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Serpentine Diamond Engagement Ring Guide

Engagement Rings

Shopping for an engagement ring should be one of the most thrilling things you ever do. Yet somehow the process has become synonymous with being overwhelmed with too many options, too much conflicting information, and an industry that doesn't always prioritize your education over your purchase.

The clients who end up with rings they are still in love with twenty years later almost always have one thing in common: someone took the time to actually explain what they were holding, what made it extraordinary, and why it was right for them.

Whether you are picking out your own dream ring or shopping for the person you cannot wait to spend your life with, think of this as the conversation we would have if you walked through our doors today!

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Step 1: Learn What Actually Matters

Before we look at any specific stone, we begin by educating clients on the 4Cs - cut, color, clarity, and carat weight - because understanding how those factors work together is the foundation of making an informed decision. But at Serpentine, we also believe the certificate only tells part of the story. We want clients to understand what actually makes a diamond exceptional beyond the grading report: how a well cut stone performs in everyday lighting, how two diamonds with similar specs can look completely different in person, and why some stones immediately catch your eye while others fall flat despite sounding impressive on paper. Once clients can recognize those differences for themselves, they’re able to shop with a completely different level of confidence.

At Serpentine Jewels, we source stones the way a collector sources art: obsessively, selectively, and with a very clear point of view about what exceptional actually means. We’ve built relationships with some of the very best diamond and gemstone dealers in the industry, which gives us access to stones most clients would never have access to walking into a traditional jewelry store. We travel to Tucson, Las Vegas, and gem shows around the country specifically to hunt for excellent stones that offer outstanding value. If something comes through our door, it is because it met an incredibly high standard. That level of discernment is non-negotiable for us, and frankly, it is what every client should expect from whoever they buy from.


Step 2: Pick Your Shape

Diamond shape is one of the most personal parts of the entire engagement ring process, and there is no universally “best” choice. Our job is to help clients hone in on the shape that feels most like them while also understanding the tradeoffs that come with each cut, because shapes that look similar on paper can wear, sparkle, and perform very differently in real life.

Here are some of the engagement ring diamond shapes we source and design with most often at Serpentine Jewels, along with the reasons clients are drawn to each of them:

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Oval Diamonds

Oval diamonds are one of our most requested shapes for engagement rings. Clients love them for their elongated silhouette and soft, flattering look, and many ovals can appear visually larger than rounds of a similar carat weight depending on their proportions. The main thing we pay attention to with ovals is the bow tie effect, which is a dark shadow that can appear across the center of the stone depending on how it was cut. Some bow tie is normal, but in poorly cut stones it can become distracting very quickly. When an oval is proportioned well, though, it has a beautiful elongating effect on the finger that clients are consistently drawn to.

The Round Brilliant Diamond Engagement Ring with Heart Side Stones features a large round center diamond and two heart-shaped side diamonds, displayed against a white background.

Round Brilliant Diamonds

Round brilliant diamonds remain the industry standard for maximum sparkle and light return. They are the most mathematically optimized cut for brilliance and light return, and are also typically the most expensive per carat because demand is so high and the cutting process often preserves less of the original rough crystal. If sparkle is your top priority, a beautifully cut round is very hard to beat.

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Pear Shapes

Pear shapes are another longtime Serpentine favorite. They have the softness of an oval combined with the elongation and point of a marquise, which gives them a beautiful balance of elegance and edge. Thanks to their elongated silhouette and spread, pear shapes can appear larger than many other cuts of the same carat weight. Like ovals, cut quality matters enormously because pears can show bow tie shadows or uneven light performance if they are not proportioned well. You also want to pay attention to the symmetry of the shape itself. A beautifully cut pear should feel balanced, with a softly rounded end, a graceful point, and shoulders that match evenly from side to side.

