Gen X Vs. Millenial Vs. Gen Z Menswear Debate | Off The Cuff

Among the tenets of classic style is dressing appropriately for your age and also dressing according to your personal style. So, how are these principles interested by men from different generations? We talk about menswear and more through the lens of Gen X, Millenial, and Gen Z gents!

Video Transcript [Lightly Edited for Clarity]:

[Raphael]: Welcome back to the Gentleman’s Gazette. Today, I have James from Gent Z. Thanks for coming.

[James]: Thank you very much for having me, mate.

[Raphael]: And Antonio from Real Men Real Style. Now, I’m a Millennial, you’re a Gen X, and you’re obviously…

[James]: Gen Z, yes.

[Raphael]: So, that’s what we’re going to talk about today. Generationally, so what do you think defines your generation, stylistically?

What Defines Your Generation Stylistically?

[James]: I think we, as a generation, experienced some unusual events—most notably, the pandemic and the subsequent lockdowns that have really shaped what our generation is and I think our stylistic choices are also influenced by what happened to us. So, I think really we’re the first generation—if you like to dress up—we’re the first generation who only has to dress up because we want to. Very few people of our generation have to dress up for a job; unless you’re in, like, one or two perfect professions, it’s really not necessary for us.

Dressing up is what you do at a party, to the races, to the wedding; or just because you like it, you want to go to the club and wear that double-breasted, red suit that looks great and catches people’s attention. But, that’s people who are into our world.

For a lot of other people of my generation, style is a little bit less of a big deal; some people put a bit less thought into their presentation.

James, gen z

So, I think it’s divided into two camps, but I think we have the most ownership and ability to be individual with our style—compared to the previous generations. 

[Raphael]: That’s a good point. There are fewer forced conventions or dress codes, right?

[James]: Absolutely, yeah.

[Raphael]: Nice. What about you? What do you think, Gen X?

[Antonio]: You know, I grew up in the 80s and 90s. So, we saw from, you know, the 80s, the big shoulders, all the power suits, and things like that, going into the 90s; the rise of grunge and the styles there; and then, you go through the 2000s, you see… Who was it that was wearing all—was it Browne? The guy was wearing all the small, tight suits that looked like they were too short? 

[Raphael]: Thom Browne.

[Antonio]: Thom Browne. And then, after that, we now are going back into loose, heavier clothing—that seems to be the latest fashion. So, I think that, you know, a lot of people Gen X and beyond, we start to, you know… If you’re in your late 40s, 50s, 60s, you’ve seen a few things. You’ve seen styles come in and out, and you’ve heard about this maybe when you were younger and you realized that there’s really nothing new under the sun.

You know, the point about that your generation has gone through some interesting things—I think, every generation has interesting times that hits it, and you realize that, yeah, at the end of the day, we all though have to get dressed because if you walk out naked you’re going to get arrested, unless you live in a nudist colony; and it’s just something a lot of Gen Xers, I think… Yeah, they’ve seen enough and, hopefully, the ones that are a little bit smarter start to leverage style to, you know, send the message they want to send.

[Raphael]: I mean, you know, for me growing up, it was this like—wow, there’s this time when everything was skinny.

[Antonio]: There used to be the word “metrosexual,” and you never see any… No one’s using that word anymore. So, it definitely, you know, the younger… And one thing I have to give credit to Gen Z and maybe the Millennials, you guys started it, but it was something that men really did start to pay attention to—the way they started dressing. When I started writing about men’s style, you know in late 2007, 2008, those words were being used. The trends in Google for what we could see were all going up. Now, I think they’ve maybe peaked and that could be a demographic issue as well.

But, yeah, a lot of men now just… It’s normal to be able to go in and, you know, if you go to Target or any box store and you see all these options in grooming, which were not there ten years ago and definitely were not there just twenty or thirty years ago. You had just a few fragrances for men being put out there. You know we talked about Polo Green, which we smelt earlier, or some of these other classics. But, no Baccarat Rouge, it seems like, for men, you’ll every single month, you get more fragrances drop than there were released in a single year back in, you know, 1996.

