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The Romantic Return of the Diamond Bypass Ring

Here’s why this historic design is becoming one of today’s most coveted engagement styles.

Published: December 5, 2025
Written by: Meredith Lepore

diamond bypass ring — (Courtesy of Alder Fine Jewellery)

Though bypass rings first rose to prominence during the Victorian era in the late 19th century, they’ve never truly fallen out of fashion. Their elegant, dynamic silhouette has kept them relevant for more than a century—and recently, they’ve experienced a resurgence.

Bypass rings resonate especially with those seeking natural diamond engagement rings, drawn to the deep symbolism woven into their sculptural form. The two gently curving bands are often seen as representing separate individuals who meet and unite at the center stone.

“Many couples still like that meaning because it fits the idea of choosing a life together… the shape hints at partnership in a simple way,” Shelly Spence, curator at Grace Renee Gallery, told Only Natural Diamonds.

Meet the Experts

The Romantic Return of the Diamond Bypass Ring

Shani and Mikela Alder founded Alder Fine Jewellery in 2021, quickly establishing the label as a destination for contemporary, architecture-inspired diamond design. Their refined approach to proportion, silhouette, and multi-shape pairings has made them standouts in the modern jewelry landscape.

Shelly Spence is the curator at Grace Renee Gallery, where she has spent several years helping clients discover art and jewelry that reflect their personal style and story. With a background in fine arts and contemporary jewelry, she brings a trained eye and deep knowledge of design to every consultation.

Ahead, we explore the evolution of bypass rings, what to consider when shopping for one, and why the style continues to resonate in the modern era, thanks to its rare blend of timeless romance and contemporary elegance.

What Is a Bypass Ring?

Trumpet & Horn Diamond and Platinum Bypass Ring, $6,500, trumpetandhorn.com

In a bypass setting, the band curves around the finger and meets the center stone from two opposing directions. Rather than forming a perfect continuous circle, the shank sweeps upward to create an elegant cradle for the stone, resulting in a graceful, asymmetrical silhouette that feels both dynamic and refined.

The open, off-center lines of a bypass ring create a natural sense of fluidity, allowing light to reach each stone from multiple angles. As the ring shifts with the movement of the hand, natural diamonds catch and scatter the light, producing a vivid sparkle. “The ring appears to be moving because of the bypass shape… the ensemble as a whole has a delicate, harmonious, and romantic feel,” Spence says.

Bypass Rings vs. Toi et Moi Rings

While bypass rings and toi et moi rings are often grouped together, they are distinct in both structure and meaning. A bypass ring features a band that curves gracefully around the finger with its ends sweeping past each other, creating a sense of movement; a toi et moi ring, by contrast, is defined specifically by two center stones symbolizing “you and me.” Many toi et moi rings use a bypass-style shank, but not all bypass rings include two stones—making toi et moi a romantic subset of the broader, more architectural bypass category.

A Brief History of Bypass Rings

Jacqueline Kennedy wears her diamond and emerald toi et moi engagement ring in Washington, D.C. (Getty Images)

Bypass Rings, as we recognize them today, became especially popular during the Victorian era, but their core concept dates back much earlier. In ancient Rome, couples exchanged gimmel rings—rings composed of two (or sometimes three) interlocking bands that symbolized the joining of two individuals. While not identical to the modern bypass setting, gimmel rings share the same underlying symbolism: “you and me” coming together as one. By the late 19th century, this sentiment evolved into the sweeping, intertwined aesthetic that defined Victorian romance, cementing the bypass silhouette as an emblem of partnership and devotion.

As jewelry design entered the Art Nouveau period at the turn of the 20th century, bypass rings took on more ornate details. Jewelers embraced naturalistic motifs—vines, leaves, buds, and soft, fluid curves—that complemented the setting’s inherent sense of movement.

Bypass rings surged back into the spotlight in 1953, when Jacqueline Kennedy (then Jacqueline Bouvier) received her now-iconic Van Cleef & Arpels diamond and emerald toi et moi engagement ring. While technically a two-stone design, it follows the same bypass-style architecture, with the band sweeping toward each contrasting center stone. Jackie’s ring became one of the most influential engagement designs of the 20th century, sparking a renewed fascination with bypass silhouettes.

Jackie Kennedy's diamond and emerald engagement ring — Jackie Kennedy’s diamond and emerald engagement ring. (Photo by Pat Greenhouse/The Boston Globe via Getty Images)

Purchased for over $1 million, Jackie Kennedy’s ring featured a 2.84-carat Colombian emerald, a 2.88-carat emerald-cut diamond. The stones were mounted on a bypass-style band of yellow gold and platinum, accented with tapered baguette diamonds.

Anything Jackie Kennedy touched seemed to turn instantly to style gold, and her engagement ring was one of her earliest fashion-defining moments. In 1962—shortly before President Kennedy’s death—she had the ring redesigned, replacing the original baguette-cut diamonds with marquise-cut stones arranged in a laurel-wreath motif beneath the two main gems. Additional round brilliant-cut diamonds were added along the front half of the band. Van Cleef & Arpels set the two center stones in graceful bypass-style shanks, enhancing the ring’s fluid, intertwined silhouette.

This redesign was widely celebrated not only for its elegance but also for how it embraced the rising popularity of modern marquise cuts in the early 1960s.

