This week we’re giving your wallet a break with a selection of watches under $5k. We’ve got low Asks on some classics as well as some relatively unknowns. For some people, 80’s hair bands never went out of style, and for others, the ‘oversized watch’ trend never died. If you fall into that camp, we’ve got you covered. All that and more on this edition of The Cultivated Wrist. Let’s dive in.

Omega Speedmaster Professional Moonwatch 311.30.42.30.01.005

There’s not much to say about the Omega Speedmaster that hasn’t already been said. It’s a watch that gained instant cult status when it went to the moon with the Apollo 11 crew, and every manned moon mission since. Omega has diversified the Speedmaster range into all manner of sizes, complications and materials in recent years, but there’s charm to the original variant that just can’t be replicated in all the spin-offs. Why settle for Joey when you can watch re-runs of Friends? When it comes to modern Speedmasters, this is as close to spiritual successor to the original as you’ll get. Right down to the hesalite crystal. With a low Ask listed at $3,600, this Speedy is more accessible than ever.

IWC Ingenieur IW323906

The IWC Ingenieur recently departed with its iconic 70’s port-hole design in favor of returning to its roots with a rounded case. The newest watches may cater to a broader audience, but we love the 70’s jam, hand angles and all. This example is a time-only affair with white dial and gold accents dials up the funk, and should age beautifully. If you love the Nautilus or the Royal Oak, you’ll find a lot to love here, especially the price. Current low Ask is listed at just $3,780.

Tudor Black Bay M79230B

The Tudor Black Bay is quickly becoming the de facto dive watch for shoppers not wanting to spring for a Rolex Submariner. It’s easy to see why, it faithfully holds to a design Tudor originally released in 1953 by getting the simple details right. The over sized hands and hour makers against a matte black dial make for superb legibility, and the dark blue bezel adds just enough color for some personality, but not enough to shout about it. The Black Bay is also COSC certified, and a truly capable dive watch, if you’re into that kind of thing. There’s a low Ask of $3,000 on this Black Bay, which is a steal considering it houses Tudor’s own movement.

Ernst Benz Chronolunar GC10311-DLC

Ernst Benz is an independent brand that specializes in large, pilot style watches that are, from time to time, endorsed by the likes of Mario Batali. This Chronolunar brings a variety of complications to the table, such day, date, month, and even phases of the moon. It’s also a chronograph. Thankfully the watch measures in at a whopping 47mm in diameter, so all those complications fit neatly within the vast real estate of the dial. Considering the veritable wealth of complications this watch offers, the current low Ask sits at just $3,760.

Zenith Pilot Montre de Aeronef Type 20 96.2431.693/21.C738

The Zenith Type 20 raised more than a few eyebrows when it was released in 2014 thanks to its 48mm case size. The watch’s intent as a true to its roots pilot’s tool is clear at the onset, from the massive Arabic numerals, flattened onion crown, and if you still don’t get the point, it’s got the word “Pilot” emblazoned on the dial at 6 o’clock. The watch comes on a bund-style strap to wrap the whole theme together. You can proudly release your inner pilot with the Type 20 without breaking the bank as it’s current low Ask is listed at $4,900.

Rolex Oyster Perpetual 114300

Bringing things back down to earth with the sizes, we’ve got this Rolex Oyster Perpetual which measures in at a far more approachable 39mm. It’s a simple three-hander that gives you everything you need and nothing you don’t. With a smooth polished bezel, oyster bracelet, and colorful dial options it’s tough to find a more flexible Rolex for under $5k. We like the grape, but you can also find the watch with blue or rhodium grey sunburst dials. There’s currently an Ask listed at $4,880 for this example.