[James]: Those gender boundaries have gone with a lot of fragrances as well, especially the high-end fragrances like Baccarat Rouge, equally worn by men and women. And you see that in the mainstream with clothing as well—more unisex clothing than ever before. I think with classic style, we understand that it doesn’t quite work when it comes to shoulders and proportions. But, in the mainstream, that’s quite a big thing now. The rules of gender, those barriers have definitely come down. And like we don’t use the word “metrosexual” anymore, but when I was growing up, especially as a kid in England around 2007, 2008, that would be like David Beckham was the pin-up of a metrosexual man, who takes care of himself. But, now, that’s kind of the base standard, really. You know, the skincare and putting some thought into your clothes.

[Antonio]: Yeah, who’s the one actor? The French… Timothée Cha… yeah yeah I think he’s 

[James]: Timothée Chalamet.

[Antonio]: Yeah, I think he’s done a really good job, you know… Even Austin Butler, you know, in the roles that he plays. I do think one problem with Gen X is that— and I think that this is just anyone that ages, in general—you can become rigid and, I think, what marks something as young, whether it be a plant or a human being, is your flexibility—in your ability to bend.

[Raphael] It extends to stuff like make-up even, right? Like makeup—growing up, I didn’t know any man who wore makeup, right? There was also a time, I remember, in school, right, if you want to express displeasure and say, “Oh! That’s gay,” right? And we’ve just moved away from that, and it’s a good thing, right? Like, my six-year-old at school, if people would say, “Oh! This is gay!” You know, this would be a big thing, and I think that’s a good direction.

But, it was funny, when I first, you know, showed Teresa the corrective cosmetics for men, right? So, they’re still not makeup. She was like, “They’re only three shades. What are they doing,” right? We wouldn’t have like 50 shades, so we can get exactly right to our skin tone. It’s still early days for men, but more men are wearing it. And it’s still more… They don’t wouldn’t go out and say, “Oh, I wear makeup,” or sometimes, you see men very… You can tell they’re wearing makeup, right? Eyeliner and whatnot? But, yeah.

[Antonio]: I still think there’s a lot of men that would reject that. But, I think, when you look at history, men have, you know, you may not call it “makeup,” but, if you look at war paint, if you look at camouflage, if you look at… Men use face paintings to signal to, you know, in baseball, they black under the eyes. It can be used in a functional perspective to either get rid of glare. But, yeah, the idea of using it to be able to cover up a pimple, perhaps, that—let’s face it—many of us, when we were teenagers, you know, forty years ago, it was something that did bother you—when you had that big pimple, and you knew you were going to see the girl that you liked. 

So, I applaud the latest generation if they’ve got a fix for something that, wow, we didn’t even have that solution forty years ago. That’s great! Not necessarily something you… And that’s the thing, with all these options, you don’t have to take them all. You can simply pick and choose and go with what works for you; and it’s becoming a lot more acceptable for people to choose their own path.

What Item Did Your Generation Popularize?

[Raphael] What would you say would be one item or a defining item that you kind of associate with your generation? Like, what did Gen Z bring to the world? And if you need a minute, that’s fine. Do you have anything?

[Antonio] Let me see…

But, if you look around, everyone’s already wearing what you’re wearing. Is that really your style or are you caught in a fashion trend? And so, I always challenge men to take a step back and can you change it? What message do you want to send the world with your clothing?

[Raphael] And then, you know, at one point, we were all younger. As you age, there’s a tendency that you kind of keep that same hairstyle, you know; you don’t evolve, so to speak. You just wear what was hip when you were young, and it dates you very quickly. You can immediately tell like, “Oh, this person must be that old because they’re wearing this,” which is obviously not.

[Antonio]: If you’re wearing the same Affliction jeans that you picked up or the same styles, yeah, it was popular fifteen years ago. But, yeah.

[James]: I haven’t heard of that brand, actually. [laughs]

[Antonio]: See, it’s a little bit. Yeah, it was before your time.

[Raphael]: So, what do you think about it?

[James]: Pieces from my generation?

[Raphael]: And it’s like a direct response almost to Millennials. Because Millennials were skinny everything, right? And then Gen Z or the kids of Gen X, right, so you have an 18-year-old? 

[Antonio]: He’s 19 now, yeah.

[Raphael]: So, you’ve seen that, right? And is he kind of aspiring to your style or is he like, “Dad!”

[Antonio]: No, he’s casual. Does his own thing. But, his clothing, you know, fits him well. I mean, a lot of these younger people as well, they realize that if you wear the right clothing, it can show off the time that you spend in the gym. So, my son, he has, you know, he has a drop, he has a taper, you know, with his build; and so he’s able to show that in even his casual clothing. Because when, you know, back in the 90s—you know, it was pretty rare even in the early 2000s—to find a shirt company that was actually making shirts specifically for men that are fit. 

