What happens when a legendary fashion designer weighs in on today's biggest style debates?

In this bonus game episode of The Iconic Midlife, fashion icon Cynthia Rowley plays Runway or Run Away?—sharing her unfiltered takes on fashion trends, style "rules," and the looks she'd happily embrace...or leave behind.

From sequins before noon to visible bra straps, flats vs. heels, and the idea of "dressing your age," Cynthia proves that confidence and curiosity will always be more fashionable than following someone else's rules.

Whether you're a lifelong fashion lover or simply looking for permission to wear what makes you feel amazing, this fun, fast-paced episode is full of laughs, surprises, and timeless style wisdom.

🎙️ Enjoyed this bonus episode? Be sure to listen to my full conversation with Cynthia Rowley for even more insights on creativity, reinvention, confidence, and building an iconic life on your own terms.

Follow @theiconicmidlife (show) and @redcarpetroxy (host) on social media for more inspiring conversations and bonus content with extraordinary women redefining what's possible in midlife.

Dressing for your age, run away. Visible bra straps.

Even, like, a bikini top with something that you're obviously not coming from the pool or the beach, but you just put a bikini. Yeah. Love. Hot pink.

What about as a cheat code? Like, if your feet are hurting and you've, like, a long.

No, no, no, no, no. People carry the flats in their tote so that they can.

A real New Yorker, too, would wear the heels and, like, suffer through. That's like, kind of a rite of.

Passage when you're a New Yorker, like, somewhere in sneakers. Hell, no. Somebody told me about a woman who was 90 who wanted to wear heels so that she could go out for, like, dinner in heels.

I was like, oh, my God. I'm kind of obsessed with her. So let's play our fun game. It is called Runway or runaway.

So I will read these cues off to you, and you tell me what you think.

Okay. Look.

Okay. Low rise jeans. Runway or runaway?

Runway. Love.

Okay. Love. Okay.

I love them.

Okay. So more. We'll be seeing more of that, like, you think?

Okay.

Okay.

Dang it.

I need to do my dance.

Okay.

Dressing for your age, run away. Thank you very much.

I definitely am age dysmorphia. Good.

We need that. We can't think in those terms of dressing our age. I love that quiet luxury.

I. I feel like it's not my thing, but I do think it's very beautiful. So I would say Runway, just not for me, you know, maybe a little bit for me, but not run away. Definitely not run away.

Okay. Definitely not run away. Matching sets.

Love, love, love.

Okay, perfect. What about crocs?

That is a tough one, because actually, this is more of a philosophy. I think if something is polarizing, it's interesting and exciting. So I think they've. They've evolved. They've been around a long time.

Kind of like me, like, maybe in, and then maybe a little bit less in, and then maybe like. You know what I mean? And now. I don't know. I think. I think they're cool. I think they're cool.

Yeah, They're. Now would you wear them?

I have a pair. Yeah. Okay. Okay. I don't know. I mean, I also. They're functional. You know, any fashion item that has a, you know, is. Has functionality. I think is.

Is also interesting.

Absolutely. Absolutely. Okay. Sequins before noon.

Hell, yeah. What? That's not even a question,.

Right? Sequins all day long. Visible bra straps.

Love. Or even, like, a bikini top with something that you're obviously not coming from the pool or the Beach. But you just put a bikini, like, to show. Yeah.

Love hot pink bra, like color. Colorful bra. Even like black, white. I don't know. I think it's cool. It just is. Like, it depends how you do it. Like, you don't want an ugly bra.

That would be the caveat. A pretty bra.

Yes, yes, definitely. Into it. Okay. Oh, white after Labor Day.

I mean, that's just ridiculous. Nobody cares about that. That's like wearing white gloves and a hat to church or something.

To me, I don't know that that whole idea is like ridiculous.

Totally. Wearing sneakers with an evening dress.

I don't think so.

Okay, so that's a no go. That's a runaway.

Yeah, I don't think so. Sneakers for every everything else. Of course.

Okay, what about as a cheat code? Like if your feet are hurting and you've like a long cheat code. Okay.

People carry the flats in their tote so that they can know. Just wear a little cute kitten heel or something. Like, don't wear the stilettos with the pointy toe that are going to kill you after an hour.

Just wear like a practical but pretty heel, you know, don't carry your like ugly flats in your bag and you're like changing.

No, that's like, not even a real. A real New Yorker too would wear the heels and like suffer through. I mean, that's like kind of a rite of passage when you're a New Yorker.

I mean, I walk everywhere. I don't walk in in heels, but like, I would never go somewhere in sneakers or like change into my sneakers at an event or something. Hell no.

Yeah, not happening.

I'm sorry. Go home. Like, yeah, if they're that bad.

Yeah, like, put it to bed.

Somebody told me about a woman who was 90 who wanted to wear heels. Her feet, her. You know, you lose the padding on your. As you get older on the bottom of your feet. So, like, people do all kinds of things.

But this woman would go and have someone shoot Novocaine into her feet so that she couldn't feel them so that she could go out for like dinner in heels and not be in pain.

I was like, oh, my God. I'm kind of obsessed with her falling.

All over the place. Like, sorry, I just had no vaccine shot. But don't my, don't I look great in these heels?

You know what? I gotta give it to her for the commitment. I mean, she is committed to her stuff. Yeah.

I mean, it's not like I don't get shot up in other places for other things to look good, like. Easy.

Yeah. We always need a little something. A little something something. I. I'm a. I'm a fan of it, too.