. So I think that's interesting to kind of, you know, fold her into one of the business, the sides of the business, you know, and kind of have this.

This show together like you guys were doing. What have you learned about that generation in particular? Because she's Gen Z, right? Is it. She's in that sort of grouping?

I think so. And then what's. Then I have a 21 year old. I don't know what that is. But anyway, we all live together. It's very fun.

We, like, watch every episode of Love island and, you know, you know, I mean, we know everything there is to know. Like, we're on social. We're all on social media doing stuff together. We're all like, there's no. It's very seamless.

The intergenerational part of our relationship is very seamless because sometimes I act, you know, I just like, right there with them at Surf Lodge sometimes. And, you know, not in a weird way, but, like, I love stuff like that. You know, I have a. I have a.

People say hanging out with me is like putting a fork in an electrical socket. So I go, just go, go, go. So evitably. They may be a part of that, you know, somewhere along the way or not. You know, we. We just.

We all three have a lot of fun, so that's so fun.

So what do you think from, like, a parenting perspective? What do you think you did right, that, you know, helped with the closeness that you guys all have together?

Like, what are some of the things you think that that worked well?

Well, I don't think there was any, like, real strategy.

I come from, like, a really loving household, you know, in a small town, and it was just, you know, my mom was always there for me, and so I feel like I'm always try to be there for my girls. And we go on big adventures and we, you know, we just laugh and like to hang out together.

We, you know, have been through a little bit of a rough time about five years ago, and I think that made us realize, like, how much we appreciate each other and how much happier we are now and how lucky we are. And so I think it's a combination of all of that.

Okay, so it kind of, like, all kind of came together. Was there ever, like, a terrible teenage period or did you kind of get lucky? And by.

Honestly, people always ask me that and I really missed that whole thing. I don't know why, but they weren't like that. I promise you, I'm not delusional.

You know, there's like a one or two incidences, but really, knock wood. I don't know how it happened, but we did not. I did not have any real drama with them. I'm not like, I'm not a drama person, really.

I mean, you know, I. Especially with them, like, I'm just so grateful. I was like, old.

I was an old mom, so I was like, oh, my God, this is a miracle, you know, so I've always been grateful that they're in my life. And so, yeah, I try to, yes, take it easy on them and they take it easy on me.

I love that. You know what? Here for it. I'm also in the geriatric mom group, and I think.

I think it's actually a really good thing because we've lived some life, right, and we've kind of gone through a lot of things by the time we become mothers. And I just think it works to our advantage.

Personally, I'm. I'm very happy. I'm very grateful. And, you know, would I have started a little earlier? Probably. I just didn't have the circumstances to do that.

So I was. I feel lucky I got to do it when I. When I did it, you know, absolutely.

Was it. Did you ever feel becoming a mom, was that ever competitive with work for you or were you able to kind of separate the two?

No, I just, I honestly, I think, like, again, it wasn't like anything that I really, like, strategized about. Like, I was just working my arse off and just like, working so hard every day. I mean, like, I still do, but, like.

And time was going by and I wasn't realizing, I guess, like, that it was sort of like now or never kind of thing. And kind of when I realized was when my husband. I didn't get married Till I was 30, and then my husband died when I was 34.

So at that would have been the time that probably I would have started or at least be thinking about. But then after that, I really couldn't even think about, like, anything for years.

And then when I finally was in a place where I, you know, the circumstances were right to maybe get pregnant, it was. It was. Yeah, it was late in the game. So thank God it worked. And then, thank God, with a little help from the medical world, it worked a second Time.

That's amazing. And you have your two.

Two girls, you know, so it's, you know, it's like you can't really, you can't. I wouldn't. I don't know. You know, I don't know. It just. It's a hard thing to plan. A lot of people plan it. It's not like.

It wasn't like I thought, oh, I have to dedicate everything I've got to my work, so therefore I can't start a family.

I always wanted a family, but I also love my work and, you know, just other circ, you know, extenuating circumstances, sort of throwing a wrench into things. So.

Yeah, absolutely, absolutely. I know. It's interesting that with time, you know, time doesn't always end up on our side.