Now, you find companies that are making clothing for men that are large, men that are modest. They’re out in New York… Gosh, drawn a blank here. But, you see brands, you see entire companies built around a body shape, and that’s actually pretty useful, especially if you’ve got a hard-to-fit body shape and you no longer have to pay the tailor tax.

[James]: The internet makes that viable as well for a business to operate. If you had a brick and mortar store for men under 5’5″, you would have almost no luck.

[Antonio]: You would only have to be in a big city like New York and that’s where, traditionally, they existed, you know? So, there was a small man store over in Los Angeles that I knew. You could be out in, you know, Las Vegas and go see Nudie Cohn if you wanted a rhinestone suit.

But, you know, he had his market in that area. Now, you can have these niche little stores and sell them to the world, and you can go to Etsy, you can go to eBay. And eBay is, I think, still a great place, especially if you want to escape modern fashion or the trends of your day because then, you can look through history and just grab pieces that work for you.

[Raphael]: And, I mean, stuff comes back. It’s almost a bit like, you know, sometimes, we will say “cultural stagnation,” where the music we listen to is 80s; like the clothes that are coming back are a lot of 90s inspired; and people want the original ’90s stuff. ’90s Polo, you know; 90s Reebok; 90s Nike. Whatever it is.

[James]: Weddings only, yeah. You’re right.

[Raphael]: In England, right, for weddings. But, here, for weddings, I mean… I think people are… The dress shoe is no longer required.

[James]: Interesting, yeah. I think from my generation as well, we’ve borrowed a lot of things from the past and, I noticed with guys who like to suit up, double-breasted is very popular among my generation. I’m wearing one right now, which is kind of an 80s thing, especially, you know, if you have a padded shoulder and kind of a more relaxed fit. So, I think people are playing on that.

We were also talking earlier about, you know, gender boundaries and people going a bit more feminine or androgynous.

[Raphael]: And, I think, you know, it’s okay if you’re a man and you’re like, “I don’t like suits and that’s not me and I don’t wear that,” right? Back in the day, it was like, for an interview, I have to wear a suit. This is the standard; that’s what’s acceptable. And today, it’s like, well, what is the company culture like and and do I fit in there and I’m not trying to be someone I’m not? Cause you can always see if someone loves wearing suits or if they’re wearing a suit because they have to. I mean, as someone who’s interested in that, you can immediately see what’s happening.

[Antonio]: Well, James, hit on a really important point. You know, the advent of the internet and making you know frictionless information that we can have quick access to. So, that question about what’s going on in that company with the culture, you can actually go on and you can see people, you can see pictures of, you know, how to dress if you’re going to an interview. Not just at Google, you know, maybe in California but maybe you’re going to one of their satellite offices in New York City. So, it’s like, “Okay, it’s still the city, but it’s going to be for this tech company,” so how are they dressing there? And you can read five reviews, which that information wasn’t available or not in that form, you know, in the 1990s, even early 2000s for most people at their fingertips.

Yeah, so, you know, there were probably the rules throughout the ’90s, throughout the 80s, early 2000s were more rigid. They were also passed on through pamphlets, through written materials, and oftentimes, word of mouth or you would have to call to get that information  

[James]: Yeah, but I’ve been for job interviews before I started doing this, and I would turn up and the creative directors wearing a sweatsuit; and I kind of researched before so I knew he would be, but I would have to deliberately dress even more casually than I would at home to try and fit with that company culture. So, it’s almost gone in the reverse these days.

[Raphael] And, you know, I think people can still be uncomfortable, right? Sometimes, what I hear is like; when I dress up like that. They’re like, “Oh, you make me look bad,” right? And that’s their kind of first reaction—they get a little more defensive. They’re like, “Man, I feel like I need to dress up because of you now,” and it’s almost like a, you know, a certain amount of gap thinking, where I’m like, “Hey, you are setting the tone and you’re doing this to make me look bad.” But, in reality, I don’t choose my clothes based on how you might feel, right? It’s more like an internal…

[Antonio]: I think that almost transcends even generations. That’s just human nature. As animals, we want to fit into a tribe and we want to look the same; and so, if we had somebody in the 1980s and we’re all in suits and somebody were to walk in in sweats, you know, you’re making… What’s going on? Even if he were to be in a position of power, it would make everyone feel or make us look at him as if he’s out of place. And yeah, it’s something that you now have to be I think a little bit more in tune because everyone thought it was easier that we have more choice, but it adds a layer of complexity because now you have to do the research and you really have to know the situation you’re walking into.

