The Truth About Personal Style That No One Tells You

Want to see some funny stuff? Here is me as a baby. I wanted to be a train conductor. Here is me in 1985. I was going to play for the Boston Red Sox. Here's me in middle school. Here I am in my high school senior photo. Here's me at basic training graduation. Here's me when I first started. He spoke style. This is 2015, 2018. And right now, well, this is me right now. I'm still evolving. I'm still changing. And I'm still figuring things out. Yes, even me, the all powerful YouTube style god. If you've ever looked at your closet and thought, "When did [music] I stop liking these clothes?" or worse, who even am I anymore? Then this video is for you. So today, I'm breaking down why your style changes, what signals to look for, and most importantly, I will give you the exact road [music] map to use in order to evolve intentionally instead of feeling lost. The myth and why it matters. So here's the problem with almost every piece of style advice that you have ever heard. It treats personal style like a puzzle you need to solve. Find your style. Discover your look. Unlock your personal [music] uniform. All of that language suggests wrongly that there is an end point, a moment when you figure it out and you're done. But think about that for a second. I will tell you that there have been many times I have personally thought I've had it all figured out in terms of style. For example, when I was first getting started with hepoke style, just getting into tailoring, I really fell in love with the brand Reese. They had a variety of off therackck tailored pieces that I thought were somewhat unique. I like the simplicity and the modern cut. Just kind of hit for me, you know. But after a few years, I started to feel differently. I felt like the cut was too modern, and the fabrics and color ranges were boring to me. The brand itself just started to feel a little more youthful than [music] I was comfortable with. And what's interesting here is that a lot of the things that drew me to the brand in the first place were the exact same things that I started to question or started to feel differently about just a few years later. So, the truth is that finding your style is a [music] myth. And it's not just wrong, it's actually limiting your growth. Because here's what actually happens. You're not the same person you were 5 years ago. Your life is different. Your body might be different. Your daily routine has changed. Your values have evolved. Your confidence has grown. Your interests have shifted. If you've changed, why would you expect your personal style to stay frozen [music] in time? So, the real question isn't how do I find my style, it is how do I let my style evolve with me without losing myself in the process. The signals of change. So, let's talk about what's actually happening when your style starts to shift. Because most guys will experience this as confusion or even failure when really you're just getting new information about yourself. There are basically three types of signals that tell you you are undergoing a personal style evolution. Internal signals, external influences, and practical realities. First, let's talk about those internal signals. These are the gut feelings. You put something on and it just feels off. Not necessarily wrong, but you know, not quite right either. And here's what most guys do. They ignore [music] it. They think, "I spent good money on this," or, "I wore this with a ton of confidence last year, so what's my problem?" But that feeling you're feeling, that is valuable data. It might mean that your confidence has grown and you're ready for something maybe bolder. It could also mean that your lifestyle has shifted and the piece doesn't match your daily reality anymore. It could mean that your taste has simply matured and you're noticing things about the garment that you couldn't see before, or honestly, that your body has changed and the fit isn't working in the same way that it did before. The key is to not dismiss that feeling you're feeling, but to pay attention to which pieces trigger it and why they do. And here's a personal example. So, for the longest time, my absolute favorite jeans were the 484 fit from J Crew. And I can't even count the number of times that I have responded to someone in the comments here asking what particular jeans I was wearing. You may have noticed that I don't wear them anymore. They just started to feel a little too tight for me. both in terms of being a very slim cut, but also I got older and I wasn't that rail thin elite level bicycle racer that I once was. And I can very vividly recall when I made the choice that it was time to step into a different pair of jeans. I went to Macy's, I got some 501's, and I thought, well, this is [music] me now. And I'll tell you, at first they felt baggy, but the more I wore them, the more I saw myself in them, the more they felt like me. And now people are asking me in the comments about the 501s I wear. Next, let's talk about those external influences. So, these are harder to spot because they're more gradual. Maybe you've been watching different content online. Maybe you started following different people or spending time in different environments. Maybe there's been a cultural shift. For example, everyone's talking about sustainability now or quiet luxury or old money or oversized fits happen to be everywhere or vintage has become cool again. You're absorbing these influences whether you realize it or not. and sometimes they align with where you're already heading internally and that's when change begins to accelerate. The mistake is thinking you have to follow or resist these influences. Neither is true. The real question is does this resonate with who you are becoming. Now let's talk about the practical realities. This is the most overlooked one. Maybe your work situations changed a whole new career, different field. Maybe you moved to a different climate. Maybe you had kids. Your life makes demands on your wardrobe. And sometimes what worked perfectly