You know, it's kind of one of those things where you're traveling down this path. And I know for me, I was just kind of like, okay, do I take that turn here or do I go straight? You know, and it's.

You can take so many different ways and different routes, but it. Ultimately, I think that where we end up, you know, is where we're supposed to be. So, you know, looking back, do you have.

Do you regret anything along the way or do you kind of feel that same way where it's, you know, you've kind of built the way and where you're supposed to be right now?

I think, I think it's better to have no regrets. I don't really. I feel. I feel lucky. Yeah, I don't, I don't think that's. I don't like to look back. I'm very optimistic and I. So I.

You can't really have regrets and be optimistic. I also think in.

As a designer and as a creator, it's sort of intrinsically optimistic because you're imagining something that you believe is going to be amazing in the future. So it's like part of the process, the part of the creative process is to be optimistic and to be forward thinking.

So I don't really think back and regret.

I love that. I love that that's part of the DNA for you, the optimism and like, you know, kind of just looking forward.

Because I think a lot of women in midlife, you know, like some of the friends that I've spoken with say that they, you know, feel like they are looking back. You know, they are thinking about like, shoulda, woulda, coulda, like, why didn't I do this, why didn't I do that? But, you know, it's.

It's a hard place, right? You're kind of in this, like, zone where it's just, you know, you. You. You've lived life, but you still got a lot of life to live, you know?

So I love that, you know, optimism has really guided you in this process. Where does that optimism come from for you? What do you, like, credit that to?

You mean, way back when, before the creative process, kind of the.

Yeah. However, it kind of came for you, like, what kind of keeps you looking forward?

I. I mean, I think it's the. The need to create. I'm just always thinking, oh, it's like, you can always have a dream if that's your job.

It's like, just you're always able to use your imagination and dream, and that's. That's pretty optimistic, I would say.

It is. It is. And it's something. Like, it feels like there's always something that you're. You're. Like a goal or something you're striving for next.

Like, it never stops. Which is, I think, really important to kind of always look forward to things like that.

I mean, that is part of the problem, that it never stops. I'm like, there's no end. There's no finish line. There's no. Just keeps going, just keep grinding. Just stay in that hamster wheel. It's really.

It is really, like a little bit. But it's exciting because things, you know, there's new challenges, new opportunities, new categories, new ideas and new partners and new everything.

And that's always exciting, right?

And on the flip side, would you even really be happy if you weren't.

Doing what you were doing?

You know, like, if retirement came or anything like that, you wouldn't be happy, probably.

There's no such thing. I have no off switch. That's the problem in both my personal life and my work life.

Yeah, I like that, though. You want that spark plug around. So what do you do when you want to shut it off? Is there, like, something you like to do to, like, kind of relax or.

Kind of. Or is there really no relaxation?

I don't relax. I actually don't relax. The only time I relax is watching dating reality shows with my girls.

And sometimes it's, like, so relaxing that I fall asleep and they're like, mommy, Mommy. Right? But that's the only thing. But I do love them. I'm so hooked on all of them. But no, I don't. There's no. I. I always have said there's no me time.

Really, I'm not that kind of Person. Like, I'm at work with. Like, I'm looking down from the mezzanine at everybody now. Like, there's a lot of people here.

There's always people at my house. It's just like, I don't. I'm not like a. Like, oh, I need some space. I'm not that person. I always like to take it up a notch.

We love that. Okay. That's fun. Like, you, you're. You're like the life of the party. Like, people want to be around you. I can see that.

Get people wound up. For sure.

Yeah, for sure. So are you spending a lot of time in New York? Like, most of the time? Like, are you going out?

Like, what are you doing, like, if you're not at the office?

Well, I walk to and from work every day, which is about. I end up clocking about five miles a day. And I try to walk everywhere and. But I work. I work until pretty late. There's a million events.

There's like, movie. I'm going to arrest my friend's restaurant opening tomorrow. My friends play Broadway, play tonight. Like a concert.

Like, there's always a. I mean, that's. Why do we live in New York if you're not, like, trying to see and experience everything?

And I have so many good friends that have, like, stuck by me when, like, things were hard. And, you know, and my squad is great. Girls are great. It's just, we have, you know, we go in the summer to Montauk. We have a store there.

