Why Personalized Bridal Beauty Is Replacing “Instagram Face” | WDP Ep 77

🎧 Listen to learn:

• Why “Instagram face” is fading in bridal beauty
• What brides should expect during a makeup trial
• How bridesmaid beauty trends are evolving
• Why natural glam is replacing heavy contour and baking
• Where Cassandra finds inspiration for editorial bridal looks
• How to achieve timeless wedding-day beauty without looking overly trendy

What does modern bridal beauty actually look like now that brides are moving away from overly polished “Instagram face” trends? In this episode of Wedding Day Podcast, host Sonja Babich, CEO of Iron Diamond Media, and co-host Lauren Mang, Editor-in-Chief of Oregon Wedding Day and Washington Wedding Day, sit down with Cassandra Kennedy, founder and lead artist of Portland-based Cassandra Kennedy Beauty, to discuss the evolution of wedding makeup and why individuality has become the ultimate luxury in bridal beauty.

Known for her editorial-inspired, skin-forward approach to hair and makeup, Cassandra shares how her artistry was shaped long before beauty tutorials and influencer culture transformed the industry. Drawing inspiration from fashion editorials, films, flowers and natural light, she explains how she helps brides create elevated wedding-day looks that still feel authentic to who they are rather than copies of viral makeup trends.

The conversation also dives into Cassandra’s collaborative bridal trial process, the importance of skincare prep before the wedding day and how beauty trends are shifting toward softer glam, glowing skin and more personalized styling choices. She also discusses the growing movement away from perfectly matching bridal parties and how modern weddings are embracing individuality in both fashion and beauty.

Transcript

SPEAKER_00 0:00

Welcome to Wedding Day Podcast with your host, Sonia Babbage, CEO of Iron Diamond Media, a leading wedding resource featuring seven localized wedding brands across the country. Hi everybody, Sonia here with Wedding Day Podcast. We are here in Lake Oswego, Oregon. My co-host today is Lauren, editor-in-chief of Oregon Wedding Day and Washington Wedding Day, and the first time you all are meeting her. But we're sitting here with Cassandra Kennedy, and she's the owner and lead artist of Cassandra Kennedy Beauty. And she's been doing this for two decades. She's like before dinosaurs were here. And we're just so excited for you to meet her. I think I'm gonna have a lot of giggles when we hang out with her today. So, well, thank you for being here today and also you know making us look beautiful for the podcast today, too. Thank you guys. It's fun. I love it. So you've been doing this for two decades, you've seen a lot of changes in beauty. Um, but what I what I love is that you like the nowadays people are getting inspired from Instagram where you like were inspired by like magazines and fashion, and I think you still are, right? Because yeah, right.

SPEAKER_02 1:17

So I'm from the before times, the 19th century. But yeah, I when I was coming up, you know, we uh looked at fashion magazines and uh I love art, and uh we looked at you know, real people on the street, and there was no Instagram, uh lots of books and stuff, you know, and so there weren't any tutorials, you know, and you had to look at some of you look at like Jane Fonda's Barbarella, and they're like, How did they do that? And you had to just get in there and try to get that look, you know, or like uh Vermeer's uh girl with a pearl earring, you know, she just like incandescent and just glowing. Like, how'd they get that look? There wasn't any tutorial, and so I'm glad about it because it uh you find your own style and you really have an original way of seeing things, and now um Instagram is so fun, you get to see your favorite artist really like putting makeup on someone you never could before, but it kind of homogenizes everybody, I think. You know, the Instagram look uh everyone starts to look the same.

SPEAKER_00 2:42

I know you said that.

SPEAKER_02 2:43

What do you mean by that? Well, how do you think that everybody looks like? Like if you bridal, for example, if you just look at bright like I'll look at a bridal artist's page and they just all are kind of variations on a theme, you know, and the same with Instagram and stuff, they all kind of have this look. There's a little variation, but everyone's starting to look really the same, and it's disturbing. So I think the artists that I love and that have always loved they're from the before times too, or they're in a foreign country and they're just they're not doing that.

SPEAKER_01 3:21

So when a bride comes to you and she says, That's the look I want, that's the the you know, the sameness of it that she's interested in, how do you dissuade her from that, or how do you decide to like kind of push her maybe out of her comfort zone?

