Why A Rolex Datejust Was My First Luxury Watch Purchase

If you've watched the channel for a while now, you know that I really love watches, especially nice watches. But it wasn't like the first watch that I ever owned or watches that I've had throughout my life have always been luxury watches. Getting into and appreciating watches, developing and refining my taste in watches is something that has been a very long journey. And you're going to find out how I eventually found myself walking into the Rolex boutique on Fifth Avenue in New York City with a pocketful of cash, ready to buy my first luxury watch, a Rolex Datejust. So the first watches I ever had as a kid were a Timex Ironman Triathlon. I love that watch. Don't know what ever happened to it, but I'm seriously considering searching on eBay to try and find one purely for sentimental reasons. Also, as a kid, I had a neon colored Swatch that had a rotating bezel. And then of course, there was the Gucci, obvious scare quotes there, that I bought on Canal Street, i.e. not a real Gucci watch, on a class trip to New York City when I was in high school. There was a period of time when I didn't really think about watches that much at all. I was in college, grad school, and I was just laser focused on that experience, practicing my saxophone, playing gigs, and watches kind of took a backseat to all of that. But then once I got settled, had a job, and finally started thinking more about improving how I dressed, building up my wardrobe, that's when I began scratching the surface of the watch hobby. Watches, in my mind, were a finishing touch to an outfit, and also, like clothing, a way to communicate something about yourself. My first foray into watches at that time was very modest. I didn't really know anything other than that I wanted a watch that I could wear with a lot of stuff, and had a timeless, no pun intended, really, look. And I also didn't really know where to look for watches, so the first one I actually got was from J.Crew, and it was the Timex T2N321 Circa 2010 for J.Crew. Came on a brown leather strap, and I also ordered a black strap for it from Amazon, as I recall. Very small and elegant stainless steel case, simple dial with a date window. I wore this watch all the time, and if you go back to the early years of HSS on the website, you'll see this watch in pretty much every single post. So that was kind of the watch that rekindled my interest, and shortly after that, I started getting the urge to have more options. The Timex was great, but I wanted something on a metal bracelet and in a gold tone, so I went to the mall and I bought a Citizen EcoDrive. And then eventually, I spent a little bit more and got a Uniformwares C40, which is a cool minimal watch with a day date. So you're probably wondering, like, how does someone go from a $600 Uniformwares watch to a new Rolex Datejust, which was actually my next watch after the Uniformwares? Because I'll admit, that is a huge leap to make. For me, it was a combination of two things. It was circumstance, and it was also, because I am who I am, the fact that watches really became a very strong interest. And when I get into something, I pursue it with passion, and if it becomes a goal, it's something that I try my hardest to achieve. So Rolex had become, in my mind, at that particular time, the pinnacle of arrival. Now, you could be cynical about their marketing and how they position themselves as the reason that that thought was in my mind, and maybe that's the case, and if so, good for them. But there's also a reason that Rolex is Rolex, and why people sometimes say, bow to the crown. Although they might not make the most beautiful movements in the world, there is no disputing that they are exceptional quality, and have an amazing history. But back to circumstance, Rolex is a luxury brand, and it's a luxury price point. So you've got to be in some sort of financial comfort zone to afford one. He Spoke Style had been doing very well, and that put me in a position to seriously consider this purchase. And although it might sound cliche, but marking that kind of milestone with something like a Rolex watch, really added to that sense of achievement and accomplishment that I felt. Something that I would have, and something that I could always look to, and remember the pride that I felt about that. Obviously, and again, because I am who I am, I didn't just run out the next day and buy a watch. I'd never spent that amount of money on anything all at once. So I dove into sort of an insane level of figuring out what the perfect Rolex was going to be for me. And that started with going to the boutique, and actually trying a few models on. Robin was living in New York at the time, so we were kind of back and forth every other weekend. So on one of the trips up there, I went to the Rolex boutique on Fifth Avenue, and also hit up Torno. The experience of actually putting these watches on my wrist for the first time was kind of transformative. I'd only been used to relatively inexpensive watches, and there is a very different feel on the wrist when it comes to a modern Rolex. It has a solidness and heft that for me was just really unexpected, and made a very big impression on me. It just felt like this is a high quality watch. Two questions I bet you have right now are, how and why did I settle on a Datejust? And why did I choose to purchase brand new instead of pre-owned? Although I briefly considered a Submariner, I settled on the Datejust for a few reasons. I wanted something that was classic. I wanted something that was versatile. And I wanted something that leaned more toward the dressy side of things, because that tends to be more of my default mode of dressing. So once I'd settled on the Datejust though, there was still a big decision I had to make between an Oyster bracelet or a Jubilee bracelet. Oyster would be more casual, and Jubilee would be a little more dressy. And once again, I leaned more dressy because it matched my style and seemed a little more special to me. And then size, 36 millimeter versus 41. I chose 36 because it was more classic and fit my wrist a lot better. Now new versus pre-owned. I wanted to buy new simply because I wanted the watch to be completely mine. I didn't want to have a story before me. I wanted to write its history myself. So as I tell it here in all of two minutes, it makes it sound like it was a pretty simple process that I went through and that it didn't take long at all to arrive at my final decision. But in reality, I agonized over this for a good nine months. I'm going to spend all this money. I better make sure that I've done all my research and that I am 100% confident that this is indeed the watch that I want to buy. I spent a lot of time reading articles. I spent a lot of time on the forums. I spent a lot of time on the Rolex website, playing with different configurations. Once I arrived at my decision, however, I went to the bank, made the trip to New York for the weekend. And before we left the apartment, and this sounds like completely ridiculous, but Robin had a colleague at the time who ran this Instagram account called Cash Cats, which was like photos of cats laying around in piles of money. So we actually took a picture of her cat Ringo for Cash Cats. See, I told you it was ridiculous. So the transaction in the boutique was kind of the most boring part of the whole affair. And the only thing that kind of sucked about it was that instead of leaving with the watch on my wrist, I actually had it mailed to me in Maryland. So it came like a few days later. So that's the story. Now let's take a closer look at this watch and all of its details with some good old-fashioned watch porn. So here it is, my Rolex Datejust reference 116234. It is a 36 millimeter case in oyster steel and white gold. It's got a screw-down case back, which you can't see through, and a screw-down crown. Jubilee bracelet, giving it a dressier look. Also contributing to that dressier feel, it has a fluted bezel, which looks amazing as it catches the light. I mentioned that I wanted something extremely classic, so I went with a silver dial and stick pin hour markers. Hour, minute, and running seconds hands. It does hack, which if you are really anal about setting the time accurately is an awesome feature. It is an automatic movement, and of course the real signature feature is the cyclops, which magnifies the date window. This watch looks great on the wrist, and I feel like 36 millimeters is a perfect fit for my six and a half inch wrist. It's incredibly comfortable to wear. It still is one of my favorite watches. Gets a lot of wrist time, and it will always have a very special meaning to me. As I went through the process of buying this watch, I learned a lot. And if you find yourself in a similar position as I was, really wanting a Rolex to be your first luxury watch purchase, I put together a video link right over there that goes even deeper and gives you some really important questions that you should be asking yourself to see if this is the right choice for you.