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Radiants 

Radiants are a great option for clients who love the outline of an emerald cut but want significantly more sparkle. They have an incredible amount of brilliance and fire, which gives them a very lively, high-energy look on the hand. They also hide inclusions well, face up beautifully, and are especially striking in yellow and fancy colored diamonds because the facet pattern intensifies and concentrates color so effectively.

The Emerald Cut Diamond Engagement Ring with Cadillac Side Stones in White Gold features a central emerald-cut diamond accented by Cadillac-cut side stones, all set in elegant white gold.

Emerald Cuts

Emerald cuts have a completely different light performance than brilliant cuts. Instead of intense sparkle, they produce slower, broader flashes of light through long step-cut facets, giving them a quieter, more architectural elegance often associated with Art Deco jewelry. Their large, open table reveals far more of the stone itself, meaning color, clarity, proportions, and overall quality matter enormously in this cut.

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Marquise Diamonds

Marquise diamonds are especially popular among our clients right now because they create incredible finger coverage while offering a silhouette that feels slightly bolder and more fashion-forward than more traditional cuts. Some clients are drawn to softer, fuller proportions, while others prefer longer, sharper marquise shapes with a more dramatic feel.

The East-West Bezel Set Cushion Cut Diamond Engagement Ring features a large cushion-cut diamond in a simple bezel setting, displayed against a white background.

Cushion Cuts

Cushion cuts are one of the most versatile diamond shapes because they can vary so dramatically from stone to stone, but what unites them is their soft, rounded corners and pillowy outline. Some cushions have a brighter, more splintery “crushed ice” sparkle, typically seen in cushion modified brilliants, while others display chunkier facets with broader flashes of light, more commonly associated with cushion brilliants. Their proportions also change the overall feel of the stone enormously. Some are nearly square with a perfect 1:1 ratio, while others are more elongated and rectangular. Corner shape matters too - sharper corners create a cleaner, more tailored look, while softer corners can make a cushion appear more similar to an oval.

A close-up of the Antique Cushion Cut Diamond Solitaire Engagement Ring showcases a large cushion-cut diamond in four prongs on a simple silver band, set against a white background.

Antique Cuts

We are also seeing enormous interest in antique stones and antique cuts. Old Mine cuts were the precursor to the modern cushion brilliant, while old European cuts were the precursor to today’s round brilliant diamonds. Both were hand cut before modern technology existed, which gives them a completely different look from modern stones. Their facets tend to be larger, softer, and slightly more imperfect, often centered around an open culet that creates a distinctive floral pattern when viewed face up. The result is a warmer, more candlelit type of light return that many clients find more romantic and individual than modern cuts.

The Cluster Ring is bezel set with mixed shape white and fancy yellow diamonds, creating a vibrant, modern, and elegant design.

Unique Shapes

Beyond the traditional shapes, one of our specialties at Serpentine is sourcing stones with unusual cuts, silhouettes, and color. Many of our clients come to us specifically for kites, shields, movals, portrait cuts, rose cuts, antique-style pears, fancy color diamonds, and other collector-grade stones that fall outside traditional diamond categories. Those stones tend to have a tremendous amount of personality and often become the starting point for some of our most interesting custom projects.


Step 3: Choose Your Setting

The setting is where an engagement ring truly begins to take on its personality. This is the stage of the process where we introduce texture, proportion, and subtle design details that give a ring its individuality and sense of character. At Serpentine Jewels, every setting is custom made and built entirely by hand in New York specifically for the center stone it was designed around.

Here are some of our most requested setting styles and the reasons clients are drawn to them:

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Solitaire Settings

Solitaire settings are for someone who wants the center stone to speak entirely for itself. They have a clean simplicity that feels timeless, but truly great solitaires require an enormous amount of thought and proportion work to execute well. Prong shape, basket design, stone height, band width, and the way the diamond sits on the hand all become far more noticeable when there are no additional design elements competing for attention. When executed beautifully, a solitaire allows the quality and personality of the center stone to remain the focus entirely.