SPEAKER_02 3:35

Um, I don't want to push anyone out of their comfort zone, but I want to get to the essence of this person. Right. And so I want to see, you know, I have like a three-point matrix in my mind. There's her in her real life, how she does her own makeup when she's going out or something, you know, and then there's her inspiration photos and like the link to that, and then there's me and all my kind of original ideas for her, and so we've got to kind of mix those together and create something original for her. So um it's just a I allow a lot of time, and I tell her, like, let's just experiment with stuff, and we try lots of different things, and so it's kind of like you know, we're driving to a destination, and we kind of know like it's up there on that mountain, and but like how are we getting there? We don't know, so we'll go down little paths and be like, Oh, terrible idea, and we'll come back. Um, you know, and so by the wedding day, like, okay, we know exactly where we're going, but oftentimes we end up like I end up surprised, the client ends up surprised. Like, you know, we try four different lip colors and wipe it away, but the stain that those four left behind is so lovely, and we're like, oh, look at this. She's like, This is literally perfect. I'm like, okay, well, mix those, apply, and remove on the wedding day.

SPEAKER_01 5:06

So that's what's so fun about you know your job and your role in this. And like when you were doing my makeup, we were geeking out over a blush because I'm obsessed with blush, blush blindness, and you mixed a bunch of colors together for me, or a couple colors, which I didn't even know was possible.

SPEAKER_02 5:24

So me either, yeah, like just the fact that you're in there, like no so I don't label colors or like you know, this one is Charlotte Tumblry, fluffy girl, or whatever. They're just all in the palette, and I know which ones are shiny, which ones are more opaque, and you know, I experiment a lot, so I know like a little this, a little that, and a dab of that is gonna be like the perfect coral or whatever, and so you really get to know your kit. And I I don't have any eyeshadows uh labeled or in palette, they're all just there, and I know like this is a fleshy shimmer or this is like a cocoa brown. In my mind, I have them labeled, I know what they are, and um kind of break away from those. I mean, those are great for a consumer and stuff, like this is my color, yeah, you know, but artists I like when they it takes a while to have the courage to just break out of that and mix and match, and you know.

SPEAKER_00 6:32

You were saying like also like bridesmaids, like because of Instagram, like everybody looking the same, but also like a bridesmaid's kind of going it's away, like more individual looks are coming more in, or what are you seeing more with the like the bridesmaid's look?

SPEAKER_02 6:46

Well, I think um like back when I started it was so there was no option, but everybody matched, you know, and that was the norm, right? That was my that was me. Yeah, yeah. I'm guilty, yeah. Me too, and there might be like one had like a one strap or something, like variation, but everyone had the same color and material and stuff, and I think there's just been a rise of like individualism, and I think that I suspect that trickles down from the luxury industry where there are stylists to help guide you know the bridal party to have a cohesive look, but everybody's different, it's more exciting and more unique. But um, I still think there's a variety out there, you know. But like I I did a wedding on Saturday, and uh the bride was so chic, and she just said to the bridal party, like, you guys know it's like black tie, cocktail, wear whatever you want. I don't care. And she's like, I thought about giving them like guidelines, like colors and stuff, but she's like, they're all have a great sense of their own style, whatever. It was a real variety, and they all look great. So, you know, some brides have a vision, you know, and the wedding is a little more classic or something, and I I think you know, the bridal party looking a little more similar like matches the vibe of the thing, so it's kind of all over the board, but it's nice. I think back in the day you didn't really have license to do that, and now people are just doing whatever they want.

unknown 8:38

Right.

SPEAKER_00 8:39

Do you do you ever get in a situation like oh you are looking too much like the bride?

SPEAKER_02 8:44

Oh yeah, we had that on Saturday. Her sister was like, I want a slick back, and up to I'm like, Your sister's having that, and you look just like her, yeah. So, but I think it would look good on you. So the hairstylist was like, What if we just did a sleek pony coming down the back? You know, but you still get that slick back, and like she's like, Oh yeah, I like that.

SPEAKER_00 9:07

Do you still think that's gonna be in for a while? The slick back look. Um I'm like in the 90s hair right now. I'm like having straight, I'm like, thank god it's in again, you know, like not like such a tight like bouncy curls or the beauty waves, but do you still I think for some types of events and some types of rides, they that is their version of classic.