[Raphael]: And what I’ve seen, too, is like, lately, it’s this idea of having a uniform, not thinking about it. Like, I read about a woman, and she said, “I only wear, you know, black skirts and black boots and black top,” and has a very few items and just like, “I don’t need to think about it and it has become my style and people kind of recognize me for it.

I think Obama did that, too. He’s like, “I don’t want to think about this stuff.” Yeah, just simple and then, there’s the people who are like, “Man, I want to kind of express myself through that,” and I think this idea of expressing yourself through clothing is definitely more prevalent now than before.

[James]: Yeah, well, it really can be art or it can be functional. It has to be somewhat functional, but for some people, it’s kind of like, “Do I eat the same food every day because it’s easier for me to prepare and I don’t have to think about it?” or “Do I take the time to cook and prepare and enjoy it really?”

Is There A Prominent Designer From Your Generation?

[Raphael]: That’s sort of creativity, too, right? So, would you say there is a defining, you know, designer from your generation?

[Antonio]: Tommy Hilfiger—90s, right? Ralph Lauren—more 80s—late 80s. What about for your generation?

[Raphael]:  I mean, if you look at it from an overall aspect, I think Tom Ford had a big impact, right? I mean, he started at Gucci, and then he started his own brand and did his like cologne line and stuff. And I’ve noticed people have been saying, “Oh, you know, I wanted to be like Tom Ford.” And I think something that started maybe earlier was, you know, there was Zegna, for example. It used to be just a cloth manufacturer and then, they started, you know, doing everything—doing the clothes, delivering that to people. So, I think if you go to Nordstrom now, you know, they have these types of brains, too. Yeah, but Tom Ford as a designer personality, it’s probably would say the biggest one.

[James]: So, idiosyncratic as well with Tom Ford that it’s such a great adjective to describe something else, you know? I’ve even said that about one of your fragrances—that this reminds me of Tom Ford. It’s not even a specific Tom Ford fragrance that it smells like. It’s just that’s almost the bottle that I’m imagining when I’m wearing it.

[Raphael] But, if you think about it, he did well—and so did Ralph Lauren, right—they had this kind of visual identity where they brought people into a certain look—a certain style. Like, you associate being someone when you put that on, and I think he did it well. And there was also that, you know… Wasn’t he involved in a movie? Tom Ford directing it? You know, “Single Man.” Yes, so it was like popular culture through clothes, cologne, movies…

[Antonio]: The partnership with James Bond.

[Raphael]: And think about that, right?

[James]: Yeah, I wonder how many people notice sometimes, yeah.

[Raphael]: I mean, sometimes, it’s hard not to notice because it’s like this logo and this logo—that Montblanc pen, you know. Or you even notice in, like, you know, these detective shows in Britain, they’re all driving these really nice BMWs all the time, and it’s just funny.

[Antonio]: And there’s some pieces that are iconic, and they didn’t actually even pay to be there. I think Hamilton Watches has done a good job, you know, with—what was it—you know, Christopher Nolan and—what was it—”Interstellar.” The Murf. You know, that was—he just needed the watch and actually, they made a specific one for him. But, I don’t think they paid to be in that movie.

[James]: I was talking with a friend of mine the other day about Jack Daniels with Sinatra. That’s an invaluable product placement of a lifetime that I don’t think he ever got paid a penny for. You know, imagine having somebody like Sinatra associate with your product for free and then continue in the 80s with Mötley Crüe and those kinds of bands. So, yeah, I think it applies to pretty much every product.

[Antonio]: Yeah, same with sunglasses. Was it Ray-Ban? The Aviators with MacArthur landing in the Philippines. I mean, so yeah, the right product in the right place. But, definitely paying for placement is more common. So, in Gen Z, what is a brand that is up and coming?

