My relationship with watches is surprisingly complicated. This makes me feel a bit uneasy because watches can be so redundant in a lot of ways. Why am I so conflicted about something so seemingly trivial? That’s a big part of the allure though, that these complicated things perform such a simple function. Even though my phone has the time I’m enamored by this machine that I wear on my body. What a curiosity that is.

As part of my journey into watches I’ve discovered that the watch world can be a very strange place. I think most watch people would admit this. It’s not bad necessarily, but it's also not as enjoyable as I would want it to be. Maybe the problem is me? The minute people start talking about watch reference numbers is the moment I start to lose interest. No details please. Though, I do actually care about details maybe just not all of the details. Do I care about the Apollo astronauts wearing it during the moon landing? Absolutely. Real historical significance matters. Other more brand specific details matter less. That's not to say I don't care about movements and how or where things are made. All of that is a factor, but I don't dig in too deeply. This is just how I do it and maybe I am wrong.

It’s not bad to be really into the details of things that interest you — I just think with watches it can be different sometimes. Watches have such a close association with a projection of wealth or status the hobby can attract the loathsome types which Instagram insists on serving you 24/7 in the discover page. It’s hard to look at that stuff and still stay in the game. Though there's a lot to like about watches so I try not to throw out the baby with the bathwater.

Watches are cool little machines that are easy to love. There’s also a lot of different types of watch people and ways to appreciate even the simplest and inexpensive timepieces. Most watch stories I read depend on a news hook or some sort of organizing idea (like materials or features). They don’t seem all that targeted in terms of recommending things to people with a shared point of view. That’s what I was hoping to do here. Regardless of why you like watches there are some great things out there. Here are 5 of my favorites.

( I don’t get a kickback for recommending anything in this story. No one paid me to do this and this newsletter is 100% subscriber supported.)

IWC Portugieser Automatic 40

It's shocking how much I love IWC as a product and as a brand. It really just aligns perfectly with my taste. My first real watch was an IWC and over the years I've continued to find ways to justify buying them. Somehow I've amassed a borderline absurd group of IWCs from the Pilot family because those designs really fit my eye. My first IWC-love however is the Portuguese collection (which is now officially called Portugieser). Somehow in 2010 I was invited to Portugal with IWC for a sailing trip around the launch of the Portuguese Yacht Club Chrono. It was in Portugal that I first met respected watch journalists Jack Forster and Jason Heaton who are both part of Hodinkee now. I definitely felt like the odd man out of an all-star group. That trip is where my appreciation of the Portuguese collection really took off.

Still all of these years later the Portugieser is one of my favorite families and the premier IWC collection (if you ask me). Last year the IWC Portugieser Automatic 40 was introduced. It's thinner than many previous Portugieser and stands out for the simplicity of the dial. This made me start to do some calculations in my head about what I could sell to get one. It's just a great watch that isn't too sporty or too far into the dress zone. It's a winner and you could own it forever.

Tudor Black Bay Chrono

When the Black Bay Chrono launched it was easy to understand that this was going to be a huge hit for Tudor. While we may all love the ceramic Daytona our chances of allocation are slim. I've always found Tudor to be a bit more approachable than its older brother. My first exposure to Tudor was when the brand was on hiatus from North America and I would see it in Asia. Mark McNairy wore a Tudor and it was one of those if you know you know type things before IYKYK was a thing people tried to say un-ironically.

I saw this Black Bay Chrono at a preview this spring and it's great. I would have felt ok to buy one sight unseen, but holding it in person confirmed it is awesome. I own two Black Bays (navy and black) and they are probably the watches I wear most often. This Black Bay Chrono is probably the closest I have come recently to buying something new. There's a lot to love here.

Hamilton Khaki Field Watch

My first mechanical watch was a vintage Hamilton Khaki. This is a great place to start (and end) a watch collection if you just want something solid and classic. Often I receive DMs from people looking to buy a watch as a gift. When the budget is sub-$1000 this and Seiko are the two I recommend most.

Even the most committed watch people can't help but to appreciate these watches. I've included these watches before and you might have seen me recommend the Khaki previously. That's just because it's perfect for a lot of people and fits almost everyone's budget. If you do end up buying one used on eBay or wherever, you will likely want to have it serviced or things could stop working. That expense and process tends to push me into buying new over vintage. It is hard to resist the U.S. military issue watches though.

Drive De Cartier

One of the reasons I'm a bad watch collector is my love to deviate from the most conventionally loved timepieces. So while I love the classic Cartier Tank, I wouldn't actually buy one. (Although I am intrigued by the SolarBeat.) I would buy a Reverso instead. A JLC is not as common or as easily recognizable. Does this matter? Not to anyone but me. I only point this out because here I will overlook the Tank to consider the Drive De Cartier.

I actually went to the Cartier factory to see how these watches are made and I have loved them ever since. The shape of this design really grabs me — being almost round with square accents. It's unique and is such a wonderful contrast to the roman numerals on the dial. Often I don't think I dress up enough to pull off Roman numerals, but this just works. The rose gold and brown leather is the perfect combination of colors and textures. The precious materials here don't make this inexpensive, but we can all dream a little bit.

Seiko

The brand that's easiest for me to recommend is not surprisingly Seiko. It's really a great option when it comes to value for money. As a brand, Seiko is a perfect case-study in all of the reasons to love watches — the high and the low. The history, innovation, and fun association watches can have with sport. I love what the brand says about the wearer too. Seiko screams practicality, sensibility, an appreciation for quality, and of course value consciousness. I'm always conscious about what the watch I am wearing says to the world — good and bad. I would never want to own a crazy expensive watch and for the people I work with or for my clients to see me as overpaid. The good news is I can't even swing a super expensive watch so that problem is working it self out naturally.

A Seiko looks good, is made well and isn't expensive. You don't have to worry about it or insure it. There are so many positives which must explain why a lot of hardcore watch people love and respect the brand.

The one issue with Seiko is the breadth of the collection. Everything is not a home-run design wise and I generally try and stick to the Prospex collection. I just love the shapes and styling of the Seiko dive watches. If you go to Japan you can also find some special things that don't make their way over to the U.S. Here's one I bought on my last trip there.

Thinking of buying a pre-owned watch? If my friends ask me this question there’s a few places I would feel comfortable recommending. Disclaimer, no one person is going to have the answer for what you should buy and from whom. That said, these are the places I would recommend to a friend.

A Continuous Lean.

5 Good Watches