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The Story of My Rolex Datejust

January 7th, 2021

Why Did I Buy A Rolex Datejust?

If you’ve been a fan of HSS for a while now, you know that I really love watches-especially nice watches. But it wasn’t like the first watch I ever owned or watches that I’ve had throughout my life have always been luxury watches.

Getting into and appreciating watches and 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 pocket full of cash ready to buy my first luxury watch–a Rolex Datejust.

Where did this start?

One of the first watches I ever had as a kid was a Timex Ironman Triathlon. I loved that watch. Don’t know what happened to it, but I’m seriously considering searching eBay to try and find one purely for sentimental reasons. Also, as a kid, I had a neon-colored Swatch with a rotating bezel. And then, of course, the knock-off “Gucci” watch I bought on Canal Street-on a high-school class trip to New York City.

There was a period of time, though, where I didn’t really think about watches. I was in college, grad school, and was laser focused on that experience, practicing my saxophone and playing gigs. Watches kind of took a back seat.

But once I got settled, had a job, and started thinking more about improving how I dressed, I began scratching the surface of the watch hobby. Watches, in my mind, were a finishing touch to an outfit. Like clothing, they were a way to communicate something about yourself.

My Early Watch Days

My early foray into watches was very modest. I didn’t know much other than wanting a watch with a timeless (no pun intended) look I could wear with a variety of outfits. I also didn’t really know where to look for one other than major mall retailers.

The first was the Timex T2N321 for J.Crew (circa 2010) with a brown leather strap. I also ordered a black strap for it on Amazon. It had small and elegant stainless steel case and a simple dial with a date window. I wore this watch all the time. If you go back to the early years of HSS, you’ll see this watch in pretty much every post.

That was the watch that rekindled my interest. Shortly after, I got 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 bought a Citizen Eco Drive. Later, I spent a little more on a Uniform Wares C40, which is a cool minimal watch with a day-date complication. But, the watch after that was the Rolex Datejust.

How Did I Go From Uniform Wares to Rolex?

I’ll admit going directly from a $600 Uniform Wares watch to a new Rolex Datejust is a huge leap.

For me, though, it was a combination of two things. It was circumstance, yes. And it was also the fact watches became a very strong interest. When I get into something, because I am who I am, I pursue it with passion. If it becomes a goal, it’s something I try my hardest to achieve.

Rolex had become, in my mind at that particular time, the pinnacle of arrival. Now, you could be cynical and say their marketing and how they position themselves as a luxury brand is the reason for that.  Maybe that’s true. If so, good for them. But there’s also a reason that Rolex is Rolex. Although they might not make the most beautiful movements in the world, there is no disputing they are exceptional quality and have an amazing history.


But, back to circumstance. Rolex is a luxury brand and commands a luxury price point. He Spoke Style had been doing very well, and years of hard work put me in a position to seriously consider this purchase. Although it might sound cliché, marking such a milestone with something like a Rolex watch added to the sense of achievement. It’s something I would have, something I could always look to and remember the pride I felt.

Obviously, and again, because I am who I am, I didn’t just run out the next day and buy one. 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 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 back and forth every other weekend. On one of the trips up there, I went to the Rolex boutique on Fifth Avenue and also hit up Tourneau. The experience of actually putting these watches on my wrist for the first time was kind of transformative.

Before, I’d only experienced relatively inexpensive watches, and a modern Rolex has a very different feel on the wrist. It has a solidness and heft that, for me, was just really unexpected and made a deep impression on me. It just felt like “this is a high quality watch.”

Why Did I Purchase A Brand New Rolex Datejust?

Although I briefly considered a Submariner, I settled on the Rolex Datejust for a few reasons. I wanted something classic. I wanted something versatile. And, I wanted something toward the dressy side of things because that’s more of my default style.

Once I’d settled on the Datejust though, there was still a big decision to make between an Oyster or Jubilee bracelet. Oyster would be more casual and Jubilee a little more dressy. I leaned dressy again because it fit my style and seemed a little more special. As for sizing, I chose 36mm over the 41mm because it was more classically-sized and fit my wrist better.


Now new vs. pre-owned. I wanted to buy new simply because I wanted the watch to be completely mine. I didn’t want it to have a story before me-I wanted to write its history myself.

Writing this now it makes it sound like a pretty simple process. But in reality, I agonized over this for a good nine months. If I’m going to make this purchase, I’d better do my research and make sure I am 100% confident this is the watch I want to buy. I spent a lot of time reading articles, browsing forums, and playing with different configurations on the Rolex website.

Once I arrived at my decision, I went to the bank and then made the trip to New York for the weekend. And before we left the apartment-this sounds completely ridiculous now- we took some photos. Robin had a colleague at the time who ran an Instagram account called Cash Cats, which features photos of cats laying around in piles of money. So, we actually took a picture of her cat, Ringo, with the cash I was going to use to buy the watch.

So, in a way, the transaction in the boutique was the most boring part of the whole affair. And the other thing that sucked was I wasn’t able to leave the shop with the watch on my wrist. I had it mailed to me in Maryland, so it came a few days later.

The Watch Today

This watch looks great on the wrist, and I feel like 36mm is a perfect fit for my 6.5-inch wrist. It’s incredibly comfortable to wear. It still is one of my favorite watches, gets a lot of wrist time, and will always have a very special meaning to me. If you’re looking to buy your first Rolex, definitely check out this article.


Do you have a “first luxury watch” story? Share it below in the comments!

Thanks for reading.

Stylishly Yours,

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal,, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

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Videography by Rob McIver

Video Editing by Ian Johnston


I live in Baltimore and about eight years ago, I got in my car and headed south to Washington, DC. I knew why I was going, but wasn’t exactly sure how it was going to go.  I didn't realize until many years later just how significant this trip would be.

I was headed down to DC because a custom clothing company from New York I had read about and heard really great things about was setting up shop in DC and was offering a nice discount for first-time DC clients. This was during the very beginning of He Spoke Style and at a time when I really started to get serious about developing my wardrobe and investing in it. It seemed like a good trip to make.