And, you know, I'm also there. And so we go there and act silly, you know, and. And then there's just always something in the city. I play charades at my friend's house sometimes.

Like, it's really, you know, with the actors, and it's really fun. There's just always a lot to do.

Yeah. Oh, my gosh. Absolutely.

I love that you brought up your girlfriends, too, because I think that my girlfriends have carried me through so much, and that sense of community is so important. So what do you. What do your closest girlfriends mean to you?

Well, I have girl and guy friends. Girl, guy, gay, straight, like, all totally.

We always love our games.

I just, you know, I have a really full, you know, happy group of friends that all mixes and everybody's like, has something interesting, and it's. It's really exciting. I, I, you know, I show up for them, they show up for me. My one friend always texts me, what's up? Ride or die. We're.

We're each other's ride or die. And yeah, it's just. I'm like, we really appreciate each other.

Yeah, it's great to have sounding boards like that. You need them. You need them, you know, you really do.

So what are the things that you think they could be like, personality traits or even habits that you have that really have helped with the longevity of your career and all the success that you've had? Are there things that you've always sort of done that have kept you on this really amazing path that you've been on?

I mean, I. Again, I know I've been very lucky, but I think I work really hard. That's the thing. Like, I don't know how to not work hard. That's.

It's like, I just don't know any other way to be. So I don't. Like, I'm here on Fridays in the summer, like, it's ridiculous.

But then I go out to Montauk and I have 48 hours of insanity and then I'm back on Monday, you know, So I think my commitment to my job is like, unending. You know, I will like, do it or die trying.

And I'm always like, trying to, like, think of ways to do something in a different way and learn something new and work with different people. And, you know, I think it's like, I think this is such a gift that I have.

This thing that allows me to like, meet so many different people and have access to so many different ideas, from art to technology to science, to like, nature, to like, crazy sports. I make all the survival suits for the guy that surfed the 100 foot wave. That's like such a gift. Lindsey Von's, you know, ski helmet.

Like, it's just like cr.

That is a gift to be able to meet and, and think and learn about their world and see if I can maybe like, add a little tiny bit to what they've, what they're doing and, you know, and that's fun. So I think it's like that constantly willing, the constant willingness to try something, like, to think, like, think how can. That's really cool.

Is there any way, like, we could help? Could we be involved in that? Like, it's like that kind of thing, you know, like we.

Is there anything we could do for, like, to try to learn about that, you know?

Absolutely, absolutely. Staying open and, and trying new things, which is so important. But what do you do when things don't go your way?

Like, if there's, you know, maybe something in business that didn't work out or in your personal life, even like what?

What.

How do you deal with, like, failure?

Essentially, I always say, like, you know, someone slams the door, you crawl in the window. You know, that's, like, what I've been doing my whole life. And I'm, like, relentless.

Like, I won't take no for an answer, but sometimes you gotta take no for an answer, and then you gotta pivot, fail, pivot, pivot, pivot. You know, whatever it takes. And, you know, maybe work twice as hard.

Maybe ask someone for a favor that you really don't want to, like, have to do that. But I'll just make myself do it. I'll just do it. You know, the sweaty stuff. I'm willing to do anything. Like, I don't.

I'm not, you know, bougie about anything. Like, do anything, you know? So when you fail, you have to be willing to, like, do. Think about it in a different way. Reinvent yourself.

Do whatever it takes to maybe go in a different direction. I mean, I always think it's a blessing. I try. That's the way I. That's my survival mechanism is like, if I.

If something fails, whether I've done it, somebody rejects something, there must be a reason, and there must be something else waiting, you know, to happen. So what else could it be? And where can I focus my energy and, you know, think in a different way?

So, no, those are great points. You know, I find, too, that it is so hard for me to ask for favors from people, and I don't know where that comes from, necessarily.

I don't know if that was just something that along the way got ingrained or if that's a thing. Like, maybe at this time of life, it's just harder to ask. I don't know. But I actually was thinking about that the other day.

I'm like, why is it so hard to ask for a favor? So I think it's really interesting that you're bringing that up. I mean, is there a reason for you why that might be more difficult?

