It is that time of year, where half the country is seeing signs of spring and the other half is still digging themselves out of snow. Clocks are getting ready to move forward, and millions everywhere are getting ready to fill out their brackets for some of the best few weeks in sports. We didn’t think the friendly head-to-head competition should be limited to the court, so we are bringing back Watch Madness.

Over three weeks we will be stacking thirty-two luxury watches up against each other until we have our winner. You can play along for free and could be wearing the winning watch when it is all over.

In the bracket you will see some perennial favorites, but like any good tournament, there are some cinderella stories that we think are poised to go deep into the rounds.

Here are the first sixteen matchups:

Cartier Pasha de Cartier vs. Weiss American Issue Field Watch

The Weiss is an American-made beauty. The watch is designed, manufactured, and assembled in Los Angeles, California. It has a hand-painted white-dial with black markers. The hands are black oxide that have been treated with luminescent paint for legibility in the dark. It features a small subdial with a sweeping seconds hand, an exhibition caseback and comes fitted on an olive green canvas strap.

The Cartier Pasha made its debut in 1985 as a modern luxury sports watch. Its round bezel was a departure from Cartier’s signature look. This Pasha has a black dial with white markers and Arabic numerals. The diamond-shaped hands are luminous for visibility and it has a unidirectional rotating bezel. The screw-down crown is a fluted and the watch sits on a stainless steel bracelet.

TAG Heuer Carrera vs. Maurice LaCroix Masterpiece

The TAG Heuer Carrera is inspired by racing and has a classic design with a contemporary feel. This Carrera has steel hands and markers. It’s an automatic wind chronograph and sits on a stainless steel bracelet. It’s a perfect introduction to racing watches.

The Maurice LaCroix story is younger than many of its industry counterparts as it began in 1975. Yet, the Masterpiece holds its own. This watch has a gray dial with steel hands and markers. It has three subdials and sits on a black leather band. The subdials track the day and date, and the power reserve. It also contains a moonphase complication, elevating the watch’s look.

Rolex Oysterquartz vs. Cartier Ronde Solo

The Rolex Oysterquartz debuted during the quartz crisis of the 1970s and 1980s. It took Rolex five years to create the movement and the result was a stunning addition to the Rolex line. This stainless steel watch has a silver dial and markers. It features steel hands with luminosity and a cyclops date window. Unlike many other Rolex models it has a smooth, polished bezel.

The Cartier Ronde Solo is classically elegant and has Cartier’s distinct look. This watch features a white bezel with black roman numerals for the hours and black minute markers around the center ring. It also has black 24 hour (GMT) markings and Cartier’s signature blue steel, sword hands. The watch has a black leather band easily dressing it up or down, keeping it effortlessly classic.

TAG Heuer Formula 1 vs. OMEGA Seamaster

The TAG Heuer Formula 1 was the first watch released after TAG bought Heuer in 1986 and became TAG Heuer. This watch is full stealth mode with a black bezel, dial and leather strap. It has three silver subdials for the chronograph complication and luminous steel hands. Red accents around the bezel, hands, and subdial give it an added touch of cool. This watch is perfect for any racing enthusiast.

The OMEGA Seamaster receives quick notability as James Bond’s watch but it is OMEGA’s oldest model and a fan favorite. This quartz model has a black dial with luminous dot and dash markers. It has stainless steel Bond hands with luminescent edges and tips and is fitted on a steel bracelet. You may not be Bond in this watch, but you will sure feel like him.

Nomos Tangomat vs. IWC Portofino

Nomos is a small German brand known for their minimalist and clean designs. This Nomos has a gray dial with a small subdial. Its accenting markers are subtle, yet striking. There is a small date window at the six o’clock position and it comes on a black leather strap. This watch is simple enough to go with a tee, but sleek enough to outfit a suit.

The IWC Portofino is a favorite among both men and women. It has an uncluttered dial, and takes inspiration from the pocket watch. This Portofino has a white dial with silver markers and hands. There is a small date window at the three o’clock position and it comes on a black leather strap. It is a simple, yet striking timepiece.

Breitling Blackbird vs. TAG Heuer Monaco

The Breitling Blackbird is a hefty pilot’s chronograph, and named after the Lockheed SR-71 plane. This Blackbird has a black dial with three small subdials and a large date window. It has luminous hands and markers for visibility, and comes on Breitling’s signature stainless steel bracelet. You may not have your pilot’s license, but this watch will make you feel like you can take to the sky.

The TAG Heuer Monaco just exudes cool. Steve McQueen wore the Monaco during the filming of Le Mans, and it’s been iconic ever since. This Monaco has the signature square case with a black dial and silver and white luminous markers. The two subdials are also square and it sits on a leather strap. You don’t have to race cars to be into this chronograph.

OMEGA Speedmaster Racing vs. Cartier Roadster

The OMEGA Speedmaster Racing hearkens back to the early days of the Speedmaster, long before it was worn on the moon. This version has a black dial and bezel, with three textured subdials. The luminous hands and markers are steel and white and comes on a stainless steel bracelet. Sturdy and steadfast, this watch is perfect whether you are racing cars, or racing to the office.

The Cartier Roadster is a classic racing watch with a bit of a twist. The case is neither totally square nor round. This Roadster is a study in monochromatic styling. The dial is white with black roman numerals and minute marks. The hands are white with black edging and there is a black date window at the three o’clock position. The case is black with a steel edging giving it an extra sleek look. Fastened on leather, this watch is a pure work of art.

Tudor Submariner vs. IWC Flieger Chronograph

The Tudor Submariner gives a nod to its cousin the Rolex Submariner, but can stand on its own. This version has a blue dial and bezel with a cyclops date window at the three o’clock position. The markers are a series of luminous dots and triangles which give the dial a striking look. The hands are stainless steel with luminosity for maximum visibility. It is water resistant to 200m and comes on a stainless steel bracelet. It is a perfect beginner’s dive watch.

The IWC Fliegler Chronograph is an often forgotten IWC model. This chronograph has a busy dial, but seems simplistic in its black and white color scheme. The dial is black with three subdials and two windows for the day and day. The markers are a combination of Arabic numerals and tick marks in white. It comes on a stainless steel bracelet and is perfect watch to take you from the day to night.

These are the first eight of our watch madness matchups. Each timepiece has its own unique and enviable merits, making it hard to choose the winner of their head-to-head matchups. Be sure to check out the other eight matchups in Watch Madness Part Two to set your brackets and determine this year’s winner.

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