in one chapter of your life becomes completely impractical in the next. A lot of guys feel like this is somehow cheating or compromising their personal style. But integrating practicality into your aesthetic isn't a compromise. It's a sign of maturity. And I'll tell you, the practicality versus style with a capital S dilemma is real. But here's the thing. The best style finds the overlap. It doesn't sacrifice one for the other. Your new rules. Once you accept that evolution is natural and you start to recognize the signals, something really interesting starts to happen. You start developing new principles or rules for yourself. Now, these aren't rules that are handed down by editors or influencers. These are your evolved style standards. The unspoken agreements you make with yourself about what matters. Now, let me give you the three that come up most consistently, including in my own personal style journey. The first is quality over quantity. At some point, most guys hit this shift. You stop caring about having more things and start caring about having the right things. And this isn't necessarily about price tag. It's about [music] intentionality, consideration versus accumulation. You start asking different questions. Will this piece last? Will I still want to wear this in 3 years? Does this represent who I actually am right now or who I want to be? So, going back to my Reese example, these were the things that I was thinking about at that point. I was gaining a better appreciation and understanding of [music] custom and bespoke clothing. And I started to wonder or question really whether tailored pieces from Reese were good investments for [music] me. I had started to feel like I was aging out of the brand. And if I wasn't going to wear it now, I definitely wasn't going to wear it in 3 years. And along the same lines, my tastes were starting to trend towards a much more classic and old school men's wear aesthetic. Which is a great segue into when the second thing that comes up, which is when a personal uniform emerges. Now, here's something that nobody tells you except me because I'm going to tell you. At a certain point, having infinite options [music] stops feeling like freedom and starts being noise. You start gravitating towards combinations that just work. Not because you're being lazy or uncreative, but because you've discovered what authentically represents you. This doesn't mean wearing the same thing every day. Allah Steve Jobs. It means you've identified your foundations, silhouettes, colors, and proportions that feel like you, and you're building around those rather than constantly starting from scratch. [music] The irony is that this actually breeds more creativity because you're experimenting within a framework that already works rather than reinventing the wheel on a daily basis. And the third unspoken agreement is authenticity over trends. This is the big one and it's probably the hardest shift to navigate. When you're younger and still exploring, trends can be useful. They give you permission to try things. They provide a social and societal safety net in a way like, well, everyone's wearing this, so I can too. But at a certain point, you realize that following trends puts you on someone else's timeline. You're adopting and discarding aesthetics based on external cycles rather than your own internal evolution. But to be clear, the shift isn't about ignoring trends completely. It's about asking yourself, does this trend reveal something that I already wanted or am I just a lemming following it off the cliff blindly? I made an entire video about trends I have personally followed and adopted into my own personal style. even as someone who definitely does not make a habit of following trends [music] and I actually get very deep into the reasons and rationale behind those decisions. [music] So rather than trying to jam all this information into this little section, I'll link to the video up there. And for those who want to skip ahead to the payoff of that video, you can go to about 6 minutes and 40 seconds in to find what you're looking for. The personal style road map. All right, enough theory. Let's talk about how you actually navigate this evolution without throwing everything out and starting over or staying stuck where you are. I'm going to give you a four-step process. And you don't have to do all of these things at once. In fact, you shouldn't. But this is the sequence that works. And I am going to call it doing the deed. Diagnose, edit, [music] experiment, and document. Step one is to diagnose where you are. Before you change anything, you need to understand what phase of style evolution you are in. Are you in the early exploration phase where you're [music] still trying lots of different things, figuring out what resonates? Are you in the major transition phase? Something big changed in your life and your wardrobe hasn't quite caught up yet. Or are you in the refinement phase? You mostly know what works. You're just optimizing and editing. The actions you take will be completely different depending on where you are. If you're in early exploration, you should be experimenting widely, thrifting, trying different price points, testing silhouettes and styles. The goal here is data collection, if you want to think of it that way. If you're in the major transition phase, you need to be more strategic. Identify the gaps between your current wardrobe and your current life. Career change, move cities, body changes, whatever applies. If you're in refinement, you're not adding much. You're editing what doesn't necessarily serve you and upgrading key pieces to higher quality versions. And I'll tell you that most guys get stuck because they're taking the wrong actions for the wrong phase. [music] They might be taking refinement actions when they should be exploring or exploring when they should be refining. [music] Step two is to conduct an honest edit. Okay, this is where we actually look at your closet and start to be strategic about what's holding you back. So, grab a notebook