Why The Hamilton Pilot Pioneer Mechanical Is Your Next Watch [Updated 2025]

Welcome back to 'Your Next Watch', a WatchGecko series that looks at the watches you might be considering buying and breaks them down based on our real honest hands-on experience with them.

Today we have Hamilton’s follow up to the Khaki Mechanical, the 2019 Pilot Pioneer. Hamilton has looked towards their supplement of Hamilton W10 watches to the armed forces (specifically the Royal Air Force) from the 70s with this release. Watches from this time period needed to be legible, durable as hell and compact. So, let’s see if Hamilton has kept those key features and made them relevant for modern wrists…

When discussing the Khaki Mechanical previously we talked about the watches ability to feel like a genuine authentic field watch from the history books and, to be honest, the Pilot Pioneer is actually better suited to that statement.

The watch comes in at 36mm wide with a lug-to-lug length of 42mm and a thickness of 10mm. And I know what you’re thinking. ‘At 36mm this watch is just too small”. To be honest, you’re right, it is...on paper. These statistics don’t translate well to actual wrist time which I believe is a good thing.

It’s true that watches have started to become smaller with the slowing down of the big watch trend and ‘the rise of vintage’ but 36mm hasn’t quite become the norm yet.

The Hamilton harnesses a tonneau shape to the case which means we’re not so reliant on the case width to quickly determine a watches wrist presence. As this watch is essentially a 1 for 1 of an original military watch from the 70s the design feels relatively familiar.

The black dial keeps things simple and naturally suitably W10-like with just hours, minutes and seconds being presented to the wearer seen through the mineral crystal. Pencil/sword hands, Arabic numerals and a clean railroad seconds track complete the dial of the watch.

On the topic of the dial, the addition of the grain texture is welcomed and simply beautiful. It adds another dimension to the watch, oozing character. The Khaki Mechanical’s flat matt dial feels a little lacklustre on this in comparison...

The watch also comes with a vintage coloured lume for both the hands and indices, something which although many of us have become immune to the presence of is still welcomed and makes perfect sense here. Through the solid case back we have the H-50 hand-wound movement which is also found in the Khaki Field Mechanical and with 80 hours of power reserve, is pretty hard to knock. It feels smooth and reliable on the wrist, zero complaints here.

For this on wrist segment, The Hamilton Pilot Pioneer receives a special road test as we head over to Germany. Travelling is heavily reliant on timing to ensure you’re in the right place at the right time; this suits the Hamilton down to a tee. Its distinct, clear dial means that quick glances down to the wrist to make sure a train isn't missed or there is plenty of time remaining before a flight are made a lot more efficient.

The watches shrunken size also means it is incredibly comfortable and unobtrusive. 50% of the wearable thickness is down to the crystal, which in day to day wear it’s very easy to forget you’re even wearing the watch as the physical steel visible is so minuscule. The most prominent outcome of this is the watches’ ability to slip under jacket sleeves easily. Surprisingly it is refreshingly versatile as well. Throw it on the right strap and you'll be able to go from day to evening attire effortlessly. Sure it's not a patch on the Cartier Tank or a Calatrava, but it's not embarrassingly inappropriate.

So, the Pilot Pioneer is commendably effective as a travel watch, but how does it perform day in day out? Well, if I’m honest, it's much of the same here. The power reserve at 80 hours is extremely generous to comfortably sit in a rotating collection. The lack of date may bother some wrists, but I wouldn’t have it any other way (something that would surprise myself from a couple of years ago as a traditional avid date window fan).

Sure, the watch is relatively simple in aesthetic, but it is by no means boring. It’s a great conversation starter and feels right at home with the increase in people wearing traditional styles of watches at the moment.

So, what are we not so crazy about on the Pilot Pioneer? What (if we could) would we change or feel would benefit the watch if it was possible?

• The hands - Bypassing their historical accuracy for a moment the hands on the watch are fully polished and also flat in their design. This results in hands that in certain light can be more difficult than they should be to distinguish which is which. I believe a reason for this being even more obvious is down to how legible everything else on the watch is.
• The case size won’t be for everyone  - Although we’ve discussed our enjoyment of this smaller size, it will almost certainly still put people off. It's very easy to come to a predetermined decision on a watch based on the dimensions mentioned in online listings and reviews. We'd recommend getting hands-on with one of these pieces if you're still not sold on the size. I'm sure it will change your mind.
• No drilled lugs - Now although this isn't a historically correct feature, I did enjoy the inclusion of drilled lugs on the Khaki Mechanical and feel it could be justified here. I'm sure it would ruckle feathers with the purists out there, but if you're considering this watch yet you want something original you would more than likely go out and find exactly that. Considering that this watch is now worn on modern wrists I feel Hamilton could pull it off.

I think a lot of people reading will be comparing this to the Khaki Mechanical; and rightfully so. The Khaki Mechanical is just less than half the price of the Pilot Pioneer. Coming in at £400 (at the time of writing) with sapphire crystal, as well as a larger more conventional size, I can see why many would be attracted to the Khaki Mechanical. However, sometimes (actually a lot of the time with watches) how something makes you feel overrides a price tag.

In the grand scheme of all things watches, for not a lot more money, I find this little Pilot Pioneer speaks to me more than the Khaki Mechanical. The charm and appeal it exudes to me feels more approachable and relatable to me as a collector.

The watch looks great on a range of straps (no gappy lugs here) it's more comfortable, more legible, less reflective and comes with the added bonus of versatility (which is very hard to ignore).

As I part with the Hamilton Pilot Pioneer I’m left with a positive reminiscent feeling. In a world where many people are wearing watches coming in at 40mm+, watches that are this humbling & compact size are just too charismatic to ignore. Imagery of Elvis, Andy Warhol and Winston Churchill all wearing small watch always come to mind when I wear this watch. It was a time when men wore smaller watches and owned the look. A time when watches didn’t rely on size alone for people to take note of what was on your wrist.

And at the end of the day, the only required task we ask of a watch is to tell us the time. The Hamilton Pilot Pioneer does this is in a useable, approachable & 'no frills' way.

Explore more about the Hamilton Pilot Pioneer and Khaki Mechanical here on their website. 

This article was written by Tim Vaux in 2019 and edited by Safie Agar-Hutton in Februrary 2025. Changes were made to the imagery and products featured. Tim Vaux is no longer associated with WatchGecko Magazine.