Out of Office: How We Spent Our Winter Break, Part I – feat. Tudor, IWC, & Rolex

For this edition of Out of Office, the team writes about what they wore when they were literally on vacation over the course of the recent winter holiday season. The idea was simple: pick a watch, wear it over the break, and chronicle your experience with it. What kinds of winter adventures did our editors get up to? Would any of them even leave the house? Find out below, and come back later this week for part II.

Zach Weiss

This holiday season, I purposefully spent a decent amount of my time on my couch, chilling. Decompressing from a very intense but exciting year here at Worn & Wound. I won’t regale you with what watches I wore as I caught up on Andor (excellent, btw) and a slew of mediocre horror movies. Rather, I’ll talk about the one watch I took on a short trip to Montreal the week before Christmas.

One of the things I enjoy about traveling, as demented as this might sound, is the challenge of only having one watch. Yes, these days, I don’t even take a watch roll. Whatever watch I leave my apartment with is the watch I’ll wear for the duration. Why? Well, it’s a good opportunity to “bond” with a watch. Forge some memories around a hopefully fun trip that can be triggered by looking at the watch as some later date. It also makes me think about which watch from my collection is best suited for the trip.

ok, this photo was taken in London last year, but it is my Black Bay Pro

Admittedly, I’m not the most adventurous person, so my trips tend to involve walking a lot, sightseeing, a mix of casual and upscale dining, some/many drinks, taking photos, a little shopping, museums, etc… That said, I like my watch to be more prepared than I. This has led my defacto traveling watch to be the Tudor Black Bay Pro. In fact, it’s the main reason I got it. With the closed borders of the pandemic peeling away entirely over the last year or so, the idea of travel became a reality again, and I wanted a watch that could handle anything that might come up.

Getting quickly tossed in a bag or basket at the airport is no concern for the rugged steel build. The dial is legible day and night thanks to molded lume blocks that glow so damn well. It’s a chronometer with 72-hours of power reserve, so accuracy is guaranteed. It’s water resistant to 200m, so getting caught in the snow and rain doesn’t matter at all. Of course, it can track multiple time zones, though that didn’t come up on this trip. But most importantly, and I’m not kidding, is the bracelet with T-fit clasp that can be easily adjusted through the day. 

On a light hike up Mount Royal after a large meal. The T-fit came in handy

My trip to Montreal was very much a “let’s just get out of town for a few days” type of jaunt. Neither I nor my girlfriend had been there, so a few days of exploring sounded perfect. And by exploring, I mean a mix of walking and eating. Yes, this trip revolved around meals, and Montreal did not disappoint. Poutine isn’t just a thing, it’s a way of life, apparently, and one that I found very attractive. 

We had poutine twice, first at a nice little bistro by our hotel which featured some slow-cooked lamb, and then at a Montreal institution, Schwartz’s Deli. About a 40-minute walk from our hotel, the mix of smoked meat perfected over decades with diner-style brown gravy, chunky cheese curds, and unfussy fries, paired with black cherry sodas, and a matching smoked meat sandwich was worth making the whole trip over again. 

Schwartz’s doesn’t mess around

This calorie-bomb breakfast/lunch combination gave us the energy we needed to climb to the top of a snow-covered Mount Royal park. Not much of a test for the Black Bay Pro, but dare I say the watch felt equally at home in a densely packed though humble in style deli, sharing a table with strangers as we consumed too much meat, as on a steady, snowy incline in sub-freezing weather. Of course, this is one of the many times the T-fit came in handy. Salty smoked meat met a wrist swelling under a down coat under moderate strain. Millimeters of comfort were added, and I knew my choice for wrist accompaniment was well-considered.

I won’t bore you with the rest of the trip as it played out in a similar fashion. Montreal bagels were tried, an exceptional and odd meal was had at Pied de Cochon that included “duck in a can”. Many miles were walked including in the Mile End area, which led us to a great little menswear shop called Clark Street Mercantile which had a stellar vintage Nivada Artic on display. Many cocktails were sipped, as was onion soup. Great Basquiat and Diane Arbus exhibits were visited to keep us out of the worst of the weather. A blizzard was flown through. 

an unexpected and gorgeous Nivada

All the while, the Tudor Black Bay Pro maintained a steady beat, keeping us on time for our reservations and inevitably-delayed flights. Wrist fluctuations were no trouble, thankfully. Needless to say, I look forward to my next trip, and will likely select the same watch as my horological companion.

Duck in a Can – better than it looks
excellent cocktails with a whale spine in the background
The scene from our table at Schwartz’s – shot by Sofya Perelman

Zach Kazan

Winter break for me was defined by pure and total relaxation. After a year of frequent travel, the last thing I wanted to do was jet off somewhere, away from the comforts of home that I had perhaps taken for granted during this first full year of “normal” activity post pandemic. I had nearly two weeks off, completely to myself, and I was thrilled to have a calendar that was entirely empty. I’ve learned that for me, being able to enjoy your life with a bare minimum of commitments is the ultimate luxury, and I took full advantage during my time away from work. 

When I shut my laptop for the final time in 2022, I was wearing my IWC Pilot’s Watch Chronograph 41 in Ceratanium. No surprise here, as it’s the watch I’ve been wearing with the most frequency since I took delivery midway through 2022. Now, I can’t sit here and lie to you: there were occasions over my holiday break where I switched watches, and put something else on for a brief period of time. I knew I’d eventually be writing this Out of Office segment and that the whole idea was to wear one watch for the entirety of winter break, but reader, I failed. What can I say? If watch collecting is in fact the manifestation of some type of minor mental instability, this is how it takes shape for me. Given the option, I can’t not switch it up at least every four or five days. I know I’m not alone, so I beg for your forgiveness and understanding. 

