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When Charlize Theron wore a mismatched pair of mega-diamond earrings to the Academy Awards in February, social media went into overdrive. Echoing the recent tide of populist sentiment, some asked whether it was appropriate for the actress to be wearing stones that big (including a 26-carat heart-shaped diamond and a 25-carat pear shape, both from Chopard) and, obviously, that costly.

When four jewelers with more than 60 years of collective red carpet experience gathered in late April at the headquarters of The New York Times, I asked them that same question, and some others.

Greg Kwiat became chief executive of Fred Leighton in 2009, when his family’s diamond design company acquired the vintage specialist — a red carpet presence since the mid-1990s.

Colby Shergalis is vice president for marketing and communications at Forevermark US, a relative newcomer to celebrity jewels. The sustainably sourced loose-diamond business, owned by De Beers, was established in 2008. It made its red carpet debut that same year, when Nicole Kidman wore a L’Wren Scott-designed diamond sautoir necklace with 1,399 carats of Forevermark diamonds to the Oscars.

Monique Péan, an independent designer based in New York, has achieved a strong following in Hollywood, where her prehistoric-chic designs featuring materials like dinosaur bone, conflict-free gems and recycled metals resonate with ethically minded celebrities. Michelle Obama, Natalie Portman and the “La La Land” director, Damien Chazelle (who asked Ms. Péan to create the ethereal diamond jewels worn by Emma Stone’s character in his Oscar-winning film), all have championed her work.

And Martin Katz is a Hollywood veteran, having established his Beverly Hills-based company in 1988.

The conversation touched on subjects including the value of red carpet loans and memorable moments. Mr. Katz was something of an agent provocateur, often leading the group back to the touchy yet unavoidable topic of paid appearances.

“It’s cold today,” he said. “Most of the celebrities don’t even know who they’re wearing.”

Let’s start with the 2017 season. Greg, you scored a coup when the “Loving” star Ruth Negga wore Fred Leighton at the Golden Globes: a gold bracelet designed to look like a shirt sleeve buttoned by a 25-carat Gemfields ruby.

GREG KWIAT: Gemfields approached us and asked us if we might be willing to design something for Ruth, working with her stylist, Karla Welch. We thought it was an interesting opportunity to work with rubies.

Halle Berry, Janelle Monáe and Octavia Spencer all wore Forevermark diamonds to the Oscars. Can you quantify the impact of those placements?

COLBY SHERGALIS: It’s hard to quantify exact metrics. We do look for spikes in search, visits to our website and social media coverage. But there’s also a tremendous opportunity to build aspiration for the brand with these high-profile celebrities.

Monique, you’ve had an especially exciting year. Beyond working with “La La Land,” the “Moonlight” star Mahershala Ali wore cuff links you designed for the United Nations Women HeForShe initiative to the Academy Awards.

MONIQUE PÉAN: HeForShe is a really important campaign supporting gender equality, so it was amazing to have such a prominent actor in my pieces, championing such an important cause. And I got to attend the Oscars.

MARTIN KATZ: Listening to her brings back old memories. I never thought I’d call myself this, but I think I’m the old dog here. I’ve been on the red carpet for over 25 years, longer than anybody except perhaps [Harry] Winston.

You first lent jewelry to Sharon Stone for the 1991 premiere of “Basic Instinct.” But you were initially reluctant. Why?

MR. KATZ: I was a budding private jeweler just moving into my own designs. I showed her a few items. The next day I get a call saying Sharon wants to wear the collar and the bracelet that you showed her. I said: “Whoa, whoa. I thought she wanted to buy these things.” I wasn’t interested in loaning them. She’ll look great, but I’ll take the risk if she loses or breaks something.

But you gave in when Ms. Stone agreed to credit you in the printed press she did to promote the movie.

MR. KATZ: It turned out to be the biggest movie in the world. My name was everywhere. For the next five, six years, I monopolized the red carpet. Once the stylists got involved, they wanted to control things. That’s how things started to spin out.

MR. KWIAT: Martin hits on a really important point: The most exciting times on the red carpet are when there’s a really authentic, creative moment. The first meaningful moment Fred Leighton had on the red carpet was when Miuccia Prada called and asked to borrow an opal choker for Nicole Kidman in 1996. It was the first time Nicole had walked as a budding style icon, and the attention that came with that placement made it clear how exciting and important this could be for building the name and the brand.

MR. KATZ: It was a heartfelt collaboration. This wasn’t a stylist with their hand out, a celebrity asking for a paid endorsement. This was real. That’s what’s missing from the red carpet today. I remember the year “Million Dollar Baby” was nominated [2005]. That was the first time I realized people were paying celebrities. I was at a party at the Beverly Hills Hotel, pre-Oscars, and a gentleman who was running Asprey at the time said to me, “So who are you paying this year to wear your jewelry to the Oscars?” And I laughed. I thought it was a big joke, and then I realized he was completely serious.

It’s rare for a brand to acknowledge these kinds of deals. But I’ve read about payments that have reached $1 million.

MR. KATZ: For big international brands that have stores everywhere, paid endorsements can make a lot of sense. They’re spending a lot of advertising money. And they have doors in every major country, so when somebody sees it, they can walk in. For me to pay those exorbitant amounts makes zero sense.

For smaller brands, what is the return? Does it translate to sales?

