Often heralded as the “Jeweler to the Stars,” as one of the first to recognize the branding power of lending glitzy pieces of fine jewelry for red-carpet events, Harry Winston is known for his eye for fine gemstones. It’s a reputation that extends to the celebrated engagement rings that have long emerged from his international salons.
At the end of the Great Depression, De Beers Consolidated Mines had been focusing their marketing efforts on generating consumer demand for diamonds. So they contracted the Philadelphia agency N.W. Ayer & Son to build an advertising campaign that emphasized a tangible connection between diamonds and romance.
At the time, diamonds were considered a luxury purchase and people were generally disinterested in them anyway, but with the support of N.W. Ayer’s laser-focused print and radio strategy — and later, its “A diamond is forever” tagline — young men across the United States soon became convinced that diamond engagement rings were critical to a successful courtship. For women meanwhile, the link between diamonds and the emotional bond of marriage had been solidified. Diamond sales skyrocketed, and De Beers was successful in ultimately rendering diamonds a must-have for Americans considering popping the question.
Today, the appeal of vintage engagement rings especially endures with millennials looking for something unconventional to symbolize their love. (A range of buying guides can be found on 1stDibs for those in the market for antique engagement rings, vintage engagement rings or Art Deco engagement rings.)
Harry Winston had already garnered acclaim for his talents by the time the diamond engagement ring had taken center stage thanks to De Beers’s changing social attitudes about the precious stone. He opened Harry Winston Inc. in 1932 and acquired the 726-carat uncut Jonker diamond in 1935. In 1944, he became the first jeweler to dress an Oscar nominee when he loaned diamond jewelry to Jennifer Jones for the Academy Awards ceremony.
Harry Winston is still favored by celebrities and influencers and is among the big names in jewelry that remain go-to sources for quality classic and contemporary engagement rings. Ben Affleck proposed to Jennifer Lopez with a 6.10-carat radiant-cut pink diamond engagement ring from the brand in 2002, spurring an interest in fancy-colored diamonds.
Winston is said to have favored emerald-cut diamonds because of how the wide facets generously flatter the stone, prioritizing its clarity in a classic platinum ring setting. On 1stDibs, browse stunning Harry Winston engagement rings by stone, stone cut and more.
Harry Winston 2.30 Carat Round Brilliant Cut Diamond Three-Stone Engagement Ring
By Harry Winston
Located in Chicago, IL
An iconic Harry Winston three-stone engagement ring showcasing timeless elegance and exceptional craftsmanship. Crafted in platinum (PT950), this classic design features a magnificen...
Diamond, White Diamond, Platinum
Platinum 950 Harry Winston Natural Single Diamond Band Ring
By Harry Winston
Located in New York, NY
Platinum 950 Harry Winston Diamond Band Ring Metal Type: 950 Platinum Total Item Weight: 4.9 Grams Ring Size: 3.5 (Resizable) 1: Prima...
Diamond, Platinum
Harry Winston 18k White Gold Channel-Set Baguette Diamond Eternity Band Ring
By Harry Winston
Located in Guangzhou, CN
Embodying the unrivaled glamour and exquisite craftsmanship of the "King of Diamonds," this authentic Harry Winston eternity band is a timeless masterpiece. Beautifully handcrafted i...
Harry Winston The One Platinum Oval Halo Engagement Ring 1.40 CTW
By Harry Winston
Located in Chicago, IL
An exquisite Harry Winston “The One” platinum engagement ring, showcasing the maison’s legendary craftsmanship and timeless elegance. At the center sits a captivating oval brilliant-...
Diamond, White Diamond, Platinum
Harry Winston, 1.17 Carat Round Brilliant Diamond Engagement Ring
By Harry Winston
Located in Chicago, IL
Elevate your jewelry collection with this exceptional Harry Winston diamond ring, featuring a stunning 0.75 carat round brilliant cut cente...
Diamond, Platinum
Harry Winston Platinum Cushion Cut Diamond Ring
By Harry Winston
Located in Chicago, IL
An elegant and refined ring by Harry Winston, centered by a GIA certified natural cushion modified brilliant-cut diamond weighing 1.05 carats, graded F color and VVS2 clarity. The d...