[James]: I think Loro Piana has been a big one for the last few years, and obviously, it’s way out of the price range of most people, but their designs have influenced what’s in H&M, what’s in Zara, what’s on Shien even; and actually, I think Ralph Lauren as well has been a bit of a defining thing for my generation. You know, the Ralph Lauren store in Chicago or in New York is full of people my age. Even though they might not be able to afford it, they want to buy into that brand and the old money trend has been such a defining fashion trend of our generation.

[Antonio]: How do you feel about the resurgence of—what is it—Abercrombie and, yeah, those guys. I was in their Tokyo store and I was amazed. They’ve totally rebranded themselves. They’ve got everything. It just feels…

[Raphael]: When did you go last?

[Antonio[: A year ago.

[Raphael]: Cause it started out like British, traditional, hunting outfitters; and then, I remember when I was younger, people stood in line in front of their stores and everything smelled like…

[Antonio]: It smelled fierce.

[Raphael]: And I think the CEO was known for his flip-flops, right? It was that thing and then, they kind of were vain in popularity. And now so now they’ve…

[James]: I would say that the brand identity isn’t as strong as it was during that peak of you know 10, 12. I was a kid at that time, you know?

[Antonio]: I saw them improve all their quality, essential pieces, and the logo isn’t as big as it used to be. And I think, people…

[James]: It’s not very cool anymore, that’s why

[Antonio]: People have come back in, and they’re just like, “Oh, this is good. It’s a basic. It fits well. When I was at the Mall of America, and this is actually just a few—you know where that’s at? Their store over there was packed. We went to do some just last minute Christmas shopping. 

[James]: I’ve bought some pieces from there—just linen shirts for summer or shorts. The quality is not amazing, but you can get some quite classic styles from there—for the price. If you’re a young guy, it’s not too bad.

What Do You Think of Brands Like ‘Supreme’?

[Raphael]: What do you think about brands like outside of more of the classic realm—like, you know, Supreme? Or are there like… What are the brands for Gen Z out there?

[James]: You know, you’re kind of asking the wrong person, wearing what I am. [laughs] I see that as a bit of a cult, you know, around brands.

[Antonio]: The idea of the hype beast, you know, and him—him or her—you know, standing in line and being a part of limited runs, pieces like this. I think this, when I look at your generation, especially the street, like Bathing Ape… You know, it’s just like these guys, it’s interesting. They’re paying crazy prices for it. Not my cup of tea, but to each their own, right?

[Antonio]: You know, to their credit, you know… 50, 70 years ago, the down payment on a house was something that you could actually maybe get on one income. Now, you have to have three incomes.

[Raphael]: I think that is a true problem, right, where it’s like, “Hey, the percentage of income needed for down payment seems so kind of out of reach that I think it’s similar with wrist washes, right? This kind of like, I’m wearing that Rolex but I will never be able to buy that car or this home. So, I’m not even thinking about that, but I’m still treating myself.

[Antonio]: Well, that’s a brand, you know? Getting back to what you talked about with… I mean, just before we’ve seen recent inflation, the inflation that happened because of Covid and simply because things couldn’t move around the world as freely as they used to, when we see you know brands—you mentioned Rolex—all of a sudden, used Rolexes all of a sudden shooting up in price. Used cars, as well. But, you know, it became almost like a currency. I don’t know who was buying all those used Rolexes. Maybe it was, you know, you Millennials over there.

What Items From A Specific Generation Do You Wear?

[Raphael]: Is there anything in your personal style, where you’d say like, “Hey, this is a Gen X item that I truly wear or this is a Gen Z item or Millennial item that I really like?

[Antonio]: I still like boxer briefs. Not… And like the looser boxer I still have a love for them, but I’ve now gone down…

[James]: Women hate them so…

[Antonio]: Yeah, the original boxers I love and still remind me of the 90s, but I’ve now moved to the boxer brief. And yeah, no turning back there. What do you wear?

[James]: Commando. Yeah.

[silence, Raphael and Antonio doesn’t get the joke]

[Raphael]: Yeah, I like boxer briefs, too. But, yeah, tidy whities, I still have a few of those, but I have them in dark when I go for a run. You know, I just want something that gives me a little bit more support.

[James]: The images.

[laughs]

[James]: I’d say I don’t really feel like I represent my generation on the mainstream when it comes to style. I think just wearing suits and blazers for the love of it and for the fun of it is kind of definitive of my generation. You know, I go out for dinner with my friend and we’ll just text each other like, “Want to give it the full treatment tonight,” you know? And that’s just for fun. It’s not because we’re going somewhere fancy or anybody else is going to do that. It’s just because we want to do it.

