This is going to be a highly debatable list. It’s going to be far too short of a list. That’s also why it’s going to cause some annoyance amongst sneakerheads and time geeks alike. First of all, there isn’t room for all the iconic trainers of the past — you will find either your favorite shoe or even brand missing — and why I paired the shoe with a certain watch was a very subjective process. This is not exact science people, it’s a gut feeling. But it comes from a true love for both sneakers and watches, so please keep that in mind. So, with that disclaimer out of the way, here we go! The 11 most iconic Sneakers and the watches that go with them.

Before we really start, please take note that your favorite sneaker might not be on the A-team. There are eleven players in a football team, and since I don’t want to bench anyone or anything, this is the number of players I’m fielding, end of story! Sorry to inform you that Finnish brand Karhu is not playing and so is the Saucony Jazz — pretty neat kicks, but also a bit too “New Balancy” if you ask me. No Brooks either or Diadora or Kangaroos. Maybe they will make the cut for the B-team.

… no Puma Drivers Shoe I would match to a TAG Heuer Link Senna. Get over it.

Speaking of the B-team. Other sneakers still in the race to make it to the second team include the Nike Cortez, the Onitsuka Tiger Tai Chi — Bruce Lee famously wore these shoes with a matching tracksuit in the movie “Game of Death” and would pair nicely with a yellow gold Datejust IMHO — and the quirky Puma Speedcat driving shoe that I would match to a TAG Heuer Link Senna. Okay, now let me introduce you to the watch/shoe combinations who did make the cut.

1. Converse All Star Chuck Taylor — Hamilton Khaki Field Murph Auto

We start way back in 1917 when the Converse Rubber Shoe Company introduced an indoor gym shoe you now see on the feet of punks and office clerks on their day off. The white canvas colorway Converse introduced was named Non-Skid. Doesn’t ring a bell? They also made a brown version they called All-Star. 17 years later the Converse All-Star shoes received the final upgrade to get to the name they still use: Chuck Taylor’s name was also added to the logo.

The 11 Most Iconic Sneakers And The Watches That Go With Them

It only seems logical to pair the All-Star Chuck Taylor to the Hamilton Khaki Field Murph Auto. There’s a bit of creamy lume on the black dial coupled with the crisp, classic layout that makes the most of an aged colorway. The dial is uncluttered and the price is just under €900. This matches the affordable yet undeniable quality of the famous Converse shoe.

2. Adidas Stan Smith — Glashütte Original Sixties Chronograph

Although the Adidas Stan Smith tennis shoe was introduced in 1971, it wasn’t actually new back then. It was just a clever bit of marketing to put the name of the tennis star on a pair of trainers. In truth, Adidas had been making the same sneaker since 1964. It was definitely an inspired idea. The tongue featured an image of Stan Smith but not his name. That final detail changed in 1977. Lately, the shoe has regained popularity and was re-released in uncountable fashionable versions.

The 11 Most Iconic Sneakers And The Watches That Go With Them

No one plays tennis in them anymore but a pair of Stan Smiths feels right at home in an informal, and even a slightly more formal setting (if paired correctly). They’re well-accepted and a safe choice. Dare I say they’re a typical exponent of German casual chic? The perfect match to a Glashütte Original Sixties Chronograph with a green dial to match the Stan Smith’s most famous colorway.

3. Vans Era — Cartier Tank Solo

I started with All-Stars, switched to Vans, and ended up with… Well, I still wear Vans, a lot. The brand was founded by Paul Van Doren, an American of Dutch descent who died earlier this year at the age of 90. In 1976 Vans collaborated with skateboarders to create the sturdy Vans #95, the shoe we now know as the Era style — my favorite style. The padded ankle lining makes them comfy to wear and the variety of fun colorways helped make it the skateboarder shoe. And if you still can’t find the right color, you can go custom. I ordered a custom-made colorway with a leopard pattern combined with black and gray checkers just last summer.

The 11 Most Iconic Sneakers And The Watches That Go With Them

Anyway, I would pair my Vans Era’s to a Cartier Tank Solo. What?! Hear me out! A skater is an eclectic being at heart, and the iconic shape and style of the watch represent the stylish and chic elements of the skater’s character. Plus, there’s nothing quite like dressing down such a classy watch, “sticking it to the man” in true rebellious skater fashion.

