atches are one of the few pieces of jewelry that any man can wear that is universally acceptable. Other jewelry like rings, earrings, necklaces and bracelets will have their detractors (myself included).
So for that reason alone, a watch is an accessory that every man should have. From a practical perspective, they are also nice for telling the date and time. But obviously not as required now that we’re carrying smartphones around with us all day long.
Just like I discussed in the series intro, there’s something amazing about owning a finely crafted piece of history and engineering perfection.
Whether you’re a watch guy or not, I think any self-respecting man should own a watch or two.
Before I get into the exact watches you should own, let me first answer the most common questions I get from clients, readers and viewers about watches:
What type of watch to wear with what outfits?
Suit = Dress Watch – you should never, ever wear a diving/chronograph/sport watch or anything but a leather or other hide strap with a suit. It drives me crazy when I see metal bracelets or nato straps with suits because they’re so casual in nature and they take away from the formality of a suit. It’s a SUPER amateur move.
Business Casual or casual outfits – Dress watch or Sport watch with a metal bracelet, leather/nato/rubber band. You can also wear a dress watch with them, but it depends on how “polished” your casual outfit is. If you’re in shorts and flip flops, that might not look right with a dress watch.
How to Match a Watch To Your Outfit
It’s pretty simple. If you’re wearing:
- A suit with black dress shoes and belt.
You should be wearing a dress watch with a black leather strap.
- A Suit with Brown dress shoes and belt.
You should be wearing a dress watch with a brown leather strap.
- Anything outside of a suit, even if you’re wearing dress shoes, you can wear any type of watch you’d like – that includes dress watches as well as any sport, chrono, diver, pilot, etc. type of watches.
What size should your watch be?
If you have a smaller wrist, around 6″, then go with a 40mm or smaller.
If you have average to a wider wrist, around 7″ or bigger, then go with a 40 to 44mm sized watch.
Most older watches, including Rolex’s diving watches, were 38mm or less, but they’ve since shifted to 40mm to follow the trend of larger watches now.
Traditionally, dress watches were made to be smaller and fit under your shirt cuffs, while diving or chronograph watches are bigger so they’re easer to read while doing the activities they were designed for.
It’s really up to your personal preference. I’m a little new school in that I think dress watches don’t need to be tiny – my favorite IWC dress watch (below) is very large for a dress watch, but I still love it. Unless your wrists are extremely small, then any size between 36 and 44mm will be fine. Which is fortunate because almost all watches fall within these sizes anyways. It’s when you get into vintage watches that the sizes tend to be smaller. So if you prefer a smaller watch, then vintage may be right for you.
How Many Watches Should You Own?
To cover all your bases, you should own 2 to 3 watches. You can absolutely get away with owning only one (which I’ll discuss shortly), but 2 or 3 different types of watches will cover you for all the outfits and scenarios you’ll encounter. A lot of my clients who are into watches own usually double or triple that amount, but we’re talking about the barest of essentials right now and anything else would be a speciality or just not used as much.
What Watches Should You Own?
1. Silver Dress Watch with a Black Leather Strap
Here’s the basics of what this watch should be. If you own one watch, this should be it. That way it’ll cover you for the most scenarios. You’ll also need a brown leather band to swap out as your outfit accessories dictate according to the matching rules I discussed earlier. So scroll to the bottom to check out my favorite band/strap site to get your extra straps.
Your black leather strapped watch should have the following features:
You want a silver case because, just like with the hardware on your belts, it’ll match with everything. If you were to get a watch with a gold or black case and black leather band, it won’t match as well or be too sporty to complement the rest of your essential wardrobe items.
As for the size of the case, that’ll depend on your preference and what looks best on you, but a classic dress watch is supposed to be very thin and small (sub 40MM, usually), but I’m a little new school in this regard and don’t mind a taller or larger case, something like the 44mm IWC cases is fine, but right on the edge, for me. Honestly, go smaller if you have a small wrist, and bigger, if you have a wider wrist.
The dial of your watch should be white because it’ll match perfectly with everything you could possibly throw at it. Black, blue, skeleton or other dials won’t match as well or will come off as too sporty or gaudy. I just think of all the sleezy salesman guys wearing their Movado watches at the bar after work – bleh.