SPEAKER_02 9:36

Like this bride I'm talking about, she had a little bit fuller hair and stuff at the trial, and she I could tell she was just like, hmm, and I was also like, hmm, hmm. So, you know, time's up. You send her home, you're like, No, you're staying. Like, what if we do this or that? And then I just pull it really tight. She's like, Oh, I love it. And it really suited her face shape and stuff, that's not for everybody, right?

SPEAKER_00 10:04

You know, yeah, when you're doing those trials, like do you have a uh like a sense like do you want my opinion, or like because sometimes that's do they want your opinion or not want your opinion, or I'm sure it depends on the client.

SPEAKER_02 10:17

I think you have to make an atmosphere that is collaborative and open. So I don't ever express my opinion like, oh my god, I love it. This looks so good. Because they might look in the mirror and think, I don't like it though, and they don't want to hurt your feelings or something. So, uh, but if it's like a definite no, I'm just wiping it off. She doesn't even say I'm like, absolutely not, we're not doing that. But um, so you know, I'll say, Okay, we're gonna look in the mirror now, and then let's talk about what adjustments we want to make, or we'll check along the way. Let's look at these eyes. Are we feeling this liner? Do we want a little more wingy? Do we not like the wing? Right, so it's more like we, and you know, sometimes they're like, what do you think? I'm like, I like it, you know, it's matches your coloring nicely, you know. You could do a little more X or shear it up a little. So they're like, let's try that, you know. So I'm suggesting things they can easily hook on to, or make an atmosphere that they can express themselves, you know. Yeah, and I also say, like, okay, even when we're done, you know, you gotta sleep on it. Sure. And then we'll talk about stuff you think of later. Like, it was just too much blush, or like, I think I do want the darker lip, or whatever. And sometimes it's game day feel, that bride again. She looks so pretty and fresh and lovely, and she was like kind of on the fence about you know, individual faux lashes, very natural, and I thought she just looked good without them. And I showed her in the mirror and she was all delighted. And I said, Do you want to still do the lashes? Or you wanna just she's like, I kind of want to just leave it at like this, and I'm like, Alright, great, let's go. So, you know, sometimes they're just feeling something else. They're like, I want to do it X, Y, Z, you know, and I'm like, okay, let's do it. Yeah, so this isn't like a tattoo, even the hairstyle, sometimes it just change, you know. I want to have my natural hair pattern or what I'm like, yeah, let's let's get the curls in here, right? You know, that's totally fine. Yeah, but I think when I was first starting out, you know, because we go over and over in our mind, I'm like, okay, and then we do this, and then we do this, and we study the face chart, and we're like, that would just throw me off my game. Oh my god, what we're changing the lip. Oh my god, oh my god, right, and now I'm just like, yeah, girl, let's do it. So um, you know, it takes time to just uh let go of those things, and sometimes it's something I personally loved, and I'm like, goodbye, beautiful update. No one's ever gonna see that, but it was good, and that's you know, that's life.

SPEAKER_00 13:23

So, how where do you find your inspiration? Is it like Instagram or like who do you follow?

SPEAKER_02 13:28

Certain people I mean, I my favorite artist is on Instagram from the Before Times, Patty Dubroff, and I've taken her workshop twice, and uh she did Sophia Ritchie's makeup for her wedding. She's Margot Robbie's artist, so anytime you see Marg on the red carpet, you know, all the Barbie stuff now is weathering heights.

SPEAKER_01 13:54

So I'm like she's everywhere now, yeah.

SPEAKER_02 13:56

That's Patty's work, and it's really like skin forward, it's really beautiful, and she really shows restraint, you know. Like everyone was like, What foundation did you use on Sophia Richie? They couldn't wait to find out, and then she was like, I didn't, she didn't use any, and I was like, Yeah, I love that. So, um I you know there's a few artists that I love, but uh I most of my inspiration is from just being in the world. Like I love looking at paint chips in the paint store. I love like I went to a fabric store and I saw these beautiful Liberty of London fabrics, and I was just like, wow, and I just in my mind put that on someone's face. These like coral and aubergine patterns. I'm like, that would look so beautiful on a person, you know. Flowers, the color of flowers in nature, or just sometimes like I'm looking at my kids at dinner and just the way the light is hitting their face, and just it's just a natural highlight. I'm like I love that, you know. So I'm just like taking notes of all kinds of things and movies, I love fashion shows, you know. I think those are important to follow because they are ahead of the game. They're already, you know, bridal tends to be like a step or two behind. You know, because it has to trickle down. So if you want to see what's next and what you know, look at fashion stuff, yeah, for sure.

