Finding The Right Watch For Your Wardrobe

June 26, 2018

Finding the Right Watch for Your Wardrobe

Even if they’re both into style, the online communities for men’s clothing and fine horology exist on different islands. The guys who are into suits and offbeat Japanese workwear are often not that up on watches. And the guys who are into horology are perhaps not always that interested in clothes.

So we interviewed four stylish men who have an active interest in watches to see how they match the different components of their wardrobe. Which watches do they wear with suits, which do they wear with business casual, and which do they wear with weekend gear? And what are some affordable alternatives with a similar look? The idea was to cover a broad range of styles so that readers can get a sense of what might work for them.

Each of our four interviewees represents a slightly different style. Stephen Pulvirent from Hodinkee is pictured below in a sport coat, but off camera, he’s often in contemporary casualwear with a more minimalist flavor. Gary Tok, author of Master Shoemakers, jumps between tailored clothing and classic casualwear. Takahiro Osaki is mostly in Italian suits and sport coats. And Kento Tsujimoto of The Real McCoy lives in repro-style workwear. Here are the watches they said they wear, and how they think certain watch details matter. (Spoiler: vintage Rolexes were a crowd favorite, and if you have the scratch, Rolex Explorers in particular — a watch Ben Clymer has also endorsed).


Stephen Pulvirent, Managing Editor at Hodinkee

My wardrobe has become a lot more casual over the years. There was a time when I think a lot of guys, including me, were into suits and intense pattern matching. But nowadays, I’m often in something as simple as a t-shirt and some jeans, maybe a chunky lambswool sweater. I also have a grey suede asymmetrical zip jacket from Stoffa that I love. If I have to go to an industry event or meeting, however, I’ll put on a sports coat and some trousers. The number of times I have to wear a suit nowadays is pretty limited, although it happens.

So my wardrobe is fairly minimalistic and simple, with lots of blues, greys, and other neutral colors. For this, I find vintage Rolexes work really well. They’re not too dressy, but they can also be worn in different ways – from casualwear to tailored clothing. And they’re relatively understated. 

For about three years, I mostly wore a Pepsi dial GMT (ref. 1675), but then I sold it to fund another purchase. I picked up an early gilt dial Rolex Explorer (ref. 1013). I was a little hesitant at first about selling my GMT, but I couldn’t be happier with my decision in the end. The Explorer is sporty, but it measures 36mm and neatly slides under a shirt cuff. And unlike the GMT, which I think looks better on a bracelet, I think the Explorer can be worn with almost anything – a bracelet, Barenia leather strap, or rougher suede strap. It just gives the watch that much more versatility.

The other watch I keep coming back to is a Universal Geneve Polerouter, which was my first vintage watch purchase. I have one with the asymmetrical date window. It has a dressier 1960s feel, but I wear it with sweaters and jeans, sometimes a polo shirt. It was intended to be a sports watch back in the day, so I think it has a bit of that sensibility.

There are times, however, when I like to wear something that’s genuinely dressy. I think if you’re getting really dressed up for a nice event, putting on a slim, precious metal watch can feel like the finishing touch to a more formal outfit. I inherited a small, yellow gold Longines from my grandfather, which I wear to these sorts of events.  I also have a Nomos Tangente 38. I only wear these about four or five times a year, but they always feel special when I do.

(photos via Stephen and Hodinkee)


Gary Tok, author of Master Shoemakers

I think of watches in terms of three categories: formal, semi-formal, and casual.

Formal watches are what I would wear with a tuxedo or very conservative business outfit (e.g. dark worsted suit, white shirt, and conservative tie). For these things, I think the watch should be a smaller, more discrete design – smaller than 40mm and be thin enough to fit under a shirt cuff – then have a round, rectangular, or Tourneau shaped case in steel or gold (yellow, rose, or white). It should either have a time-only function or, if you want to be fancy, have things such as a perpetual calendar, annual calendar, or minute repeater. But no GMT or chronographs. It should also be on a leather strap, preferably in black or navy.

The reason is because you want something very discrete and understated in these environments. I personally have two Patek Gondolos (ref. 5111 and 5124) because I really like how rectangular cases work with a conservative suit. But I also think something such as a Nomos would work in these situations. They’re a German brand with very simple, minimalistic designs. And as far as watches go, they’re a bit more on the affordable side. 

Next are semi-formal watches, which are what I wear with sport coats or smart/ business casual. These can be either classic dress watches or sports watches under 42mm. You can wear these on a leather strap or metal bracelet. Since you can be a bit more adventurous here, a chronograph is fine. Although I still think PVD or any other metal color besides steel or gold shouldn’t be worn with a tailored jacket.

These are the watches I wear most because, depending on what you get, they can be pretty versatile. I mostly wear a vintage Rolex Submariner (ref. 5513) and Pepsi GMT (ref. 16710) these days. The GMT is really useful because I travel a lot and the watch allows me to keep track of time in different time zones. I also think they can be worn with a conservative suit – maybe not a three piece suit or a tuxedo, but a vintage Rolex in stainless steel can be pretty versatile.

Lastly, there are true-blue casual watches. When I’m not in suits and sport coats, my wardrobe in the winter tends to revolve around Japanese denim, t-shirts, and workwear. Then maybe shorts and linen button-ups in the summer. I still mostly wear vintage Rolexes in these contexts, but I also think a chunkier watch such as a Panerai can be great. I have a Luminor (ref. 372) and Radiomir (ref. 249).

For a more affordable route, Seiko and Sinn are both great manufacturers. I like the Seiko 5 a lot. You can also get a Rolex Datejust nowadays for around $3,000, and they fit nicely into that semi-formal category. That’s one of those watches that can work across a range of wardrobes.

(photos via Gary and Yuko Fujita)


Takahiro Osaki of Liverano & Liverano

I wear suits and sport coats, but I like to have a style that feels a bit more casual and relaxed. The two watches I wear most are an IWC Flieger on a black dial (ref. IW3706-07) and a Rolex Explorer 2 on a white dial (ref. 16570). For me, size is very important. I don’t have a big wrist, so I don’t like watches that are too large. These two are manageable. The IWC is 39m; the Rolex 40mm.

I also like the name, Explorer! I travel a lot for work, and the two time-zone dial allows me to keep track of time in different parts of the world. It’s also just fun to see the different parts of the watch in action when I’m setting it on the plane. I bought one with a white dial because I thought it looks better with a white dress shirt. It’s a sporty watch, but also very elegant. 

My IWC is just really comfortable. It has a matte black dial and date window. Like my Explorer, I find’s really useful for work. It has a really smooth and accurate movement, and the black dial gives me some versatility between the two watches. I go between the two depending on my mood.

I like watches that can be worn with suits and sport coats, but also don’t feel too dressy. I like things that have a classic, sporty feel, but at the same time, aren’t too large. I think the above two models fit those requirements, but there are a ton of others. For a tighter budget, try a vintage Omega Genève, Citizen, or Timex Classic Camper. Even a Swatch Black Friday can be great.

(photo via The Armoury)


Kento Tsujimoto of The Real McCoys

I wear Army chinos and boots, heavy duty outerwear, and t-shirts. Many of the things I wear were never intended to be fashion items. They were functional clothes designed for work and utility. So I like watches that have the same backstory.

The watch I wear the most is my 1963 Rolex GMT Master (ref. 6542). I like the color and material used for the bezel and dial. For something a little more affordable, but can be worn in the same way, I think the Rolex Explorer I is really good.

(photos via Kento)