MR. KWIAT: The return is brand awareness, first and foremost. While it can be hard to specifically point to the value it brings in dollar terms, it’s unquestionably been important to the growth of the business.

Do any of you ever feel pressured to give pieces away?

MS. PÉAN: We’d go bankrupt if we had to give pieces away or pay celebrities, so it’s really a much more organic relationship. Kerry Washington has been really supportive — when she started working on “Scandal,” she told the costume designer she really loved my work and that she’d really like to write us into the show. They asked for a ring, and the ring has traveled through all the many seasons of “Scandal” — it was the ring the president gave her.

Did they buy the ring?

MS. PÉAN: They did.

What kind of pieces work on the red carpet? Can we assume the bigger the better?

MS. SHERGALIS: It’s a real mix. Often when the dress is more ornate, they want something simpler, like a big oversized stud, a cocktail ring or a cluster of line bracelets. This past season we saw a number of chokers and close-to-the-collar necklaces. We’ve also seen the emergence of ear climbers, ear cuffs. But I don’t think bigger is always better.

MR. KATZ: I actually think they went too big this year. Like the stones Charlize wore to the Oscars — those earrings wore her. I always say, you must match the personality of the celebrity to the jewelry you use with them. When some of these houses are all about the shock value of jewels so big, it’s really not that pretty.

MR. KWIAT: And it calls attention to the fact that “These are not my jewels!” The best placements on the red carpet are the ones that seem like the person could own those pieces.

Monique, do you feel you’re sought out because of your brand’s sustainable ethos?

MS. PÉAN: The actress or actor has to appreciate the design or aesthetic. If they’re focused on sustainability or philanthropy, that’s an added benefit. Last year at the Golden Globes, Taylor Schilling wore my dinosaur-bone ring with recycled gold, and that was really exciting, because that’s not normally what you wear to those events. But she also wore a black sequin custom suit from Thakoon that really went against the grain for the Golden Globes.

If you could single out one red carpet look as your favorite of all time, what would it be?

MS. SHERGALIS: When Nicole Kidman wore the diamond sautoir to the Oscars in 2008. It was a huge piece, but Nicole being Nicole, she really wore it. And on the flip side, working with Janelle Monáe this year, that really fun dress with a fistful of diamond rings. It was so whimsical.

MR. KATZ: It’s a little like saying what’s the absolute best restaurant there is? Certainly, Nicole Kidman [at the 1997 Oscars] in that green Galliano for Dior dress wearing my vintage Mughal jewelry.

MR. KWIAT: When Lupita Nyong’o went to the Oscars [in 2014], it was the culmination of an entire season that we’d worked with her, from the Golden Globes to the SAGs [Screen Actors Guild awards]. It was a lot of pressure, and we were working with her stylist, trying to create something that hadn’t yet been done. She saw this gold and diamond headband, a piece we make at Fred Leighton, and said, “I like that.” By the end of the night, the headband had its own Twitter account.

Are pieces like that more or less salable after being splashed across the media?

MR. KATZ: I once had a client who called about a necklace, probably 15 years ago, and it had just been on somebody on the red carpet. I don’t remember who it was but it was a big one, so I assumed he saw it on this person, and I said, “Oh, that was the necklace that was on so-and-so.” And there was a big pause. And he said, “Well, that’s O.K., I’ll buy it anyway.”

MS. SHERGALIS: We send jewelry that’s been worn on the red carpet to some of our jewelers, and that provides a lot of value. Their clients can see the big piece that was worn on the red carpet and then translate that down to something wearable.

Over the last five, six years, as Instagram has become a force, how have things changed?

MR. KWIAT: The feedback loop is instant. The client sees it, he posts it.

MR. KATZ: If the celebrity is kind enough to tag you, then your followers go through the roof. More often than not, they forget.

MR. KWIAT: That’s where the stylist comes in handy.

MR. KATZ: It got tired. This rote question and answer: “Who are you wearing?” It became very forced and tired, and you can feel that. If you roll back the tapes 15, 20 years ago, back then when it was still fresh, and you look at the thrill when the celebrity said: “Look what I’m wearing! Can you believe I’m getting to wear this?” That’s when it was fun.

MS. SHERGALIS: That’s what social media can provide in a way. Maybe there are those formal moments on the red carpet but then before, when they’re getting dressed, they’ll have the jewelry at home and they can post it on social media in their own way. Kate Hudson wore these 20-carat Exceptional diamond earrings a couple years ago, and she took a picture of herself in bed the next morning after the award show wearing the diamonds. And she was like, “Couldn’t take them off last night.”

MR. KWIAT: In some ways, that’s as good a moment as the actual red carpet.

I can’t help but wonder what the red carpet might look like a decade from now.

MS. PÉAN: Hopefully, we’ll continue to see actors and actresses letting their true style come through.

MS. SHERGALIS: We’re seeing a lot more pay-to-play, but I also think we’re seeing actresses choose small independent designers that align with their own values. That’s when the red carpet starts to mean something more.

MR. KATZ: I think where jewelry houses like ourselves are best suited in the market now, given the pay-to-play of the big carpets, are the smaller carpets where the celebrity is more comfortable and the stylist is more comfortable to choose something they really want to wear. Because when it comes to the Oscars red carpet, there’s too much at stake for the international houses not to monopolize that stage. But you can’t blame the celebs. It’s a lot of money being thrown at them.