SPEAKER_01 15:37

Was this something that you always knew you wanted to do and you were were you playing with you know your mom's makeup when you were a kid?

SPEAKER_02 15:44

So my mom was a hippie and we lived like totally off the grid, but that did not stop me.

SPEAKER_00 15:50

I totally off the grid.

SPEAKER_02 15:52

Yeah, we lived out in the middle of nowhere, but I literally was like crushing up berries and dandelions, putting it on my friends and stuff. I think I just always was attracted to those things, yeah. And my grandmother was very, very glamorous, and a lot of people on my family are like, you just her like reincarnated, you know. But I didn't have that around me at all, and I still just loved it. I mean, I got jello powder and made a lip stain on my little six-year-old friends. I'm just like, ooh, that kind of orangey pinky, even just a popsicle, the way it looks on your lips, you know, and I'm like, Yeah, that orange, yeah, that looks so good. So I think, yeah, prom night, you know. I'm just like all my friends lined up, I'm going down the line. So I think I was always that friend, but I didn't think it was a real job. Oh, okay, you know, but I didn't know. I just thought you just sell makeup in Macy's at some counter or Avon or something, yeah. And so I was like, no, I'm not doing that for a living. But you know, it's like the call of the wild. Can't stay away after a while.

SPEAKER_00 17:13

Did you just go? Did you just make that home? Yes. Totally. So being like just again, skin forward with beauty, I'm sure you prep your your brides like how to do the prep the skin prep. Right. What what are your recommendations to get the skin ready to rock for your wedding day?

SPEAKER_02 17:35

Oh yeah. Well, I personally take a long time on the skin.

SPEAKER_00 17:40

Oh yeah, I noticed that today. I was like, What are you putting on me?

SPEAKER_02 17:43

That wasn't even a long time. I mean, if it was your wedding, but I learned that from Patty. She's like just put it all into the skin, and that really changed the look of my work, like kind of made it level up. It just everything will look good if the skin looks good. But um, you know, like our best friends that we never get to meet are the aestheticians. Man, I've seen people come with a literally a new face, and I'm like, what? Oh my god, it's just plump and you know, uh smooth, and and they're like, Oh, I had a series of three facials. I'm like, yes, but um, you know, everyone's different, and so I'm always I'll text you some wrecks, you know. Girl, you gotta buy XYZ. Oh, you need this, you need this, trust me, you know.

SPEAKER_00 18:37

I feel like just sexy skin right now is like the trend. Yeah, yeah, taking self like that self-care of feeling it at once. I mean, I've always been into it.

SPEAKER_02 18:48

Uh yeah. So it's fun to kindly to finally see like what we're into and what we're doing, like kind of come into the mainstream. Because we were doing that, you know, 10 years ago, and it was like sharpie brows and baking and extreme, you know, contour glam, and we're all fresh and skin focused over here. Like, sorry, we're not doing that.

SPEAKER_01 19:18

Yeah, we're not baking anymore.

SPEAKER_02 19:20

Yeah, but celebrities like Haley Bieber, you know, she had a real fresh look. Sophia Rich.

SPEAKER_00 19:27

They kind of like ushered that in to like mainstream bridal, and I'm like, Well, I totally'm excited that Smokey Eyes are coming back, so that which is what I asked for. Yeah, they're like, come on back. My college are coming up, of course. Oh my god, I love it. Yes. Well, thank you so much for coming on the podcast. Like, we could talk to you forever. That's fun. Thank you for having me. And just overall with this being thank you for being a great supporter too of Oregon Wedding Day. Oh god, I love it. I do. I think every trip now, the last two, I've been with you. I'm like, okay, you're kind of stuck now. Sorry, but I'm sorry.

SPEAKER_02 20:10

No, I love when you guys come and we need to show you more. Oregon's beauty.

SPEAKER_00 20:17

Well, you make everybody look beautiful. Thank you. Well, thanks everybody for tuning into what you need podcasts. We'll see you next time.