Photo by Cassie Zhang

That said, I was successful in wearing my IWC on the rare occasion that I decided to venture out into the world during my break. Mostly I hung out at home, here in Concord, NH, where I made a wonderful chili in my slow cooker, cleaned the apartment from top to bottom (an underrated and therapeutic activity, particularly while catching up on favorite podcasts) and watched a lot of movies. But this was my watch of choice for connecting with old friends over the holiday as well, which made for some interesting conversations. 

During my day to day life, I’m very much of the belief that the world around you simply doesn’t care about the watch you’re wearing. My friends and family that I see all the time know what I do for a living, and unless they are similarly interested in watches, what I’m wearing just doesn’t come up. Just like I’m not likely to start a conversation with a buddy of mine about his sneakers (because I’m not a sneakerhead), I don’t get asked a lot of questions about my watches, because most of my close friends are not watch obsessives. I’m grateful for this – it keeps my life well rounded. 

But the holiday season is different. It’s a time of gatherings and reconnections with friends and family that I might not see on a regular basis, and a good chunk of my holiday break was spent catching up with people who have been in my life for 30-plus years that I see maybe once every 6 months or so, or even less. Naturally, part of that catching up involves checking in on the career, and I’m always excited to explain the last few years of my life and how I’ve wound up doing what it is that I do. It’s not exactly how my high school guidance counselor laid it all out for me, after all. 

Photo by Cassie Zhang

So once I explain that I write about watches and that I’m deep into the watch world on a personal level as well, the question is inevitable: What are you wearing right now? The words fall out of my mouth in a way that I imagine is the opposite of graceful, and the conversation grinds to something of a halt.  

“This is the IWC Pilot’s Chronograph in Ceratanium”

“Yeah, IWC is a Swiss brand that’s been around for a long time – they’re known for their pilot’s watches!” 

“No, no, I’m not taking flying lessons…” 

“Well it’s a special titanium alloy that IWC makes that takes on ceramic-like qualities when heated in a kiln – the dark gray color is natural, it’s not a coating! And you can’t scratch it, really!” 

“Look at it in terms of cost per wear, though. If I own this watch for the rest of my life and wear it all the time it seems like a pretty good value to me!” 

Photo by Cassie Zhang

Some watches, more than others, require an explanation. I love my Ceratanium IWC, but I have to admit, wearing a Timex would have been more easily understood. Choosing something a little bit obscure might mean flying your watch nerd flag for longer than you might want to when you’ve only got a few hours with people you see once a year. 

Of course, these people who have known me for most of my life understand all too well how nerdy I can get about a whole range of topics, so the silliness of these conversations might not even register to them. And then there’s the possibility that they’re genuinely interested, and through an awkward interaction I’ve potentially intrigued someone enough to visit a site like Worn & Wound to continue learning about all kinds of watchmaking minutia. Mostly, though, I came away from my winter break glad to have reconnected with friends who mean a lot to me, even if they’re reminded of what a weirdo I am. 

Thomas Calara

The past few years have been a quiet holiday season for myself. I was living in Southern California and thoroughly enjoying the sunny and 75 degree weather in the middle of December, with my entire family living back east. But since last July, I’ve returned to my home state. The Garden State. New Jersey is where I’ve spent most of my holidays during my 34 years on this Earth, running around from house to house, going through the same routine: Greet, Eat, Chill, Repeat. This year was my first holiday season back, and I must say, I really did miss the colder weather, thicker layers, and the excitement surrounding the holidays.


This past Christmas was split between hanging out with my family in central Jersey for Christmas Eve and then closing out the holiday weekend at the ‘Farm’ with the in-laws. It was just as I remembered. Loud jovial voices that only got louder. Uncontrollable laughter. And a smorgasbord of Filipino cuisines, Italian classics, unnecessary amounts of desserts, and other traditional dishes served during this time of year. As I said – Greet, Eat, Chill, Repeat. 

As for the watch, I was only wearing one, and that was old-faithful; the Rolex Explorer 14270. This was the watch I had on my person during my first child’s birth in March of 2022, and really has been the only watch that I’ve wanted to wear so that proper memories are built into it. It was the watch on my wrist when I made the move back east, hauling all my personal belongings that could fit into a carry-on bag clutched in one hand, and carrying a 5 month old in the other. It was the watch I had on when he spoke his first word and was on the wrist when he made his first crawl a couple of weeks ago. Naturally, the Explorer was on the wrist for his first Christmas. 

Not quite the Out Of Office you’d expect, right? There was no canyon to trek or a beach break to surf. Just good times, with great people. As for the Explorer, was it up to the task to be on my wrist as I built sky-high gingerbread houses, navigated the landscape of holiday sustenance, and a few bouts of walking around the farm? Absolutely. The only hazard here was that the bracelet on the Explorer was a bit snug on the wrist to begin with, so you can imagine the “Crown” imprint that got left behind after a weekend of gluttony. If only the 14270 had a T-fit clasp…sigh. 

Now, I know this isn’t a “Watch Resolutions” post but this is where I’m going to leave this. I’m going to try (and have started already) to thin out the collection. I’m also going to lean into wearing the watches that I own more often, and for longer stretches of time. Lastly, I’m going to finally take the plunge and buy my first GMT watch this year, and hopefully get to experiment more in the process.

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