Or, like, if you're just, like, that person that's, like, constantly doing, doing, doing, then, you know, it's hard to maybe ask for a favor and then put them on the spot, you know? Yeah.

It's also kind of vulnerable, too, to put yourself out there like that. Right. Yeah. Which vulnerability is not, my friend. I'm, like, working on it, but it's hard, you know, are deep.

If something fails, like, just bail. Like, that's what I mean in my personal life. Just my thing is, like, if it's not working and you Try and it's still not working. Fail.

Like, do not suffer. Do not suffer emotional abuse. Do not suffer through something for some made up reason that you think you have to stay.

Stick around, get out, you're gonna be happier. It takes. It might take a while, but in the end, I think more your self is for your self esteem and everything else.

I think that that can be applied too to both, you know, platonic friends and romantic partners, you know? Right, totally. Because I don't know, but. But the older I get, I feel like my friends even like thin out a bit.

Like I'm kind of seeing, you know, who's really the. The people who are the people that I really spend the time with, you know? Yeah.

I mean, sometimes it just happens organically, but rip the band aid off.

We would be remiss if we did not talk about Hollywood because you have definitely dressed some of the biggest, you know, actors, models. Like, I think the last time we spoke, we had a funny little. You were telling me a story about a certain actress.

I could tell the story because it is funny. Pretty funny, I guess. My friend is a painter named Will Cotton, and he paints.

We've collaborated on things and he does these paintings that, you know, shows at galleries around the world of these women wearing like confections, like a cake on their head. Or like he paints like very magical, imaginative, fantasy kind of paintings, but portraits. So Katy Perry's album was coming out and she has so many.

I can't remember what number it was. But he was like, I'm doing. I'm gonna paint her for the COVID And I was thinking about a cupcake dress.

Like a silver cupcake, cupcake cup made into a dress. So I was like, of course. Got it.

So I made the dress and I got to his studio for the portrait sitting where he was going to take her photo and then eventually paint the portrait. And I was like, okay, here it is, here it is. And I was like getting it out of the bag and like from behind me.

And by the time I turn around, Katy Perry is stark naked. Like, naked naked. Oh.

Nothing left to the imagination.

But let me tell you, she looked beautiful. Like perfect. And I was just like, here you go. Well, yeah, let me just help you get this on, you know. But it was like she was not shot. She.

That was the first time I met her. And she was just like, you know, I don't know, I thought that was kind of funny.

Yeah, I mean, gosh, she probably. That's probably like all in a day's work for Her. Right. Getting naked and just, like, having people dress her and, like, gorgeous.

She looked like perfection.

The next chapter. What's coming up? Like, what. What are you most excited for?

I mean, every day I feel like I'm excited to be here. It's really, like, if there's endless. Really, there's endless projects. I was thinking, like, right now, like, do I start naming stuff off. Not really.

I think it's just. Stay tuned. Follow us on Social. And, you know, it's really. There's a lot of collabs coming out over the next a few months. And as well as.

I don't know, there's, like, so much stuff. We have our surf camp coming up in two weeks. We have. There's, like, a. So much stuff. It's a lot. Just f. Just follow. There's no time off.

You know, there's no. Let me just get my head above water. Let me just take a break for a couple months. Nope. You know, this is not. That's not part of it.

Absolutely. As I like to say, we fly the plane as we're building it. You know, there's no Right. We don't step off. We just. We just keep going forward.

We just keep going forward.

I tell you one. This is actually a really funny story. I just thought of when I was. They asked me, would. Would I ever be on Jeopardy? Like, Celebrity Jeopardy, Right?

So I was like, yeah, definitely, because I've always wanted to be on a game show, but I kind of had something more like Hollywood Squares in mind or something easy. Then I was like, how do I study for all the knowledge in the world? I'm like, okay, this is terrifying.

I'm playing against two geniuses, and it's for charity, so it doesn't really matter. But anyway, so we're. I'm playing, and it's really hard because you got a buzz. And so I see the board, and I'm like, okay, here we go. This is a setup.

They must have done this just for me. The header is from the Runway. So I'm like, all right, take. Like, I'll take from the Runway for a million dollars. Whatever.

