We’re back with the fourth installment of our popular Three-Watch Collection Under $5,000 series. We’ve already seen Ilya’s, Mark’s, and Hung’s picks. Today, Sean?one of worn&wound’s longstanding writers and hardcore automotive enthusiast?breaks down his three.
A quick refresher on the parameters before we get started. We chose $5,000 as the cap for the simple reason that $5,000 is generally regarded as a point of entry into luxury. So rather than drop all that coin on a single watch, we thought it?d be interesting to see how our team plays around with that number. Furthermore, the choices aren?t limited to specific categories of watches. Our contributors can choose watches they?d like based on their needs and personal preferences. Finally, for the sake of consistency, all watches currently being produced have to be valued at their MSRP. Vintage or recently retired models should be based on the average market rate. Without further ado, let’s get to it.

OMEGA SPEEDMASTER AUTOMATIC 3510.61 ?RED SCHUMACHER? ~ $2,000
This was an easy one. I?m a huge chronograph geek, and if you?ve ever seen my Watches and Formula 1 series you?ll know I?m an even bigger racing geek. The Speedmaster Schumacher sits right at the crossroads of these two great passions for me. The Omega Speedmaster Automatic, in my opinion, is a serially overlooked option in the chronograph segment. While it may not have the cachet of the Moonwatch, the reduced 39mm ...