Black Leather Strap
You can also use a leather alternative or other hide – kangaroo, ostrich, alligator, etc. The one thing you should never do is wear a nato or rubber strap with a suit. If I can be blunt – it looks like shit and is an amateur move. The quickest way to look like a teenager or style blogger is to wear a nato or rubber strap with every outfit. Those should be reserved for casual outfits only.
In regard to the stitching on the strap, I’ll forever dislike contrasting stitching, just like I do on wallets, so ideally, the stitching should match the color of the strap.
Subdials or complications
I’m a little new school in that I don’t believe a dress watch needs to have the cleanest dial possible. I don’t mind a few subdials or complications like a power reserve, subdial seconds, moon phase or month/day date. Just don’t go crazy and use a chronograph with a leather strap as a dress watch, please.
2. Silver or Gold Dress watch with a brown leather strap
The requirements for your brown leather-strapped dress watch are nearly identical to the black leather strapped dress watch above – with one major exception:
This is the one time when a gold case is acceptable because the dominant color of the accessories you’d be matching with would be brown, regardless of the hardware color of your belt. I’d still prefer a silver case if given the choice, but a gold case would work just as well.
If you have the budget for only one watch, or only want to own one dress watch, then make sure to get a brown band to swap out with your silver cased watch as your outfit accessories dictate. It’s a little bit of a pain, but not so much that this isn’t an option. Changing watch straps is quite easy and I have a great place to get really nice straps for cheap.
The Best Dress Watches
$12,000 – IWC Portugieser Automatic
$20,000 – Patek Philippe Calatrava White Dial
Bergmann Date 1933
Stuhrling Original Ascot
Bulova Dress Watch
Bulova Classic Watch
Tissot T-classic Tradition
Mondaine Evo Watch
Graf Zeppelin Hindenburg
Orient 2nd Generation Bambino
Rossling & Co Classic Automatic Bogart
Hamilton Intra Matic Silver Dial
Tissot Heritage Visodate Automatic
Frederique Constant Classic Index Automatic
Junghans Max Bill Chronoscope
Tag Hueur Carrera Calibre 5 Automatic
Junghans Max Bill Automatic
Cartier Tank Solo
Montblanc Heritage Chronométrie Automatic
Nomos Tangente 38 Datum
Breitling Transocean Chronograph 38
Omega De Ville Prestige
Cartier Ballon Bleu de Cartier
IWC Portugieser Chronograph
Jaeger Le-Coultre Reverso Classic Large Duoface
Omega De Ville Trésor Omega Master Co-Axial 40 MM
A lot of these watches come with black or brown straps.
$65.00 – Stuhrling Original Ascot II
$90.00 – Bulova Classic Dress Watch
$200 – Bulova Dress Watch
$220 – Tissot T-Classic Tradition
$230 – Mondaine Swiss Railways Evo
$260 – Graf Zeppelin Hindenburg
$300 – Orient 2nd Generation Bambino
$520 – Junkers Bauhaus
$530 – Hamilton Intra-Matic Silver Dial
$650 – Tissot Heritage Visodate Automatic
$650 – Frederique Constant Classics Index Automatic
$1,100 – Junghans Max Bill Chronoschope
$1,600 – Tag Heuer Carrera Calibre 5 Automatic
$1,800 – Junghans Max Bill Automatic
$2,500 – Cartier Tank Solo
$2,500 – Montblanc Heritage Chronométrie Automatic
$2,780 – Nomos Tangente 38 Datum
$3,600 – Omega De Ville Prestige Co-Axial 39.5 MM
$3,700 – Nomos Minimatik
$6,000 – Cartier Ballon Bleu de Cartier
$7,600 – IWC Portugieser Chronograph
$12,200 – Jaeger Le-Coultre Reverso Classic Large Duo Face
$15,000 – Omega De Ville Trésor Omega Master Co-Axial 40 MM
3. A Chronograph or Diving Watch
These watches are often called Sport watches, as well. You want this type of watch to round out your collection because it goes with any outfit from business casual on down. Unless you’re wearing a very sharp casual outfit, you shouldn’t be wearing a dress watch. That’s when a sport watch comes in to play. And please, for the love of all that is holy, please don’t wear your sport watch with a suit. I immediately know a guy doesn’t know much about looking good when I see a sport watch with a suit.