Diamond, White Diamond, Platinum
Harry Winston 4.29 carat Platinum Cushion Diamond Ring
By Harry Winston
Located in Chicago, IL
An exceptional signed ring by Harry Winston, crafted in platinum and centered with a superb cushion-cut diamond of remarkable quality. The center stone weighs 3.2 carats, graded D c...
Diamond, White Diamond, Platinum
Vintage Harry Winston Platinum & Antique Cushion Diamond Ring 11.56ctw GIA F/VS2
By Harry Winston
Located in Newport Beach, CA
We are very pleased to present this truly remarkable and rare vintage GIA Certified Harry Winston Platinum & Antique-Style Cushion Cut Natural Diamond Ring. This exceptional Harr...
Diamond, Platinum
Harry Winston Platinum Sapphire and Diamond Ring
By Harry Winston
Located in Zurich, CH
Stunning sapphire and diamond ring by Harry Winston. Discover the epitome of elegance with this exquisite ring crafted by the renowned jeweler Harry Winston. This lovely piece is co...
Diamond, Sapphire, Blue Sapphire, Platinum
Harry Winston Round Brilliant Diamond Ring in 18K White Gold
By Harry Winston
Located in Chicago, IL
This extraordinary Harry Winston Platinum Round Brilliant Diamond Pavé Engagement Ring showcases the House’s unrivaled mastery in selecting and setting the world’s finest diamonds. A...
Diamond, White Diamond, Platinum
Harry Winston Oval Diamond Engagement Ring & Pave Wedding Band Set
By Harry Winston
Located in Chicago, IL
Harry Winston Oval Diamond Engagement Ring & Pave Wedding Band Set This exquisite Harry Winston bridal set showcases a total of 1.53 carats of na...
Diamond, White Diamond, Platinum
Harry Winston Oval-Shaped Diamond Micropavé Halo Engagement Ring
By Harry Winston
Located in Chicago, IL
This exceptional Harry Winston engagement ring features a GIA-certified 1.51-carat oval brilliant diamond of the highest pedigree. Graded D color and VVS2 clarity, the center stone d...
Diamond, White Diamond, Platinum
Harry Winston Platinum Cushion Diamond Ring
By Harry Winston
Located in Chicago, IL
Harry Winston Platinum Cushion Diamond Ring This exceptional Harry Winston ring is a true collector’s piece, showcasing timeless elegance and masterful craftsmanship. Center Stone:...
Diamond, White Diamond, Platinum
Extraordinary Legacy in Diamond Form Harry Winston 28.13ct Masterpiece
By Harry Winston
Located in Chicago, IL
An Extraordinary Legacy in Diamond Form: The Harry Winston 28.13ct Masterpiece When rarity meets refinement, the result is nothing short of legendary. This original Harry Winston cre...
Diamond, Emerald, Platinum
Vintage Harry Winston 2.02 Carat Diamond Engagement Ring GIA, circa 1980s
By Harry Winston
Located in Simpsonville, SC
Elevate your love story with this extraordinary Vintage Harry Winston Diamond Engagement Ring, a true testament to the timeless allure of one of the world's most prestigious jewelers. Crafted in the 1980s, this piece features a stunning 2.02 carat round brilliant cut diamond of impeccable quality, exuding the enduring elegance and craftsmanship synonymous with the Harry Winston legacy. At the heart of this exquisite ring is a resplendent 2.02 carat round diamond, certified by the Gemological Institute of America (GIA) as an E color with a VS1 clarity. This exceptional diamond, with its brilliant white hue and remarkable clarity, is a testament to Harry Winston's commitment to sourcing only the most exceptional stones. Flanking the center diamond are six tapered baguette diamonds, 0.74 carats total diamond weight, each meticulously selected to complement and enhance the brilliance of the centerpiece. These side stones add a touch of sophistication and symmetry, creating a balanced and harmonious design. The classic round brilliant-cut center diamond, paired with the geometric precision of the baguette side stones, epitomizes the enduring elegance that defines Harry Winston's creations. The ring's design is a celebration of clean lines, symmetry, and a commitment to showcasing the inherent beauty of the diamonds. Lastly, the hallmark of a Harry Winston setting lies in its gracefully curved prongs. Crafted in the finest platinum, these prongs are meticulously fashioned to create an elegant embrace around the diamond. Instead of the more traditional single prong per side, this setting features two prongs on each corner of the center stone. This double prong design not only offers additional security for the diamond, but it also adds a distinctive touch of refinement to the overall aesthetic that is a signature element of Harry Winston rings. This vintage Harry Winston engagement...