Best celebrity engagement rings of all time Joan Crawford — Joan Crawford wears her bypass ring while posing with her husband, Alfred Steele, Chairman of the Board of Pepsi-Cola at the Fontainbleau Hotel in Miami Beach. (Getty Images)

Hollywood also played a role in elevating the bypass silhouette. When Academy Award–winning actress Joan Crawford married her fourth husband, Pepsi-Cola chairman Alfred Steele, in 1955, the story goes that Steele had forgotten to purchase an engagement ring ahead of the ceremony. To make up for it—and to deliver maximum impact—he surprised her with an eye-catching double-wrap band entirely set with baguette diamonds. Though more sculptural and modern than traditional toi et moi styles, the dramatic bypass form suited Crawford’s larger-than-life glamour and helped reinforce the bypass ring’s reputation as a bold, expressive choice in mid-century jewelry design.

Today, bypass rings have evolved into a sleeker, more streamlined form. Designers have minimized the open gaps and dramatic spacing that were popular during the Art Deco era, opting instead for tighter, more sculptural metalwork around the center stones. “Bypass rings have been part of Alder’s design story since we launched three years ago, and interest continues to grow,” note Shani and Mikela Alder, co-founders at Alder Fine Jewellery.

“Clients are drawn to the expressive, fluid silhouette—and increasingly excited to experiment with different diamond cuts within this modern interpretation of the classic style.”

How Diamonds Elevate Bypass Rings

Alder Fine Jewellery Multi-Shape Diamond Bypass Ring, $5,660, alderfinejewellery.com

Alder Fine Jewellery Amara Diamond Bypass Ring, $12,734, alderfinejewellery.com

Bypass rings provide a versatile canvas for natural diamond shapes and pairings. “Ovals, pears, rounds, and even heart-shaped diamonds all work beautifully — each cut brings its own character to the silhouette. Our multi-shape style is especially loved because the contrast instantly gives the ring personality, “ Shani and Mikela Alder tell Only Natural Diamonds.

They emphasized that the key is proportion and the angle of the setting—whether the stones are arranged east–west, set on a subtle tilt, or mirrored. “When the shapes are balanced and thoughtfully set, almost any pairing can create a harmonious, elegant bypass design.”

Taking that concept even further, many designers are now embracing mismatched diamonds as a fresh twist on the classic bypass silhouette. “Clients love that different shapes create a ring that feels expressive and personal, almost like two energies meeting in the middle. Our multi-shape diamond designs have become a popular collection for us — not only in bypass rings but also in tennis necklaces and bracelets — because they feel modern, a little unexpected, and still very refined,” said the Alders.

Below, some of the most popular combinations for natural diamonds in bypass rings:

Pear and Pear: A classic combination which draws the eye along the flowing curves of the band.

Round and Oval: The partnership of brilliance and elongated form results in a true masterpiece on your finger.

Emerald and Pear: The emerald cut paired with the taper of a pear stone creates a beautiful and precise design.

Old European Cuts: These antique cuts are having a major moment, and when partnered with the curved bypass bands, they bring an elegant second life to the ring.

What’s Driving the Bypass Ring Trend?

Ashley Zhang Jewelry Diamond Toi et Moi Pear Bubble Ring, $5,400, ashleyzhangjewelry.com

So why are we seeing a resurgence of the bypass ring—especially in natural diamonds? Part of the appeal lies in the broader embrace of vintage silhouettes and stones. Old mine and cushion cuts are having a major moment among celebrities—Miley Cyrus’s brand-new engagement ring, for example, features a cushion-cut natural diamond. At the same time, interest in nontraditional engagement rings continues to grow, making the asymmetry and movement of a bypass design feel especially fresh.

Recent celebrity choices have helped fuel the trend as well. Both Megan Fox and Ariana Grande have worn bypass-style engagement rings in the past (even if those relationships didn’t lead to weddings). And Kylie Jenner famously commissioned custom matching Toi et Moi rings—another variation of the bypass concept—for herself and her daughter.

megan fox 2022 celebrity diamond engagement ring — (Instagram: @meganfox)

The bypass ring is uniquely appealing because, while it offers the heirloom quality many couples are seeking, its sculptural form also lends itself to a sleek, almost futuristic aesthetic. “People want rings that feel different without going too far from tradition… It has a way of feeling modern and nostalgic at the same time,” Spence says.

These rings also allow for more personalization of ring elements than most other settings.”Today’s clients want pieces that feel individual rather than traditional. Asymmetry now feels intentional and expressive, and bypass rings naturally lend themselves to that sculptural, wrapped-around-the-finger look,” the Alders say.

Bypass rings also open the door to creative metal mixing. One side of the design can be crafted in platinum while the other is rendered in rose or yellow gold, creating a striking, high-contrast effect. The possibilities for unique pairings are nearly endless. The Alders noted that yellow gold remains the most popular choice, as its warmth complements the retro bypass silhouette particularly well.

Choosing the Right Style for You

When selecting a ring for everyday wear, its beauty matters—but so does choosing a design that aligns with your lifestyle. Bypass rings can be wonderfully wearable, though certain interpretations are better suited to specific daily routines.

Elevated or open bypass designs do require some specific considerations for everyday wear. An elevated design means the stone’s table is set higher, making the ring more susceptible to being caught or snagged.

Comfort also depends on how the ends of the bypass, known as the terminal points, are finished. They should be smoothly rounded and shaped to follow the natural curve of the finger. When crafted well, the terminal points sit comfortably against the skin, preventing any pressure or snags.

Whether you opt for a more minimalist setting or more of a statement piece, the Bypass Ring’s stunning silhouette with its unique blend of motion and symbolism will never disappoint.