[Raphael]: But, did you notice, like, when you put on a suit, you walk differently, people look at you differently?

[James]: I feel like now I do it so often that if I were to wear casual clothes, I would probably not feel very confident compared to how I normally do. Yeah, I wouldn’t quite feel like myself. So, I find if I wake up one morning and I’m just, you know—you some of those days—you just think, “I’m not really feeling it today.” You know, I’ve got a headache or whatever—get dressed up, and it’s medicine.

[Raphael]: Nice. I think, for me, it’s like boat shoes. During the summer, I wear a lot of boat shoes and you could say, you know, they’re really older or like, you know, some of the sunglass designs— like, you know, wayfarers, aviators. I mean, these are all older styles and they go in and out of popularity, but to me, like, you know, Top Gun aviator—it’s more so than MacArthur. But, I also didn’t grow up here, but that’s kind of the picture that sticks with me.

[James]: That’s an interesting point because we not only have three generations here, we also have three different nationalities but all living in the US.

What Do You Think of Sunglasses & Eyewear From Your Generation?

[Raphael]: Yeah, so what do you think of eyewear and sunglasses for your generation?

[James]: You know, typical glasses have become much more of a big deal in the style world, you know? I’m blind as a bat but I wear contact lenses. But, for people who enjoy wearing glasses, I think people are having a lot more fun with that. Also, in the more sartorial community, it’s another accessory. If you choose a good pair of glasses, it’s just like a boutonniere or a pocket square. I think, in previous generations, glasses were almost seen as more of a medical device, and like if I look at what my parent’s generation would wear, they kind of just…

[Antonio]: Yeah, we’ve seen companies like Parker come out and just be able to build huge brands and to give tons of great choices. You can walk into their store. I was in the New York store, and I mean, it was just… The selection was amazing and the nuance and the styles, the colors. You could have a lot of fun with that.

[James]: Yeah, you could even wear like a slight orange to match your pocket square and your glasses. Yeah.

What Are Brands Doing Differently To Adapt To Today’s Technology?

[Raphael]: And I would say like this kind of, you know, D-to-C brands, that was something that really came up more Millennial, Gen Z time. In Gen X, the D-to-C brands, there was no internet so it was really hard to do that.

[Antonio]: 2007, 2010, you know, 2013—we saw all these brands pop up, and I think both of us, you know, in putting out content at the time, we saw many of these brands in their early phases because they would approach us to do advertising or to be able to… They understood the power of, “Hey, you guys are engaging with the audience. Can we work through you to be able to reach them?” So, it’s been cool to see some of these brands.

I mean, remember Bonobos just getting started? And, you know, they were just pants. You know, Spaly and the other gentleman—the two Founders out of Chicago business school. You know, one of them was Andy Dunn was the tailor or his mom was a tailor; the other is a straight business guy—coming together, making these pants. They, you know, get rid of what they called “khaki diaper butt.” So, they solved a problem, and I think that that definitely is a mix between your generation—maybe a little bit of mine, you know—but these guys, seeing a problem, creating a clothing brand that solved that specific problem, and then once they’ve got their one product—as we were talking about earlier— then serve customers with other items.

[Raphael] To kind of upsell them. I also think that the way to do business has changed, you know? Like, traditionally, if you go to Europe, you know, it was like, I have my small business and it’s more of a self-employment-type situation, you know? I make enough for my family, but I don’t have this aspiration to create this worldwide brand with franchises and all that stuff. And then, you had like Warby Parker or Allbirds or whatever, right, where they aggressively pursue that market share. But, recently, I looked at a bunch of D-to-C brands and their kind of balance sheets, and it looks like they’re losing millions a year. It’s incredible.

[Antonio]: There’s all different types. I mean, there’s the kind that are taking venture money, and they’re making the bet that they can acquire enough customers or grow big enough that they will be acquired and somebody at some point can figure out how to make the money, which as a bootstrapper, I’m always just like… You know, we talked about this with what you guys are doing for Fort Belvedere. You’re trying to build a brand that’s going to be around, so it’s your life’s work. It is a mission company that wants to grow slowly and have this deep relationship with the customer; versus, yeah, growing big, getting acquired, and then getting kicked out, but having your golden parachute of $20 million or whatever.

