Dressing Up: The Most Expensive Cufflinks Money Can Buy

To some, the whole notion of cufflinks may seem a little absurd because they are so tiny that they are easy to lose. After all, plain old buttons are so much more practical and are attached directly to the shirt, which prevents them from falling off and getting lost. Nonetheless, to a great many others, cufflinks are the final piece of men’s wardrobe. Like many other fashion accessories, cufflinks convey a measure of style, personality, taste and social status.

Historically, cufflinks didn’t come into prominence until the 14th century when men’s sleeve ruffles emerged as a fashion statement. Initially, colored cloths or strings and ribbons were used to tighten their loose sleeves. Over time, more elaborate and attractive links were used to fasten these cuffs, transforming the ordinary sleeve fasteners into stylized and bejeweled cuff links.

The royal class is generally credited as being the driving force behind the evolution of cufflinks, especially during the reign of the Sun King himself, Louis the Great (Louis XIV, 1638-1715). His love of jewelry led to a whole collection of diamond cufflinks, rumored to exceed 150 pieces. His style was mimicked by members of the French royal court, and before long, by aristocracies across Europe.

However, it was not until the English Victorian era that cufflinks really took off, especially with the affluent middle class. Coats and jackets suddenly had to be accompanied by trendy cufflinks, and extra special ones were required for extra special occasions. Naturally, this led to an immediate explosion in design, choices of raw materials and of course, prices. For high society, cufflinks were crafted using steel alloys, gold and other precious metals, and were then monogrammed, bejeweled or even engraved with images, emblems and crests. Gentlemen from the middle class, nevertheless, can still look forward to beautifully and elaborately crafted cufflinks despite using less prized materials.

Over a century later, cufflinks are considered an essential part of haute couture, formal attire and business attire. Hundreds of fashions houses have exclusive lines dedicated to them, bearing an endless range of choices to fit every conceivable occasion.

10 Jacob & Co. Canary Diamond Square Cufflinks: $35,000.00/Pair


Jacob & Co. Canary Diamond Square Cufflinks

Designed by fine jewelers Jacob & Co, this formal cufflink is crafted in a minimalistic fashion meant to enhance the delicate beauty of the square 10.5 carat yellow canary diamond. Set atop a 14k white gold frame, the cufflink features an oval-shaped flip-back latch. The elegant design and soft colors makes this the perfect choice for the busy executive switching from work to evening wear.

9 Jacob & Co. 2-Tone Left and Right Diamond Cufflinks: $35,200.00/Pair

Jacob & Co. 2-Tone Left and Right Diamond Cufflinks

This two tone cufflink offers the ideal solution for edgy executives intent on standing out from the crowd. Crafted in intricate cubic designs using pieces of white and yellow canary diamonds weighing a total of 3.44 carats each, these cufflinks sport a simple whale back clasp. Paired with a dark jacket, these cufflinks are bound to get you a second look during meetings or outings.

8 Arfaq Hussain’s V2 Cufflinks: $39,007/Pair

Arfaq Hussain’s V2 Cufflinks

Featuring a golden crown decked with sapphires and diamonds laid on top of a striking double sword base made from 18-carat yellow and white gold, the V2 used to hold the title of the world’s most expensive cufflink. Designed by Arfaq Hussain, the former design director of London-based House of Gianni Vive Sulman, only seven V2's were ever made. Its most famous buyer was the King of Pop, the late Michael Jackson, who wore the V2 as part of his iconic pseudo-military outfit worn during the HIStory World Tour.

7 Phoenix by Givenchy: $70,000/Pair

Phoenix by Givenchy

Foundrie 47, a jewelry company which specializes in using steel extracted from firearms seized from warzones in Africa, launched its brand of cufflinks in 2011 with the introduction of the AK47 range (named after the rifle). A year later, the company collaborated with James de Givenchy to produce the Phoenix Collection, which in the words of its creator, “was inspired by the concept of the egg as a symbol of budding possibility.”

