The Six Most Expensive Harry Winston Earrings
The most expensive Harry Winston earrings pair important Burmese rubies, Colombian emeralds and diamonds with the house’s signature cluster settings and detachable designs.
Harry Winston earrings often begin with the stones. Large diamonds and colored gemstones are given room to define the design, while surrounding diamonds create structure without overwhelming the center stones. In pendent earrings, this approach can become especially dramatic, with substantial gems suspended beneath clusters of pear- and marquise-shaped diamonds.
The house also returned to ideas that made ambitious earrings more versatile. Detachable drops appear across different periods, while closely matched stones could turn a pair of earrings into a significant gemological achievement as well as a finished jewel. The most expensive Harry Winston earrings sold at auction since 2019 bring these ideas into focus, showing how the house adapted its approach to rubies, emeralds and diamonds of very different character.
The Most Expensive Harry Winston Earrings
| Harry Winston Earrings | Notable Features | Price (USD) |
|---|---|---|
| Ruby and Diamond Pendent Earrings | 20.19 and 18.68-carat unheated Burmese rubies; detachable pendants | $1.98M |
| Diamond Pendent Earrings | 10.35 and 10.32-carat D Color, Flawless emerald-cut diamonds | $1.67M |
| Emerald and Diamond Earclips | 21.60 and 21.11-carat Colombian emeralds; minor clarity enhancement | $1.64M |
| Fancy Light Brown-Pink Diamond Earclips | 12.41 and 11.15-carat natural-color diamonds; circa 1963 | $1.58M |
| Emerald and Diamond Pendent Earrings | 17.03 and 16.27-carat Colombian emeralds; circa 1970s | $913K |
| Diamond Pendant-Earclips | 9.63 and 7.66-carat pear-shaped diamonds; detachable drops | $693K |
1. Harry Winston Ruby and Diamond Pendent Earrings, $1.98M
This pair of ruby and diamond pendent earrings, with tops by Harry Winston, sold for 15.6M HKD in April 2023. The detachable pendants are set with oval rubies weighing 20.19 and 18.68 carats, each surrounded by oval and pear-shaped diamonds and suspended beneath marquise- and pear-shaped diamond cluster tops.
The scale of the rubies is notable on its own, but finding two stones of this size that could function successfully as a pair adds another dimension. SSEF, Gübelin and AGL all identified the rubies as Burmese in origin with no indications of heating, while AGL reported no clarity enhancement. The diamond-set tops are signed HW, allowing the ruby pendants to be detached from the Winston mounts.
2. Harry Winston Diamond Pendent Earrings, $1.67M
This pair of Harry Winston diamond pendent earrings sold for 13.2M HKD in October 2023. The detachable drops are set with emerald-cut diamonds weighing 10.35 and 10.32 carats, suspended from clusters of pear- and marquise-shaped diamonds. The platinum tops are signed Winston.
GIA graded both emerald-cut diamonds D Color and Flawless, with Excellent polish and symmetry. Their closely matched weights make the pairing all the more striking: instead of relying on elaborate settings, the design places two substantial step-cut diamonds at the center of the composition. Detachable drops allow the diamond cluster tops to be worn independently.
3. Harry Winston Emerald and Diamond Earclips, $1.64M
This pair of Harry Winston emerald and diamond earclips sold for 12.8M HKD in April 2026. Each suspends a step-cut emerald weighing 21.60 or 21.11 carats, accented by pear-shaped emeralds and diamonds. The platinum and 18-karat yellow gold mounts are signed Harry Winston and numbered.
Both Gübelin and AGL identified the two principal emeralds as Colombian in origin with minor clarity enhancement. Beyond their individual size, the close relationship between the 21.60 and 21.11-carat stones is central to the design. Rather than treating one emerald as the dominant gem, the earrings depend on two substantial stones working together as a balanced pair.
