(Help support this site! If you buy stuff through my links, your clicks and purchases earn me a commission from many of the retailers I feature, and it helps me sustain this site—as well as my menswear habit ;-)  Thanks!)

Three watches for most occasions: the daily, the weekend, and the special occasion. That’s the idea behind Crown & Caliber’s series of YouTube interviews (scope out the ones with Sid & Ann Mashburn; his approach to watches in relation to his wardrobe really resonated with me). If you become enamored of watches, it’s hard not to begin collecting them. They’re beautiful; they often are tied to a story, either personal or historical; there is a rich diversity of styles and designs you can choose from to express your own style. Too often, though, they begin to fill up your drawer. So the question is: if you had to just narrow it down to three, which would you choose?

I posed that question to my dad. I’ve worn a watch every day since I was at least in elementary school, and it’s because of him. (I’d also say his example of dressing well rubbed off on me, too.) He’s worked as a marketing professional in the publishing industry for many years, and has been buying and wearing fine watches as long as I can remember. He grew up in Eastern Nebraska, and as a skinny kid did everything he could to toughen up (ice baths, overnight solo hiking trips in the winter, Boy Scouts adventures in the wilderness) to defend against the bullies at school. If you saw him as an adult, you’d never know it from his tall stature and muscular build. But what he’s known for—by everyone who’s ever met him—is being a kind, generous man who’s genuine and without guile. He’s my hero in many ways, and here are his three choices for a watch capsule collection.

During a recent visit, he pulled them out and we talked about why he chose the ones he did. As a bonus, he told me what his choice would be if he could only choose one. I enjoyed our conversation, particularly because he hasn’t just been buying watches recently (one of his selections is 40 years old), so his style is mature, not just driven by the newest shiny thing.

1. The Everyday Watch

Tudor 1926, 41mm, Reference M91650-0005 (here’s a saved eBay search for this Tudor watch; I like eBay for reasons listed here)

Why this watch?

“I like the Jubilee-style bracelet. The clasp is silky, and the dial is reminiscent of how my dad used to hand-write his numerals. The waffle texture adds a touch of class.”

Why is it your everyday?

“I work in the marketing office, so it’s classy and elegant but not pretentious. It has the Rolex quality, but it’s subtle so I get the personal satisfaction of knowing it has the quality. The bonus is, those who know, know. I feel neither underdressed nor overdressed with it.”

(Editor: I should note that my dad has big, manly wrists, so 41mm fits really well on him. The 1926 is a watch that doesn’t get a lot of attention, but the more I spent some time with it, the more I appreciated it. I would agree, it’s a beautiful watch that has an elegant overall profile, shape and design, while bringing it down to earth with the Arabic numerals and textured dial).

2. The weekend watch

Seiko Diver 6309, 150m, automatic. He calls it his “Bulky Sports Watch” (eBay link for this Seiko here; more about this watch at Fratello)

What do you like about this watch?

“I like this because it’s instantly legible from any angle. It has a smooth second hand, and both the day and date are useful to me. The rubber dive strap on it is the perfect compliment to the rotating bezel.”

What’s the story behind the watch?”

“I saw it on sale at a significant discount in 1981 in an East Texas grocery store. I wanted to buy it on the spot, but I didn’t. But I came back a week later and it had dropped another 30% in price, and I bought it. I wanted a Submariner, but couldn’t afford one. I got this practical equivalent for $95. Sadly, when I sent it to Seiko for service a couple of years ago, they couldn’t source the gaskets to make it water resistant. But, for my weekend use, I don’t hesitate to wear it, which is something I wouldn’t be able to say about a Submariner. I love that it’s tough, so I wear it when I need to work on the lawn mower or plant a tree, that sort of thing.”

(Editor: My dad has had this watch since before I was born, and I’ve even worn it occasionally when I lived at home. Since getting into watches I’ve learned this watch has kind of a cult following. One thing that’s really odd about it is that it has no way to manually wind it; if it needs wound up you must physically shake it to move the rotor inside. Once again, my dad’s large wrists accommodate the watch on the rubber bracelet very nicely, much better than on me).

3. The special occasion watch

Longines Record, 40mm, COSC certified chronometer movement, reference L2.821.4.11.6 (saved eBay search for the Longines)

What do you love about this watch?

“It has the most elegant Roman numerals that I’ve seen. I love the navy hands and the display back. I took off the stock stainless bracelet, and put it on a leather deployant, which looks more formal and elegant to me. The stainless bracelet was beautiful, but I prefer the leather for how I wear this watch.

“Unlike the bulky sports watch and Tudor, it doesn’t have a screw-down crown, so I can stem wind it more easily.”

What’s the story behind the watch?

“I gave my best dress watch—a very thin and elegant Raymond Weil oval quartz watch with Roman numerals, which I had bought when I got a promotion years ago—to my best friend recently. So when I gave that away, I needed a replacement, and I absolutely loved this Longines the moment I saw it.

“If I had to pick a watch to meet a president or foreign head of state, this is the one.”

(Editor: I love this watch. Longines is an outstanding choice for someone who wants a nice Swiss watch without spending crazy amounts of money).

Bonus: The One Watch

Omega Seamaster Professional 300m, automatic, 41mm, reference 2531.80.00

Why do you love this watch?

“I bought the watch in spite of its association with James Bond (I don’t want anything to do with James Bond). I love the scalloped bezel and silky smooth bracelet. At that time, it was the nicest watch I’d ever owned. I bought one for my firstborn son when he graduated high school. A year later he returned the favor by finding me an absolutely amazing deal on one at a Steamboat Springs jewelry store, and I pounced. “For many years, I let my second born son (editor: yours truly) wear it whenever he wanted. Now that he has his own stable of watches, it’s back in my possession and I am enjoying it once again.

What makes it your choice as the ‘One Watch’?

“It’s versatile. It has rugged good looks; it’s suitable as a fancy dress watch and for casual wear, too. I could wear it to work, to church, to the pool, or the beach and it will be a perfect complement to any of those situations. I particularly like the faded blue bezel, which speaks to its years of happy memories, both my own and my son’s.”

(Thanks to my dad for showing me his watches and telling me about them. He also lent the ring and bracelet for the photos above, both of which have their own cool stories.)

(Help support this site! If you buy stuff through my links, your clicks and purchases earn me a commission from many of the retailers I feature, and it helps me sustain this site—as well as my menswear habit ;-)  Thanks!)

If you’re just getting into tailored menswear and want a single helpful guide to building a trend-proof wardrobe, buy my eBook. It’s only $5 and covers wardrobe essentials for any guy who wants to look cool, feel cool and make a good impression. Formatted for your phone or computer/iPad so it’s not annoying to read, and it’s full of pretty pictures, not just boring prose. Buy it here.