James, who is the nephew of fashion legend and founder of The House of Givenchy, Hubert de Givenchy, uses the steel from approximately 120 AK47 rifles to form the rose pedestal base for each of his cufflinks. Adorned with 47 conflict-free diamonds and inlaid with an 18k interior gold coating, the Phoenix is at once worn, jaded and extraordinarily beautiful.

6 Jacob & Co. Baguette Diamond Double Ended Football Cufflinks: $96,000.00/Pair

Jacob & Co. Baguette Diamond Double Ended Football Cufflinks

As far as football bling goes, this probably ranks as one of the most exquisite forms of expression. From players to coaches to officials, the football-shaped diamond arrangement, measuring a total of 15 carats, is augmented with an 18-carat yellow gold trimming that gives this cufflink relevancy despite its seeming flamboyance. In addition, the designer took into account the giant fingers of its target market with a double-sided chain back clasp for easy fastening.

5 Jacob & Co. Diamond Baguette Pentagon Cufflinks: $114,000.00/Pair

Jacob & Co. Diamond Baguette Pentagon Cufflinks

The understated design belies a stunning-level of craftsmanship as evidenced by the perfect symmetry of diamonds masterfully placed inside a dual pentagonal layer of 18-carat white gold. Using a combined total of 10 carats worth of diamond, the design also features an unobtrusive oval flip back fastener that maintains a modest appearance for the unassuming magnate.

4 Jacob & Co. Baguette Diamond Double Ended Basketball Cufflinks: $162,000.00 / Pair

Jacob & Co. Baguette Diamond Double Ended Basketball Cufflinks

If football players can have specialized cufflinks, then why can't basketball players? Using a total of 22.73 carats worth of white diamonds to adorn four spherical cuffs, along with a two tone white and yellow gold trimmings, this design is bound to turn heads. A loose one piece double sided clasp completes this eye-catching $162,000 cufflink.

3 King Edward’s VIII Cartier Cufflinks: $400,000/Pair

The legendary love story between King Edward VIII (1894-1972), and his commoner American wife, Wallis Simpson (1896-1986), probably ranks as one of the greatest this century. Facing objections from the British Parliament and the Church of England, King Edward voluntarily abdicated his throne in 1936 in order to marry Simpson.

In a 1987 auction organized by Sotheby’s, over $50.8 million worth of the couple’s memorabilia was sold, including one of Edward’s most treasured possessions - a pair of diamond cufflinks given to him by Simpson.

Designed by Cartier, the diamond and sapphire-encrusted cufflinks were part of a dress set that was eventually won by Syrian billionaire Wafic Said after a frenzied bidding. Legend has it that the cufflinks were engraved with the phrase ''Hold Tight”, an expression often used by King Edward in his love letters to Simpson.

2 Jacob & Co. Diamond Art Deco Cufflinks: $601,428.00/Pair

Jacob & Co. Diamond Art Deco Cufflinks

This artfully-designed vintage cufflink sports two massive white 6.05 and 5.90 carat diamonds encircled by smaller baguette diamonds weighing a total of 4.52 carats, laid on an 18 karat white gold frame. The symmetrical geometric lines and lavish shape enhances the already visible beauty of the two large stones; and the creators have rightfully targeted the piece to the discerning and competitive family heirloom market.

1 Jacob & Co. Emerald Cut Canary Diamond Octagon - $4,195,000/Pair

Jacob & Co. Emerald Cut Canary Diamond Octagon

Sometimes, a personal statement transcends beyond form, functionality and economy. Instead, it speaks of refinements, elegance and heritage. In the world of cufflinks, nothing can rival the statement made by Jacob & Co.’s emerald cut canary diamond octagon cufflink.

The central 10.76 carat diamonds are treated with the Asscher cut, resulting in wide facets and sharp, clipped corners, breathing fire into already gloriously magnificent, yellow Cape diamonds.

The entire piece consists of approximately 21.29 carats of diamonds in total, embedded on a polished 18-carat white gold structure with a whale flip-back latch. This truly is a gift fit for kings and merchant princes.

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