4. Harry Winston Fancy Light Brown-Pink Diamond Earclips, $1.58M
This pair of Fancy Light Brown-Pink diamond earclips by Harry Winston sold for $1.58M USD in December 2019. Dating to 1963, the earrings suspend pear-shaped diamonds weighing 12.41 and 11.15 carats beneath clusters of marquise- and pear-shaped diamonds. GIA determined both principal stones to have natural color, grading the larger diamond VS1 and the smaller SI1.
The earrings were created for Nenetta Burton Carter, whose relationship with Harry Winston resulted in a number of jewels made for her over the years. Pink held personal significance for Carter, and Winston selected these substantial colored diamond drops with that preference in mind. Although the earclips are unsigned, they are numbered and were accompanied by an authenticity letter from Harry Winston.
5. Harry Winston Emerald and Diamond Pendent Earrings, $913K
This pair of Harry Winston emerald and diamond pendent earrings sold for 7.2M HKD in September 2026. Dating to circa the 1970s, the earrings suspend pear-shaped Colombian emeralds weighing 17.03 and 16.27 carats beneath arrangements of pear- and marquise-shaped diamonds. Multiple gemological reports identified the emeralds as Colombian in origin with minor clarity enhancement.
The elongated pear shapes give this pair a different character from the step-cut emeralds seen earlier in the ranking, drawing the eye downward through the diamond-set composition. Although the earrings are unsigned, their history is supported by a pouch stamped Harry Winston and a copy of the original purchase receipt from Harry Winston S.A. of New York, dated July 6, 1971.
6. Harry Winston Diamond Pendant-Earclips, $693K
This pair of Harry Winston diamond pendant-earclips sold for $693K USD in June 2022. The detachable drops are set with pear-shaped diamonds weighing 9.63 and 7.66 carats, each topped by a round diamond and suspended from clusters of pear- and marquise-shaped diamonds. GIA graded the 9.63-carat diamond E Color and VS2 clarity, while the 7.66-carat diamond received D Color and VS2 clarity.
The construction allows the cluster surmounts to be worn independently once the pear-shaped drops are removed, giving the earrings two distinct configurations. The pair is numbered 5582 and bears the maker’s marks of François Tavernier, a maker for Harry Winston—an unusually specific detail that connects the finished jewel to its manufacture.
Harry Winston Earrings and the Art of the Pair
Harry Winston’s most important earrings often ask two exceptional stones to work as one jewel. Matching goes beyond carat weight: color, cut and overall presence need to hold their own across both sides of the pair. That challenge becomes more pronounced with substantial rubies, emeralds and diamonds.
The settings are often remarkably restrained in response. Diamond clusters frame or suspend the principal stones, while detachable elements introduce flexibility without distracting from the gems themselves. Across different decades and gemstone types, that balance between the stones and their setting remains central to the strongest Harry Winston earring designs.
Frequently Asked Questions About Harry Winston Earrings
What makes a pair of Harry Winston earrings important?
The gemstones are often the starting point, especially when a pair incorporates diamonds or colored stones of substantial size. Matching between the two principal stones also matters, while the design, period and strength of the attribution can add further context to the finished jewel.
Why are matched gemstones important in Harry Winston earrings?
Earrings require two stones to function together visually. As carat weight increases, finding gems with compatible color, cut and overall appearance becomes more difficult, making the quality of the pairing an important consideration alongside the individual stones.
Are detachable Harry Winston earrings more collectible?
Detachable construction can add interest when it is integral to the original design. Several important Winston earrings use removable drops so the diamond cluster tops can be worn independently, allowing the jewel to shift between a more elaborate pendent format and a shorter earring.
Do Harry Winston earrings need to be signed to be authentic?
Not necessarily. Some documented Harry Winston earrings are unsigned. Original receipts, authenticity letters, stamped cases or pouches, maker’s marks and other supporting documentation can help establish a connection to the house when a Harry Winston signature is absent.
What should collectors look for when considering vintage Harry Winston earrings?
Look closely at the principal gemstones and how successfully they have been matched, then consider the construction and attribution of the jewel. Gemological reports and period documentation can provide additional information about gemstone origin, treatment and the earrings’ connection to Harry Winston.
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