5. Nike Air Force 1 — Rolex GMT Master II “Pepsi”

I was told that hip-hop tycoon Jay-Z loves his Air Force 1’s. So he wears them a lot. But he only ever wears the same pair once! That’s because he doesn’t like the way they wrinkle. I totally understand the sentiment, but I’m not Jay-Z. So what I do is walk with care and only short distances and give my low-top version of the AF1 proper R and R to recover from a day on my feet. The problem with the AF1 that debuted in 1982, is that it doesn’t look good when it gets too beat up.

The 11 Most Iconic Sneakers And The Watches That Go With Them

But getting beat up was exactly what happened to the AF1 on the basketball courts across New York City where they got the nickname “Uptowns”. Experts say that the AF1 started sneaker culture as we know it today. The big, bulky, brash Nike Air Force 1 is as relevant as ever, something that also goes for the Rolex GMT-Master II. No matter what model you pick, a vintage one or the new Reference 126710, it has an in-your-face style that will be recognized and never gets old.

6. Nike Air Jordan 1 — Patek Philippe Nautilus

I’ve seen Michael Jordan sport a Roger Dubuis Excalibur Spider Pirelli Automatic Skeleton (white edition) in the fantastic Netflix documentary The Last Dance, but that watch doesn’t really match the 1985 Air Jordan 1 at all. The first pair appeared on the court in 1984 and were actually banned from the NBA because they broke the league’s uniform rules. Michael Jordan kept wearing them regardless of the $5k fine every game. I guess he didn’t have to pay that out of his own pocket, and even if he had, it wouldn’t have put much of a dent in his paycheck.

The 11 Most Iconic Sneakers And The Watches That Go With Them

The Air Jordan 1 marked the beginning of a vast number of Jordan shoes — the 3, the 6, and the 11 are my personal favorites — that are now sort of regurgitated. Retro is not only king in the world of watches, it also rules in sneaker country. Anyway, the GOAT — both the player and the shoe deserve that title — should be paired to a Patek Philippe Nautilus, the GOAT when it comes to luxury sports watches. Jordan was once spotted wearing a rare Nautilus Chronograph Ref. 5976/1G 40th Anniversary Limited Edition. Yes, the one with the rather awkward “1976 — 40 — 2016” writing on the dial that also features diamond hour markers. I think a more sober Ref. 5711 suits the shoes better, but no way I’m not going to argue with the GOAT’s pick.

7. ASICS Gel Lyte — Casio G-Shock GX-56

Functionality first. In 1987 runners were all excited about the arrival of something new, the GEL-Lyte running shoe. Japanese company ASICS put out advertisements in running magazines that read: “Speed freaks, we’ve got your number… it’s 9.9.”  Nine point nine ounces that is. That’s 280.6 grams for all us who prefer the metric system. And back in 1987 9.9 ounces was feathery light for a shoe. Something else important was the use of α-gel to absorb shocks. And that same gel found its way into the Casio G-shock GX-56 models to protect the movement/module from shocks. The GX-56 got the nickname “King” because of its large size, but also because its extra resistance to shocks wouldn’t “dethrone” the watch.

The 11 Most Iconic Sneakers And The Watches That Go With Them

Both the GEL-Lyte and the Casio G-Shock GXW-56-1AER are still around, so pairing a Japanese can-do-all watch with a pair of ASICS running shoes is more than natural. And on top of that, it’s also materially correct. The red α-gel shock Casio uses, at four points inside the King, is visible around the display.

8. Nike Air Max 1 — Rolex Submariner

The 1986 Nike Air Max 1 was designed by the legendary Tinker Hatfield — the Gérald Genta of sneaker design — who found inspiration in the Pompidou Center in Paris. As we speak the latest Air Max 1 release — based on the second version of the Air Max 1 that debuted in 1987 — a collaboration with Dutch sneaker store, Patta, that dropped last week, is a hyped-up and already sold out collector’s item. Point made regarding relevance and timelessness.

