How Each Generation Approaches Style Differently

Welcome to The Who What Wear Podcast. Think of it as your direct line to the designers, stylists, beauty experts, editors, and tastemakers who are shaping the fashion-and-beauty world. Subscribe to The Who What Wear Podcast on Apple Podcasts and Spotify.

In this age of social media, micro trends can come and go in the blink of an eye, while some era-defining ones can get a resurgence with a new generation. Each demographic has its take on fashion, and some topics can get a little heated (team ankle or crew socks?). But even with some friendly debate, there’s no arguing that each generation gives inspiration to the next and that there’s always a cycle.

On the latest episode of the Who What Wear Podcast, we hear from our panelists about their different takes on generational style. Our panel includes our host and Editor in Chief Kat Collings representing the millennial POV, mom-and-daughter duo Faith and India Hitchon representing Gen A, celebrity stylist Tabitha Sanchez representing Gen Z, and trend expert and creator of the After School substack and podcast, Casey Lewis, representing both the Gen A and Z perspectives.

For excerpts from their conversation, scroll below.

Welcome to The Who What Wear Podcast. I am so excited for this episode because we’re doing something a little different today. We’re hoping to encourage some group chat energy with a panel of lovely people. We’ll start with Gen A. So, Faith, even though you yourself are not Gen A, you speak for them, and you are in a household with at least one Gen A person. Can you tell us a little bit about yourself and the type of content you create?

Faith Hitchon: I was inspired to create content about what I was seeing with my own daughter in an effort to process her growing up. I used to send text updates to all of my friends who are also in brands, and we would chat all the time. I’d be like, This is what I’m seeing. You know, This is what India is doing.

One day, I was sitting in a carpool pickup line, and I was like, Oh my gosh, I should just record this on TikTok, because all my friends thought it was hilarious that they were getting all these updates. And so I just did it, and then I just kept doing it. I like to give the updates that I’m seeing IRL and a lot of times it is in the carpool pickup line.

Next, we have our Gen Z representative, Tabitha Sanchez. Tabitha, tell us how you got into celebrity styling, who you’re currently working with, and how you sort of lean into the Gen Z aesthetic in your work.

Tabitha Sanchez: I got into celebrity styling when COVID hit. My younger sister suggested I download TikTok, and I realized there was this whole group of untapped talent who didn’t have stylists.

I reached out to a lot of them, and I started working virtually with them while I was still living in New York. Then I moved to L.A. and started styling, and I’ve gone from there.

I’m working with Hannah Berner. She’s a comedian. She hosts a podcast. She’s amazing. Chloe Cherry, Zoi Lerma, Quenlin Blackwell—a lot of the Gen Z girls.

To top it off, we have Casey Lewis, who authors the popular After School substack and hosts a podcast by the same name. Casey, tell us how you got interested in youth trends and internet culture and the content we can find on your platforms.

Casey Lewis: I have always been really interested in youth trends since I was a teen myself and was obsessed with teen magazines. I didn’t think about trend cycles then the same way I do now, but a lot of my interests were the same in terms of, like, Oh, they’re wearing a chunky gold bangle here and here and here and here. What is this larger trend?

So about three years ago, I started After School as the trend cycle was just so accelerated with TikTok, and wanted a place to keep track of all this stuff. And so I had worked in media for a long time, worked at Teen Vogue, worked at MTV, and had always spoken to young people. But then, as I was getting older, speaking to young people was becoming increasingly hard, but also less interesting. But understanding young people and how to translate that for brands became more interesting, so that is a lot of the content that I make with After School.

Let’s dive into some quick, rapid questions about the fashion world, just to get a pulse of what’s the millennial, Gen A, and Gen Z perspectives on some of these things. Let’s talk about favorite brands to shop that are favorites of your generation. What are the designers that your cohort buys and/or aspires to buy? Why don’t we start with you, Faith?

FH: What’s interesting to me about Gen A is that, right now, there’s a lot of callback to brands that I think were really popular in the early 2000s. My daughter will get things from Edikted and then she’ll kind of tweak them in a Gen A way by cutting them or tying a string around the back of her pants.

And then Brandy Melville has been and always will be the reigning brand when it comes to younger generations. I think that it was true for millennials all the way down to Gen A, and then she wanted all these different styles of Dickies for this school year. So she was really, really into a lot of the cargo-style Dickies.