or open your notes app. Go through your closet and put each piece into one of these [music] categories. Category A is the still feels like me category. These pieces stay. Don't overthink it. If you wear it confidently and regularly, it's earned its [music] place. Category B is the doesn't feel like me anymore, but I can't really articulate why. These are your evolution clues. Don't throw them out yet. Instead, write down what feels off. Is it the fit? Is it the color? The formality level? The associations you have with it? The lifestyle it implies. This category is going to teach you the most about where you're heading. Category C is the I'm keeping this because I should or because it was expensive category. These things are the hardest to let go of, but they're also the most important to let go of. That sport coat you spend $800 on, but haven't worn [music] in 5 to 10 years, it's not serving you. It's just taking up space in your closet and making you feel guilty every time you see it. I've been there. I know what it feels like. These black fleece jackets, they were expensive. I love them. Not my style anymore and can't tell you the last time I wore them. This All Saints motorcycle jacket, it was a gift, an expensive gift from Robin, so there's some sentimentality to it. But I don't ride a motorcycle anymore. And could you really see me in this today? Here's the key. You don't have to throw everything from category B and C away immediately. Box them up, store them for a few months. If you don't miss them or reach for them, that's your answer. All right, step three is where we get into some strategic experimentation. Now that you've created some closet space, this is the point where most guys make a mistake. They either buy nothing because they're afraid of making the wrong choice, or they buy too much to try to fill the gaps as quickly as possible. What you need to know about these two approaches is that both are wrong. Instead, what you want to do is identify one area where you want to experiment, just one. Maybe it's [music] a new silhouette, wider pants when you've always worn slim. Maybe a new texture, introducing more rugged fabrics when you've been doing [music] sleek and refined. Maybe it's a new color palette, earth tones, when you've been doing navy and gray. Or maybe a new formality level, dressing up or dressing down from your norm. Here is the specific approach for this kind [music] of experimentation. First, find one affordable example of this new direction. Thrift it, buy it on sale, whatever. The goal here is lowrisk experimentation. [music] Next, wear it three different ways with pieces you already own and feel confident in. This will force integration rather than a feeling of costume [music] wearing. And finally, document how you feel each time. I'm not talking about how you look, but rather how you feel. Confident, uncomfortable, like you're trying too hard, like you've discovered [music] something. And after that, if it feels right, invest in a higher quality version. If it doesn't feel right, well, you've learned something for $30 instead of 300. The key is to give yourself permission to fail. Every experiment that doesn't work still gives you valuable information about who you are and where your style is going. And the last step of the road map, step four, is to document your evolution. Now, this one sounds optional, but it is actually [music] critical. Take photos of the outfits you feel good in. Not for Instagram necessarily, for yourself. I literally do this for every single outfit video we make. When I'm putting looks together, I always take a reference [music] photo for each look. Then I add them to the video projects research and notes page, not only to help me visualize the flow of the outfits within the video, but also for my own personal reference. It's kind of like a less polished version of the style guide that we have on the Heespoke Style website, which is a tool that I created specifically for you to be able to find inspiration for different seasons or occasions. But to be honest, I use the style guide myself all the time. So, I've got these project pages for our videos. I've got the style guide that is sort of my own curated best outfit repository. But for you, all you need to do is to create a simple folder on your phone or a private Pinterest board. And what you're going to do is to use those things to capture what you feel is working for you. Now, do this for 3 months and then look back. And you know what? You'll start to see patterns like colors you gravitate toward, silhouettes that keep showing up, pieces you reach for constantly. Combinations that make you feel most like yourself. This becomes your road map, not some guide written by someone else. These are your actual preferences revealed through your real behavior. And here's the beautiful part about this. When you look at these photos a year from now, you'll see how you've evolved again. So documenting your style isn't about capturing perfection or doing it for the gram. that make me sound old. It's about honoring the journey that you are on. This is where I am today. Not where I was 5 years ago. Definitely not where I'll be 5 years from now. And that's not a problem to solve. That's kind of the entire point. Your style evolution isn't a sign that you got it wrong before. It's a sign that you're paying attention now, that you're growing, that you're staying honest with yourself instead of performing some static version of who you think you're supposed to be or who you think other people want you to be. The guys who get this right aren't the ones who never change. They're the ones who change intentionally. the ones who stay curious, the ones who give themselves permission to outgrow things that once felt perfect. So, when it comes to personal style, you never really arrive. Your style isn't broken when it changes. It's actually working exactly the way it should. It's a journey, and the question is, are you going to resist it or are you going to work with it? Thanks for watching and stay tailored.