The Elongated Asscher Cut Sapphire Engagement Ring features a vibrant green sapphire center in 18K yellow gold, accented by a halo of round sparkling white diamonds.

Halo Settings

Halo settings can add presence, amplify sparkle, and make a center stone appear significantly larger. On the right ring, they can be incredibly beautiful, especially when the halo feels fully integrated into the overall design rather than overpowering the stone itself. We tend to gravitate toward halos with a little more individuality, like French cuts, baguettes, reverse-set rounds, geometric step cuts, or designs that precisely trace the outline of an unusual center stone.

We especially love halos around colored gemstones because they can completely transform the way a gem presents. A thoughtfully designed diamond halo can make colored diamond, sapphire, or other vibrant gemstone appear even richer and more saturated on the hand. The best halo settings create definition, contrast, and presence while still allowing the eye to remain focused on the center stone.

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Three Stone Rings

Three stone rings are one of our favorite categories to design because there are so many ways to personalize them. The traditional symbolism is past, present, and future, but they also create opportunities for unexpected combinations of shapes, proportions, and colored stones that give each ring its own unique point of view.

The Hexagonal Diamond Engagement Ring with Pavé Bezel and Band in 18k rose gold features a pavé bezel halo of diamonds and additional diamonds on the band for a dazzling look.

Bezel Settings

Bezel settings wrap metal completely around the stone, making them one of the most protective and structurally secure setting styles in fine jewelry. But beyond practicality, we love them for the way they transform the overall character of a ring. A bezel gives a stone a cleaner outline, stronger shape definition, and a slightly more tailored, architectural feel than traditional prongs. They are especially compelling with unusual diamond cuts and colored gemstones because the surrounding metal can really emphasize the geometry and presence of the center stone.

At Serpentine, many of our favorite settings are the ones that incorporate meaningful details in a way that still feels elevated and timeless. We have designed hidden birthstones inside bands, engraved motifs inspired by meaningful places or family symbols, custom-cut side stones that reference a client’s aesthetic, and settings engineered entirely around unusual diamonds that required something completely bespoke. Those small design decisions are often what make a ring feel truly yours rather than mass produced or pulled from inventory.

Metal choice also changes the overall personality of a ring more than people expect. White gold and platinum tend to make diamonds appear brighter and icier, while yellow gold adds warmth and softness, especially with warmer diamonds or antique stones. Rose gold sits somewhere in between and can feel especially flattering and feminine depending on the stone and the wearer’s skin tone.


Step 4: Bring the Ring to Life with the Right Team

The person guiding you through this process matters just as much as the ring itself. A great jeweler should be able to help you understand not only what is beautiful, but why it is beautiful, and guide you toward decisions that feel informed, thoughtful, and reflective of your taste.

Working with Ali is a very different experience from walking into a traditional jewelry store because she approaches engagement rings first and foremost as both a gemologist and a designer. Every project begins with the diamond or gemstone itself: how it interacts with light, how it’s cut, how it feels on the hand, and what makes it exceptional beyond the certificate. From there, the design process becomes about translating your taste into a ring that feels entirely your own, whether that means something timeless and understated, or bold and unexpected.

At Serpentine Jewels, we are known not only for the quality of our stones and craftsmanship, but also for the creativity of our designs. Every custom engagement ring is built entirely by hand in New York City by some of the very best craftsmen in the industry. When you work with us, you are not just working with one person - you have our entire design team involved every step of the way, helping refine proportions, source unusual stones, engineer custom details, and bring your vision to life in a way that feels truly bespoke to you.

Most importantly, the relationship does not end once the ring is delivered. We are here not only for resizing, cleanings, and annual checkups, but for future wedding bands, anniversary pieces, redesigns years later, and every chapter your collection evolves through over time.

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Begin Your Serpentine Journey

Every relationship begins with a conversation. Connect with Ali and her team for a private appointment at our New York City studio or Greenwich atelier — or virtually from anywhere in the world.