1. Rolex Oyster Perpetual (36mm or 41mm)

• Price: ~$6,500 to $7,500
• Why it’s a classic: Simple and clean, It is Rolex to the core. No date, no flash, just pedigree and polish.
• Great for: First-time Rolex buyers who want timeless over trendy.
• Seen as: A quiet flex. Shows taste without looking like you’re trying too hard.

2. Rolex Datejust (36mm or 41mm)

• Price: ~$8,000 to $12,000+
• Why it’s a status symbol: The Datejust is the go-to for finance guys. Dressy enough for work, durable enough for life. Steel or two-tone options, fluted bezel, and the signature Cyclops date window.
• Great for: New VPs, bankers, consultants, and deal closers who want polish and presence.
• Seen as Corporate-approved. Iconic and versatile.

3. Rolex Submariner (No Date or Date Version)

• Price: ~$9,000 to $12,000+
• Why it’s aspirational: Originally a dive watch, it is now a cornerstone of modern luxury. Sporty bold, but it’s still a classic.
• Great for Younger professionals or those seeking a more edgy and wristy presence.
• Seen as Confident. Shows ambition and awareness of status.

4. Rolex Explorer

• Price: ~$7,500+
• Why it’s a sleeper pick: Originally built for mountaineering but embraced by urban professionals. Less flashy and more purposeful.
• Great for: Men who prefer understated elegance over flashy style.
• Seen as Tasteful. For the watch enthusiast.

Pro Tip:

A new analyst or associate might aspire to a Submariner or Datejust but start with an Omega or Tudor. These brands still retain serious horological credibility but with a lot less financial impact.