The 11 Most Iconic Sneakers And The Watches That Go With Them

Something else timeless is the Rolex Submariner. Doesn’t matter if it’s a “Sub” from ’86 or the latest version; they don’t age and they seem hotter than ever before. Both the gray market for watches and sneakers have gone a little wild lately. The interaction between eager collectors and clever sellers push prices of popular watches and sneakers through the roof. It happened to the “Sub” and it will happen to the Air Max 1 × Patta too.

9. New Balance 574 — Omega Speedmaster Moonwatch

I have ‘em, in burgundy. Yes, they are dad shoes, but then again, I am a dad. The New Balance 574 that debuted back in 1988 as an affordable running shoe, grew out to be a casual best-seller. It was intended for light workouts, never for running, but worked best when walking. That may sound a bit dull, but there were plenty of colorways in the beginning — you can never go wrong with navy blue, gray, or beige! At first, the 574 was a very conservative-looking, take-no-offence, suburban-style shoe for sure.

The 11 Most Iconic Sneakers And The Watches That Go With Them

Anyway, the 574 with the big “N” on the side, is a steady shoe in every way, and one that got funkier because of brighter colors made available over the years. But no matter what color you give a 574, it is, in essence, a dad shoe. A well-made, respectable, and versatile trainer. A shoe that is very hard to dislike. Just like an Omega Omega Speedmaster Moonwatch. The 574 has always been the 574. Yes, it had some updates and upgrades, but its core has remained the same. And the same goes for the Moonwatch. The latest version in its most basic iteration with a closed case back and Hesalite crystal is the watch equivalent to a 574 that is in stores today.

10. Reebok Pump — Breitling Chronomat

I never wanted them. I could never afford them. The 1989 Reebok’s Pump sneaker first hit stores with a $170 price tag attached. I was a Jordan guy anyway, so I just shrugged my shoulders and walked away. I thought they looked clunky, but I have to admit they were impressive too. And a little bit silly, but definitely impressive. The sneaker’s pumping mechanism in the shape of a basketball in the tongue was certainly avant-garde. Inspired by ski boots, the idea was to create a custom fit by inflating a bladder inside the shoe.

The 11 Most Iconic Sneakers And The Watches That Go With Them

And so was basketball legend Shaquille O’Neal, who had his own Pump shoe line called the Shaq Reebok attack line. The Shaq Attack 1–4 shoes were released throughout the ’90s. And you know what too was hot in the ’90s? Breitling Chronomats in steel and gold! Do I really need to explain the connection between a Breitling Chronomat UTC in steel and gold and a pair of Reebok Pumps? Fine, I’ll do it anyway. The watch is the shoe, the UTC module; the pump device. Make sense? I thought so!

11. Adidas Yeezy Boost 350 V2 “Zebra” — Hublot Big Bang Unico All Black Sapphire

The 2017 Zebra Yeezy Boost 350 V2 is a modern sneaker icon, no doubt about that IMHO. Music bigshot Kanye moved from Nike to Adidas and soon began creating a sneaker for the German brand. He started with the Ultraboost and then went nuts in a good way. The Yeezy Boost 350 V2 “Zebra” is one of the highlights in the Yeezy collection. They’re impossible to not spot and the colorway is spot on — you can’t go wrong with black and white with a touch of red, now can you? I’m also referring to the original Jordan 1, of course. These shoes have been restocked six times so far and still, there’s not enough of them.

The 11 Most Iconic Sneakers And The Watches That Go With Them

Since Kanye is a dedicated follower of fashion the watch Yeezy’s go best with is a watch from self-proclaimed fashion watch brand Hublot. The extravagant but somehow understated and monochromatic Big Bang Unico All Black Sapphire would match just nicely.

The 11 most iconic Sneakers and the watches that go with them: the final whistle

And there you have it, a (highly debatable) list containing 11 of the most iconic Sneakers and the watches that go with them according to me, ends right here. I’m sure the list will continue in the comments section. Please feel free to discuss amongst yourselves, criticize the coach that fielded, what was in my opinion, the best possible and strongest line-up, or put together an alternative team.

Better still, why don’t you capture your favorite sneaker/watch combination in a snapshot and send it to me at [email protected] so I can put together another team of 11 fitting combos?

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