Here’s the details of what I look for in a good sport watch.
Black or Blue Dial
If I had my choice, I would choose a black or blue dial, with a slight edge to blue, as long as it’s more navy like Omega’s Speedmaster in Titanium (below) and not a royal blue like the Rolex Submariner in 16k white gold. The latter is just way too loud.
Silver Metal Bracelet
There’s nothing better for casual outfits than a diving or chronograph watch with a metal bracelet – in either titanium or stainless steel. Just like in the dress watches above, I prefer these materials and colors over a black or gold bracelet because it goes with everything and all the hardware on your belts, tie bars, etc. I also really love to see the metal bracelets swapped out for leather, rubber, perlon or nato straps, as well, but metal bracelets are a necessity for any sport watch – so you want to make sure it comes with that, first. For different watch straps, scroll down to the bottom of this article for my favorite place to get additional straps.
The Best Sport Watches
$11,000 – Omega Speedmaster – Moonwatch Omega Co-Axial Chronograph 44.25 MM
A quick note about the Speedster – the blue is much, much darker in person. The official images do it no justice.
$8,000 – Rolex Oyster Perpetual Submariner Date
Casio Super Illuminator Diver
Parnis p101506 Mechanical
Seiko 5 Sports Automatic Black Dial
Seiko 5 Sports Automatic Blue Dial
Orient Mako USA II
Steinhart Ocean 1 Black
Tissot V8 Quartz Chronograph
Borealis Bull Shark
Seiko Prospex Kinetic Dive Watch
Hamilton Seaview Date Blue Dial
Victorinix Maverick Stainless Steel Bracelet Watch
Longines Hydro Conquest
Christopher Ward C60 Pro
Hamilton Jazzmaster Seaview Chrono Quartz
Hamilton Seaview Day Date Auto
Tag Heuer Aquaracer Calibre 5
Omega Seamaster 300 Omega Master Co-Axial
Omega Speedmaster Moonwatch Omega Co-Axial Chronograph 44.25 MM – Steel on Steel
$75.00 – Casio Super Illuminator Diver
$80.00 – Stuhlring Aquadiver
$100 – Parnis p101506 Mechanical
$125 – Fanmis Submariner
$150 – $200 – Seiko 5 Sports Automatic (also in a dark blue version)
$400 – Orient Mako USA II (has blue & black options)
$500 – Steinhart Ocean 1 Black
$450 – Tissot V8 Quartz Chronograph
$450 – Borealis Bull Shark
$550 – Seiko Prospex Kinetic Dive Watch
$660 – Certina C024.447.11.081.00
$700 – Hamilton Seaview Day Date Quartz Blue Dial (Also make blue dial & automatic versions)
$700 – Victorinix Maverick Stainless Steel Bracelet Watch
$800 – Longines Hydro Conquest
$2,000 – Tag Heuer Aquaracer Calibre 5
$4,000 – Tudor Pelagos
$6,000 – Omega Seamaster 300 Omega Master Co-Axial
$6,000 – Omega Speedmaster Moonwatch Omega Co-Axial Chronography
$7,850 – IWC Aquatimer Chronograph
$15,000 – Rolex Daytona
The Best Watch Straps and Bands
First and foremost, there’s no substitute for OEM straps or bands. But a really close second is my favorite aftermarket strap/band site – CheapestNatoStraps.com. Don’t let the name fool you, they’re neither cheap, in terms of quality, and they make a lot more than nato straps. I’ve been swapping out watch straps and bands for clients for a long time now and this is the only place I go for aftermarket straps.
I talked to the owner, Sofie, and she was kind enough to offer you an additional 10% off your purchase if you use offer code: AshleyWeston
A big thanks to reader/viewer Travis and the team over at www.Horobox.com for letting me bounce thoughts and ideas off them and providing their expertise and insight for this story. Definitely check them out!