[Raphael]: You know, I get that concept of let’s grow something big, let’s get the market share, and let’s sell then. But, I also think it can be hard to just, you know, create a company where the culture is that we spend, we spent more marketing; but eventually, you got to make a profit, and it’s going to be hard culturally to just say, “Okay, now, we’re going to be profitable, you know? And it seems like that’s…

[Raphael]: Yeah, but, I mean, it’s surprising for me to see. I’m curious how all these big D-to-C brands that we know today will fare in 10, 20 years from now. Because if they don’t make money at a certain point in time, the investment will probably dry up—that’s my guess.

[James]: I would like to see more D-to-C from my generation because, with e-commerce, for my generation, it’s very easy to do it with other people’s products and dropship and do your marketing on TikTok. It’s very hands off and you don’t need much money upfront, but as a result, we’re lacking a little bit of that entrepreneurship and innovation in terms of new products and quality products. I think that will come in the next few years. You know, that kind of the ceiling for being Gen Z is my age, 26, so it takes a few years sometimes to develop that acumen and an eye for the right product. But I would like to see a bit more of that from my generation.

What’s It Like Living in The Internet Age?

[Raphael]: And do you think that… You know, I grew up without the internet. I knew what the world was like without the internet. You did, too. When you have Instagram, when you have TikTok, there is more of “Oh, I see this, all these people have these amazing lives and I’m here, you know, working hard and my life sucks.” Like, is that something that you senior generation, where there’s a lot of aspirational thinking or like how does that…

[James]: Definitely a lot of aspirational thinking. I think I was lucky that I had a childhood without too much internet or social media, you know? I still remember being on my computer, my mom saying, “You need to get off the internet so I can call your grandma,” but you know, by the time I was 12, 13 it was a very everyday part of my life. Yeah, I do see that. I think my generation is more money-centric as a result of this, and people aspire to have these lifestyles that they see on reality TV and on TikTok.

[Raphael]: Like, if you ask, you know, what would you like to do as a job, right? People say YouTuber or influencer. Not like a firefighter, you know?

[James]: But, we’re all YouTubers, so, you know, I don’t blame them. It’s a good job, but, you know, I came from a journalism background, which, as a skill set, is quite similar to what I’m doing now. But, to be able to do the same thing using the same skills but have my own thing that I’m creating and work for myself and build something that I’m proud of, it’s much better than working for somebody else, who throws you a salary every two weeks. Yeah, so I understand why people are into that because that’s the gold rush of this age—is the internet. So, I understand why people want to get involved in that.

Do You Have Any Prejudices Against Other Generations?

[Raphael]: Yeah, would you say there are any prejudices that you have against the other generations? Sometimes, I feel like, you know, people are like, “Oh, Millennials are lazy or like that kind of stuff.” Is there anything that you found you know to be true or not true for yourself?

[Antonio]: We were having this conversation earlier talking about how every generation—you go back to Roman times, you go back to the 16th century— I was reading, you know, like a newspaper from London like the 1840s, and they’re saying this generation that’s coming up is horrible. So, this has been said again and again, and I think that, again, if you’re Gen X—you’re 50, 60—you should… I think a lot of us have, maybe… We look at the negative, but there is so much good with Gen Z and how hard a lot of these young people are working. So, I don’t… I hear it. Sometimes, you think about it. But, the reality is, you know, the only prejudice I would say is that they don’t maybe know how lucky they do have it and how much choice and how this is…

I mean, I can’t think of a time I would rather be alive and be starting off than right now because you’re going to hear all these people that are doomsday, you know? Saying that, “Hey, we’re never been…”

We’ve been much closer to nuclear war than we are now. We’ve also been much closer to the environment… I mean, I think we just have so many capabilities, so many options. 

Antonio of real men real style

The biggest challenge this generation faces, and maybe the one stereotype that isn’t as common, but I think that they have, is that they need to realize that they have… You know, with these infinite options, they just need to make a choice and maybe be happy with the fact that they’re not going to be able to get everything. Maybe this generation has grown up believing that they can have, you know, all of this money, that they can have all of this impact, that they can see the entire world, and I don’t think that’s possible. There’s too much of the world out there. If you’re going to chase money, it’s hard to chase purpose. Or you know, you can do it but it’s hard. And I think, this generation, they’ve got to learn that maybe, you know, choose one and go after it—you can’t get everything, but you can get anything that you narrow down your focus and go after. 