TS: [For Gen Z] it’s kind of similar to Gen A, like Edikted and Jaded London, but then there’s all of these smaller designers. Blondita is a really cool L.A.-based brand. Sabrina Carpenter just wore them in her “Taste” music video. The girls love Miu Miu. They love vintage. I feel like most of my clients and my friends go to the flea market every weekend.

CL: I think a really interesting layer is that the elder Gen Zers are very interested in designer and finding designer gems, while the younger Gen Zers are a bit more like the alphas in that they’re shopping at Edikted. Garage is a big one that came up in back-to-school hauls.

A lot of the baggy cargos [and] sweats from Hollister and Abercrombie and American Eagle, and this tube-top–and–cargo-sweats look that was very popular on back-to-school hauls seems to be a very big thing, and that’s mostly Garage, which I never even heard of until I started watching back-to-school hauls last year.

I’m curious about the people who are aspirational, style-wise, for each generation. [From the millennial POV] I’ve got some people on my list, like Zendaya, and then there are the throwback people like Audrey Hepburn and Princess Diana.

CL: I actually interviewed 20-ish tweens for a story in February, and I asked them all about their style icons, and none of them had names that they could provide. They would say, “Oh, influencers I see on TikTok.” There were no specific names.

I think many of them are so young at this point that they’re consuming YouTube. They’re not consuming The OC like we were. It’s not Mischa Barton. You don’t have that sort of name recognition.

FH: Yeah, I actually agree. I’m very curious what is going to happen to celebrities when Gen A really comes to fruition because they don’t really care that much about them. My [Gen A] daughter will catch on to certain dramas that are going on, but only if they make it onto TikTok. She will watch TV, but she doesn’t attach herself to celebrities in the same way that hyper-millennial culture was attaching yourself to what you were seeing on TV. It’s just very different for them.

They’re much harder to impress in some ways or they just don’t care as much. But I would say that, like the TikTok girls really do grab their attention. I think that they can just get really easily influenced by random videos that they see. They can find so many people whose lifestyles, manners of speaking, etc, they want to emulate. And it can change every day, too.

TS: I mean, it’s even the quick shift between “brat summer” and then literally overnight, they were like, “it’s demure fall.”

The quickness blows my mind. Just keeping up with the pace of the trends feels intense to me as a millennial. I’m curious how Gen A and Gen Z approach that speed of the trend cycle.

TS: In my experience with my clients, we try not to lean into any like trends or micro trends, because it goes away so quickly.

FH: There’s just a lot of inspiration coming out of a lot of creative and authentic people, and it’s hyper online. Younger generations are just getting inspired, and they’ll integrate certain things that inspire them into their organic style. It’s not like, We have to follow this right now. We have to make this a part of our personality right now. I have to change my whole look right now. You can pick and choose.

CL: I think with the nature of TikTok and social media platforms, young people can try on so many different identities or styles. Their identities are more fluid in many different ways.

Now we have Faith’s daughter, India, joining us for a few questions. What’s it like to have your mom report to the world what your generation likes?

India Hitchon: I really think it’s helpful for people who don’t really understand it or are a little confused on certain things because I feel like Gen A is a very complicated generation. It’s like some things mean multiple things at the same time. And so I feel like my mom reporting it on social media makes it more helpful for people who want to understand it a bit more.

Faith, what’s it like to watch trends from your youth come back?

FH: I definitely have had a couple of moments where I’m like, Oh, I’m definitely in my thirties, and I definitely have a middle schooler to see it all resurface. But I think for the most part, it feels fun. I think that there are parts of that style that I still really love, particularly the wide-leg jeans of it all. I never really loved skinny jeans. I like baggier clothes. I like a more casual way of dressing as well. So in some ways, it’s nice to have some things that I really loved come back.

There are things that we definitely don’t agree on completely. India cares a little bit less about matching your clothing tonally sometimes. And my millennial brain can’t handle that. I need a color palette to make sense of my outfit, but she’ll mix patterns, she’ll mix colors. She’s a little bit more playful with what she wears.

Who inspires you or how do you decide what you like in the fashion space?

IH: I get a lot of my inspiration off Pinterest. I feel like you can find anything. You can literally just search up “a cute outfit with black leggings,” and there’s gonna be a bunch of different options and styles.

Are there any people whose style you follow?

IH: I think there’s because there’s so many kinds of styles, it’s really hard to find. Because you have your people who are really coquette and really love the bows and the cardigans and the white and the pink. And then you have your Tara Yummys who like the stars and the black and the rhinestones. It really depends on the day.

This interview has been edited and condensed for clarity.