The highest one was a thousand or something. And the. And Alex Trebek is like, okay, Cynthia, this Boeing 747 was first launched in what year? And I was like, what? Because it's an airplane.

Oh, Runway.

Runway. I kind of feel like we need to see you more on tv, though.

Tell Bravo would you do it? Of course.

Wait, what about Roni? Real Housewives of New York. That's what would You.

That's what people say. I would do it. I think it'd be fun.

You. You would do it.

You want to.

Okay, we need to let Andy Cohen know. Does he know this?

No.

Oh, my God. Andy Cohen. We're calling you right after the show.

Like, that would be him on his Instagram.

I will. Oh, my God. Hello. You would save the show? We got to save the show.

Well, I would do that. You know what? I wouldn't do the thing that everybody has asked because Kit was on the Bachelor. Everybody says, why aren't you on Golden Bachelor?

And you know why? Because I don't want the guy. That's why.

Wait, do you skew younger when you date?

I don't know if I can reveal that information. You could probably best.

My. My bet is yes. We need somebody with, like, a lot of good energy. 100%.

Your kids are like, your teenage boyfriend's waiting for you outside. I'm like, okay, thanks, guys.

He's like, wait, who am I here to pick up?

He's like, daughter.

Daughter, mom.

They just joke around. Anyway.

What? Why not? You know why not? I mean, I say I'm here for it, so hallelujah. Do it, do it, do it.

Did you happen to catch Jenna Lyons on Roni when she was on it?

She's a different person. She's a different person than me. I love her. She's great. So smart, gorgeous.

Very, like, you know, I'm a little more of a loose cannon, I would say, which is why. Might be a bad idea, but whatever.

At this point, or the best idea, we're gonna. I'm gonna be DMing Andy Cohen on that again. So, Cynthia, what advice would you give your 25 year old self?

I mean, I didn't really know anything when I was 25. I was really naive and really, like, clueless about everything in the fashion business. And guess what?

It was a time when you couldn't get information. Like, we had freaking Rolodexes, you know what I mean? And telephones. Like.

Like, there was no, if you're lost, you're lost, you know, like, there was no. You know, there wasn't any way to learn. So it just.

Everything was harder, but so, you know, you had to work, work harder because everything was harder. And now I think it's so much easier and more fun and just different, you know, it's not easier, really, but it's different.

Was there like kind of a. A lesson or a turning point in midlife, specifically?

Spend as much time with your kids as you can.

Yeah. That's a big one. That's a big one. I mean, that. That goes so quickly.

Say yes to every opportunity that you can because you know what no is going to look like. But when you say yes, you can always say no later. But no is a real dead end.

And I also think it's a little bit of an attitude thing, so trying to appreciate all the opportunities you're given. Oh, this is a good quote. Billie Jean King said, pressure is a privilege. Isn't that a good one?

That's a really good one. That's a really.

If I have the chance to do something super fun, go, why the hell.

Not, like, do it, you know? Thank you so much, Cynthia. It's been amazing. I loved having you on and it was so fun. And everyone can find you at Cynthia Rowley on social media.

Is there anywhere else you would like people to go to keep up with you?

I mean, just check our website, check our socials, and visit any stores you might living near. And yeah, DM me. If. For any. If you have any thing to say. DM me.

Yes, absolutely. Thank you so much, Cynthia.

Great pleasure, Great care.

What I loved most about this conversation is that Cynthia reminded us something we all need to hear. Reinvention doesn't have to be loud sometimes it's simply having the confidence to keep evolving while staying true to yourself.

Whether we're talking about fashion, creativity, confidence, or building a life that's authentically yours, her message was clear. There are no expiration dates on curiosity, ambition, or personal style.

If this conversation inspired you, I'd love for you to share it with friend who's embracing her own next chapter. And if you haven't already, be sure to subscribe to the Iconic Midlife.

Wherever you listen to your podcast, leave a review and follow us on social media, heconicmidlife and edcarpetroxy for more conversations that celebrate the power, positive responsibility, and reinvention that come with midlife. Until next time, remember, your most iconic chapter may still be ahead of you.