Diamond, White Diamond, Platinum
Harry Winston Platinum 4.05 cts Diamond Ring
By Harry Winston
Located in New York, NY
Harry Winston platinum RBC diamond engagement ring with GIA certificate center diamond 4.05 cts E color SI1, with 2 heart shape diamond approx 1...
Diamond, Platinum
Harry Winston 4.22 Carats Vs2 Diamond Platinum & 18K Gold Ring Papers
By Harry Winston
Located in Great Neck Plaza, NY
This elegant ring is a true masterpiece, featuring a remarkable 4.22-carat round white diamond celebrated for its superior clarity and color. The diamond is artfully set in a classic...
Diamond, 18k Gold, Platinum
Harry Winston 12.00 Carats Pear Shape Diamond Three-Stone Engagement Ring
By Harry Winston
Located in New York, NY
A classic Harry Winston diamond engagement ring, showcasing a 12.00 carats pear shape diamond certified by GIA as F color and VV...
Diamond, Platinum
GIA Certified 2 Ctw Harry Winston Engagement Diamond Ring Platinum Three Stone
By Harry Winston
Located in Puyallup, WA
This three stone Harry Winston diamond engagement ring is crafted from platinum. It features three natural diamonds. The center diamon...
Diamond, Platinum
Harry Winston Platinum 0.71 ct Diamond Solitaire Engagement Ring
By Harry Winston
Located in Southampton, PA
One can't deny the exquisite elegance of this diamond engagement ring. The 2mm slender band is fashioned from platinum and topped with a 0.71 ct diamond center stone. The solitary ce...
Diamond, Platinum
Harry Winston Platinum Diamond Engagement Ring 1.76ct E/VVS1 GIA Cert
By Harry Winston
Located in Mayfair, London, London
A glamorous platinum diamond engagement ring by Harry Winston from The One collection. The ring is set to the centre in a four claw mount with a cushion cut diamond weighing 1.76ct, ...
Diamond, Platinum
Harry Winston 2.88 Carat E VS1 Round Diamond Solitaire Ring
By Harry Winston
Located in Geneva, CH
2.88 Carat E color and VS1 clarity according to Gubelin Report 11010171. Round cut Diamond White Gold Solitaire Ring. Made by Harry Winston.
Diamond, White Gold
Harry Winston the One Round Brilliant Diamond Micropavé Platinum Ring US 4.25
By Harry Winston
Located in Tokyo, JP
■Item No.: 30450618 ■Brand: HARRY WINSTON ■Name: The One, Round Brilliant Diamond Micropavé Engagement Ring ■Material: 1P Diamond (D0.72ct D-...
Diamond, Platinum
Vintage Harry Winston GIA Certified D-Color Pear Cut Diamond Ring in Platinum
By Harry Winston
Located in London, England
A beautiful GIA certified vintage Harry Winston pear cut diamond ring set in platinum. The piece is predominantly set with a GIA certified 0.74 carat pear cut diamond. The diamond i...
Diamond, Platinum
Harry Winston 0.71 Carat Round Diamond Solitaire Engagement Ring in Platinum
By Harry Winston
Located in Philadelphia, PA
Harry Winston platinum round diamond solitaire engagement ring. The center stone of this ring is a 0.71 carat round diamond with E color and VVS2 clarity accompanied by a GIA report...
Diamond, Platinum
Harry Winston Tryst Platinum GIA Certified 0.87 E VS1 Diamond Engagement Ring
By Harry Winston
Located in Los Angeles, CA
DeKara Design Estate Designer Collection Metal- 95% Platinum, 5% Iridium. Stone- GIA Certified Round Diamonds E Color VS1 Clarity, 0.81 Carats. 4 Round E-F Color VS1 Round Diamonds, 0.06 Carats. GIA Diamond Report Number 2136028272 An amazing entirely handmade Harry Winston Tryst...
Diamond, Platinum
Harry Winston 1.18cts Brilliant Diamond Engagement Ring GIA E VVS1 Triple Ex
By Harry Winston
Located in Dallas, TX
Exceptional Harry Winston diamond engagement ring featuring a superior triple Ex round brilliant diamond of 1.18 carats in a timeles...
