The Best Watches Around $1,000

The world of high-end horology often feels like an exclusive club reserved for the ultra-wealthy, but a recent collaboration between business mogul Kevin O’Leary and watch expert Teddy Baldassarre highlights a significant shift toward "attainable" luxury. O’Leary, famously known as "Mr. Wonderful," admits that his journey into entry-level pieces began after a Shark Tank producer challenged him to wear watches that young entrepreneurs could actually afford, rather than just the "piece uniques" that "nobody can get or afford". This philosophy centers on the idea that a watch is a tool to mark time and success, serving as a landmark for professional milestones such as a graduation or a first successful business deal. O’Leary, a self-described "dial guy," now frequently pairs rare pieces like a Credor or FP Journe with high-quality watches under $1,000, often wearing two timepieces simultaneously to track different time zones like New York and Abu Dhabi.

In a curated showcase of "insane value," Baldassarre introduced several pieces that challenge the notion that quality requires a five-figure investment. Among the standouts was the Seiko Recraft Series, a retro-inspired mechanical watch that retails for approximately $200, which O’Leary initially guessed would cost over $1,000. The collection also featured the Seiko Speed Timer "Pogue," a solar-powered chronograph with a copper yellow dial and "Pepsi" bezel that carries the lore of being worn by NASA astronaut William Pogue during the Skylab 4 mission. Other notable entries included the Unimatic UC4, a minimalist Italian design with 300 meters of water resistance, and the Hamilton "Murf," a cinematic favorite from the film Interstellar that offers an 80-hour power reserve and a "Calatrava vibe" for just under $1,000.

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The technical diversity of these affordable options is vast, ranging from the high-frequency accuracy of the Bulova Super Seville—which oscillates at 262,000 hertz—to the military-grade Marathon Navigator, a pilot’s watch featuring tritium gas tubes for constant illumination. For dive watch enthusiasts, the list included the Doxa Sub 200, a brand famously associated with Jacques Cousteau, and the Squale 1545, which draws on the brand's history of providing cases for extreme dive watches.

However, the ultimate winner of the day was the Formex Field, a titanium piece featuring a striking "Robin egg blue" dial and a patented on-the-fly adjustment system. O’Leary selected this as his top pick because its vibrant dial "looks stunning" from a distance and is capable of starting a conversation, which he views as the primary goal of any great watch.

Beyond the aesthetics, O’Leary emphasizes a disciplined approach to collecting, advising enthusiasts to never use debt or credit cards to purchase a watch they cannot afford. He also stresses the importance of diversification across brands and styles once a collection grows beyond the first piece. To address the rising market values of many watches, O’Leary has partnered with Chubb to launch Wonder Care, a specialized insurance product that allows owners to insure their pieces at current market prices rather than just the original purchase price. This ensures that as a watch appreciates like a piece of art, the collector is protected against loss or theft with the ability to secure a replacement. Ultimately, the message is clear: while no one strictly "needs" a watch, the desire to own one is rooted in the uniquely human need to celebrate life’s most meaningful moments.