[James]: There is a decision paralysis that comes with that infinite choice, and I think with the aspiration thing, before you might have—you know, growing up in the 80s—you might have seen something in a magazine, you think, “Gosh, I wish my life was like that” or you know, you read Playboy and you imagine, “I wish I was this kind of guy.” But, then you close the magazine, and you forget about it. It’s not constantly around you.

[Antonio]: You were reading Playboy?

[James]: I read old Playboy all the time. It’s a big thing for my channel—big inspiration, yeah. [laughs] But, I think not only do people look at the generations below them and see their flaws, but also we look at the generations above us and see how they had it good. So, we were talking about down payments—that’s a big thing that my generation feels like they missed out on, affordable housing. But, also, you know, if you’re in the 70s, you had terrible inflation; born 30 years earlier, you’re in a war. So, there’s always something bad and good about being born in any generation, and I think some people’s personalities maybe gel a little bit more with certain things. Like for me, I wasn’t really a big social media guy until I started doing this. So, I probably wouldn’t have seen that as a big advantage until I found a way that it works for me.

[Raphael]: Yeah, I think there is a risk of like, you know, when you always compare yourself that you’re no longer happy with what you have; and even though on a grand scheme of things, you know, if you grew up in America today, just the ability to you know pursue what you want and you can still, you know…

[James]: Sorry. I do think it’s very easy to be comfortable in my generation without much effort, and that can be a bit of a curse as well. You could be a young guy who works from home, gets all your food delivered, watches video games, watches pornography, and that’s it—you’re like plugged into this system 24/7—and that’s not good. That wasn’t an option a couple of decades ago.

[Antonio]: Your generation, you have isolationism. It’s a huge issue that they’re facing. We talk about this loneliness epidemic, especially for men, because it is so easy to be able to cut things off. We’ve seen that, right, with AI. You know, talking about AI girlfriends, robotic girlfriends, and again, you mentioned this—and there’s a lot of guys that like, you know, “She’s not going to take… Not going to divorce me. Not going to take half of everything. I get it whenever I want. Sign me up.” And like, you see that, but you also realize that’s really sad.

[James]: Yeah, I mean the Matrix is kind of coming true 25 years later. Technology is just about caught up where it’s like, which world do you want to live in? Do you live in the real world or the artificial one?

[Raphael]: Do you think, like video games, it’s a bigger part now for Gen Z than it was maybe for Gen X or Millennials?

[James]: I think they’ve got better. I haven’t touched a video games console in probably 12 years. So, I don’t know from firsthand experience, but they must have gotten much better, and there’s much more community built into them now, where you can really just be sucked into this video game world, and you feel like… You know, it’s like, imagine you get a sample of food. It’s not the same as having the meal, but you’ve got just enough to be satisfied and feel like you’re experiencing something real. So, yeah, I would imagine with the video games of your generation, they just weren’t quite good enough that you could be so sucked into them for your whole life.

[Antonio]: If that’s a good thing in the sense of, yeah, we’re a very soft drug, you know? And you could enjoy it, it was recreational.

[Raphael]: You can buy virtual property.

[Antonio]: Or you’re speeding up the process, and you’re using, you know, these young people using their parent’s bank accounts to…

[James]: It’s exactly the same as another big issue for my generation—online pornography. In your generation, it was a photo in a magazine or your dad’s VHS that you found, whereas in my generation, it’s like virtual reality, virtual girlfriends.

[Antonio]: Easy access, right there. Any type of… 

[James]: Anything too easy is generally bad, I think, for any generation.

[Raphael] Yeah, that’s a good point. Well, thank you so much for talking about different generations and, you know, after all, I think it’s great that we still come together. And you’ve always been a great connector, Antonio, in bringing people together, and so here we all are.

[Antonio]: Gen X power!

[Raphael]: I think that’s more an Antonio skill than your generational skill. Just a you thing. But thank you for making that happen. You’ll want to check out James’s channel.

[Antonio]: It’s a good channel. Great channel.

[James]: Thank you.

[Raphael]: Gent Z. Real Men Real Style.

[Antonio]: That channel’s okay. This one rocks. (Pointing at Raphael)

Check out our Gen X guest Antonio’s channel (Real Men Real Style) and Gen Z guest James’ channel (Gent Z)!