Diamond, White Diamond, Platinum
Harry Winston Solitaire Diamond Engagement Ring in Platinum, D VS
By Harry Winston
Located in Honolulu, HI
Harry Winston Solitaire Diamond Engagement Ring in Platinum features a round brilliant cut diamond D color, VS clarity weighing 0.57 carats. The diamond has excellent cut, symmetry a...
Diamond, Platinum
Harry Winston Ring. Princess Diamond Solitaire PT950 Platinum Band.
By Harry Winston
Located in Port Charlotte, FL
Authentic Harry Winston Ring Princess Cut Diamond Solitaire with a square wide band. Comes with Original Harry Winston Case. Comfort Fit PT950 Platinum 2.5mm by 2.5mm princess c...
Diamond, Gold, Platinum
Harry Winston Ring. Comfort Fit Harry Winston Wedding 4mm wide Band.
By Harry Winston
Located in Port Charlotte, FL
Authentic Harry Winston Ring Comfort Fit Platinum Wedding Band. PT950 Platinum Size 7.5 4mm wide 8.3 grams Engraved inside with personal note. Can be removed if requested for free.
Diamond, Platinum
Harry Winston GIA Certified Engagement Ring in Platinum with Diamond Box Papers
By Harry Winston
Located in Miami, FL
Engagement ring designed by Harry Winston. A contemporary elegant engagement ring, created in the city of New York by the jewelry house of Harry Winston. This modernist piece have been crafted in solid .950/.999 platinum with high polished finish. Diamonds: Mount in the center in a eight-prongs setting, with 1 round brilliant cut diamond of 0.56 carats, F color, VS-1 clarity. Weight: 3.8 Grams, (2.44 Dwt). Size: 5 and can be sized. Hallmarks: Stamped with the maker's mark, the platinum assay mark, the serial numbers and signed, "©HARRY WINSTON 235635 PT .950". Collateral: It is accompanied by the designer's dossier, the presentation jewelry box and the original sales receipt. Collateral: This ring is accompanied with a diamond report from the Gia gem...
Diamond, White Diamond, Platinum
Harry Winston Diamond Ring. Round Diamond Engagement Solitaire PT950 Platinum.
By Harry Winston
Located in Port Charlotte, FL
Authentic Harry Winston Ring Diamond Engagement ring. Comfort Fit, with Eternity diamond shank. PT950 Platinum 0.75ct Brilliant round Cut diamond. VS1 E color Size 4.5 4.3 grams
Diamond, Gold, White Gold, Platinum
Harry Winston Ring. Round Diamond Solitaire PT950 Platinum Band.
By Harry Winston
Located in Port Charlotte, FL
Authentic Harry Winston Ring Round Cut Diamond Solitaire with a comfort wide band. Comfort Fit PT950 Platinum 2.5mm round cut diamond. Size 5 3mm wide 5.3 grams
Diamond, Gold, 18k Gold, White Gold, Platinum
Harry Winston .56 Carat VVS1/F Diamond Solitaire Platinum Engagement Ring
By Harry Winston
Located in Southampton, PA
Platinum .56ct Diamond Solitaire Engagement Ring by Harry Winston. With 1 round brilliant cut diamond VVS1 clarity F color. Cut, Polish, Symmetry Excellent Fluorescence NONE This ri...
Diamond, Platinum
Harry Winston 1.03 ct Cushion Modified Diamond Engagement Ring
By Harry Winston
Located in New York, NY
Harry Winston 1.03 ct Cushion Modified Diamond Engagement Ring PRIMARY DETAILS SKU: Z153048 Listing Title: Harry Winston 1.03 ct Cushion Modified Diamond Engagement Ring Condition D...
Harry Winston 0.55 ct Diamond Belle Engagement Ring
By Harry Winston
Located in New York, NY
Harry Winston 0.75 ct Diamond Belle Engagement Ring PRIMARY DETAILS SKU: Z146040 Listing Title: Harry Winston 0.75 ct Diamond Belle Engagement Ring Condition Description: Retails fo...
Platinum
Harry Winston Ring. Round Diamond Solitaire PT950 Platinum Band.
By Harry Winston
Located in Port Charlotte, FL
Authentic Harry Winston Ring Round Cut Diamond Solitaire with a comfort wide band. Comfort Fit PT950 Platinum 2.5mm round cut diamond. Size 7.5 3mm wide 5.8 grams
Diamond, Gold, 18k Gold, White Gold, Platinum
Harry Winston Platinum and 18K Rose Gold 0.72ct Diamond Ring #5211
By Harry Winston
Located in Southampton, PA
A stunning two-toned design makes this Harry Winston ring a charming addition to any luxury collection. At the center of the Platinum band, a 0.72 carat heart-shaped Diamond serves a...
Diamond, 18k Gold, Rose Gold, Platinum
Shopping for the right antique, new or vintage engagement ring can prove daunting. Whether you’re looking for that perfect Art Deco engagement ring, an antique Edwardian period engagement ring or a fashionable contemporary alternative, it’s important to choose a style that speaks to you.
Rings have long been signifiers of marriage and committed relationships. The modern diamond engagement ring can be traced back to 1477, when Archduke Maximilian of Austria commissioned an expensive diamond ring for his betrothed. Diamond rings subsequently became extremely popular among the European aristocracy. Later, during the Victorian era, the popularity of diamond engagement rings had filtered down to the middle class, owing to the increasing accessibility — and affordability — of gold and diamonds.
Authentic antique Victorian-era engagement rings were frequently set in rose or yellow gold and they are highly collectible. Designs for Victorian engagement rings often featured repoussé work and chasing, in which patterns are hammered into the metal. Diamonds were likely to be small rose- or old-mine-cut (the ancestor of today’s cushion-cut) stones. The former are often associated with antique styles like Victorian or Georgian, as rose-cut diamonds are uncommon in modern jewelry. The diamonds were typically set in a group of five in a band or as a solitaire.
Victorian-era engagement rings also saw other gemstones accompanying diamonds. Small seed pearls and moonstones were popular. Other sentimental and romantic motifs such as hearts and stars took hold as well. When Prince Albert became engaged to Queen Victoria, he gave her a serpent ring with emerald eyes, her birthstone. This initiated a widespread craze for snake jewelry.
In 1886, esteemed American luxury firm Tiffany & Co. introduced its solitaire diamond design, which is still among the most popular styles of engagement rings. The Tiffany Setting raises the stone above the band on six prongs, allowing its facets to catch the light and reflect through the stone.
French jewelry house Cartier, which pioneered the use of platinum in fine jewelry and helped define Art Deco, sought to render the diamonds in their engagement rings and other rings as brilliantly as possible. The brand’s timeless Solitaire 1895 engagement ring gave the impression of delicate lace.
Edwardian and, afterward, Art Deco engagement rings that followed in the wake of Queen Victoria’s death in 1901 would be characterized by complex geometric designs and platinum settings. Owing to the Art Nouveau movement, nature was a major theme for Edwardian jewelry, while the diamond ring designs of the Art Deco period were inspired by Cubism as well as ancient Egypt. Art Deco engagement rings are bold and colorful and feature gems cut in nontraditional ways.
Engagement rings designed during World War II were made from two-toned metals and smaller stones. Large stones were scarce, and platinum was reserved for the military. Postwar engagement rings were intended to be simpler and focused on the beauty of the diamond. In 1947, De Beers Consolidated Mines, with the support of Philadelphia ad agency N.W. Ayer & Son, introduced the slogan “A diamond is forever” in a marketing campaign that emphasized a connection between diamonds and romance. Diamond sales skyrocketed, and diamond engagement rings became intertwined with the post–World War II marriage boom, which coincided with the ascension of specific diamond cuts.
The round brilliant cut, which consists of an astounding 58 facets, continues to be the most popular cut to this day. Jewelers such as Harry Winston had already gained a reputation for his talents by the time the De Beers campaign debuted, and he is said to have favored emerald-cut diamonds.
For everything from understanding the 4Cs to choosing between antique, vintage, contemporary and custom styles, get expert tips to help you find just the right ring. Additionally, explore our buying guides for a close look at antique engagement rings, Art Deco engagement rings and vintage engagement rings.
When you’re ready to mark your momentous occasion, find a vast collection of engagement rings on 1stDibs.