An Everyman’s Guide to Wearing a Necklace

Every product was carefully curated by an Esquire editor. We may earn a commission from these links. Here’s how we test products and why you should trust us.Prevaut/Salty Dagger/Peyote Bird5 min readMen’s jewelry, I’ve learned, can be a slippery slope. I’ve been a watch guy since elementary school, if we’re generous enough to count a dual-sided compass/watch on a carabiner as a watch. In college I added a bracelet. I’ve been a ring guy for over ten years, thanks mostly to being married and partially to getting lunch drunk in Albuquerque, going ring shopping for my wife, and finding a sterling silver bear signet ring that I’ve worn non-stop since. I’ve had an earring for two years, thanks to a quick weekend in Miami and a well-timed Harrison Ford interview clip crossing my algorithm about getting his ear pierced in a Claire's.Recently, I’ve been curious about my personal final frontier of men’s jewelry—the necklace. The other listings above are all fairly low entry points, safe experiments in the world of men’s jewelry. The earring may be the exception, but this is 2026; one small silver hoop isn’t that daring, even in the Midwest. A necklace has never really been my thing. I haven’t felt the pull. That is, until this year.For an unrelated project, I was breaking down some of the signature stylistic calling cards of Robert Redford. And there it was, across paparazzi pictures and movie stills and in memoriam roundups. In almost every photo, Redford has some kind of necklace, usually peeking from a precariously unbuttoned western shirt.Bettmann//Getty ImagesFurther study of what we can safely call Hollywood’s golden age of off-duty style shows the same: McQueen and Newman and their contemporaries, swanning around on and off-film, always wearing some sort of necklace or chain or pendant.This is, of course, a common trap: to look at a famously handsome Hollywood star and think, yeah, all that’s separating me from THAT is a necklace. And sure, a good cheekbone and clavicle will get you pretty far in life. There’s no magic amulet here, nothing that will shazam you into leading-man looks. But there are a few lessons on styling from guys whose literal job it was to present themselves favorably to the world. And a few lessons on what necklaces to choose to help get there.So, I put my professional online shopping style writing gig into overdrive, going deep into the Getty Images archives and confusing Google’s settings by repeatedly searching “Insert Hollywood Icon + shirtless” to glean some jewelry 101 tips from the professionals.Start SimpleInstagram and (theoretically, since I don’t indulge) TikTok are full of maximalizing style trend chasers. Why wear one necklace when you can wear four? Why two rings when each finger could have two rings on it? Why dip your toes in the water when you can cannonball into the deep end? And sure, there’s some je ne sais quoi about just committing to something fully and completely out of the gate. But there’s also a lot of tryhard to it.We’re channeling a more reserved, less #sponsoredpost era of dressing here that cares less about link clicks and more about how things look in the real world. So start simple and start with a chain. My favorite, and currently on daily rotation, is the Curb Chain from LA-based Bloedstone. Mine is sterling silver and in the inch length, which hits closer to the sternum than the neck. That’s the prescribed Hollywood A-lister way to wear it, but chart your own path if you want to. Miansai has a thicker 2mm Cuban chain that’s great too. And while we’re covering the “m’s” Mejuri has one too. To my slight surprise, my home state watchmaker Shinola makes one, and less surprisingly so, Esquire-approved David Yurman has this giant one featuring a marketing campaign with Michael B Jordan, who is picking up McQueen’s (and subsequently Broznan’s) torch by adapting The Thomas Crown Affair.There’s a whole vocabulary on link types and thickness and clasps out there. Don’t worry about that for now. Find something that calls to you and click add to cart. We’re starting slowly here.Parting note. There are a lot of chains worn over T-shirts these days. To each their own, but the leading man's move is to keep it under your shirt. If you want to show it off, just ditch the buttons.Then Mix It UpA chain is simple, and sure, the greats wore them. But more often than not, they had something dangling from that chain. Medallion, pendant, a bottle opener in “Cool Hand Luke.” McQueen was often photographed, including in the pages of Esquire, wearing a St. Christopher Medallion. Patron saint of travelers, St. Christopher medallions are having a bit of a cultural resurgence, partially because of their traditional association as a good luck charm for travelers. There are some fun enamel ones on eBay, including these surfing-specific ones. Every once in a while, Nashville-based Americana experts Imogene + Willie will pull together a vintage edit of St. Christopher medallions that always sell out in ~24 hours. Speaking of Nashville, if you’re going to go new, go with Yearly Co. The gold jewelry experts have a 14K version of the iconography with a pitch-perfect 24 in chain. I can attest to the quality — I gave my wife the brand’s diamond huggies and she wears them almost every day. As the grandson of the Protestant minister, I steer away from the saints out of genetic loyalty to Luther’s 99 Theses, but I recently picked up this Perseverance medallion from the brand, inspired by a vintage signet ring. It scratches the McQueen itch with flying colors.Secondhand gold is also an option. Alloy Market recently came onto my radar, and I’m browsing it daily for myself and gifts for my wife. They’ve got a small but mighty collection of certified men’s items with pendants and medallions you can mix and match. All of the quality without any of the markup.Don’t limit yourself to just a medallion, though. Get a little funky. Redford did for a while with this turquoise number that somehow looked even cooler hitting under the sternum. Shinola’s got an option there too. Bali-based Salty Dagger has an Odysseus-approved Greek mythology piece. And why not try a locket, like this one from Pattaraphan. Miansai has a great pendant. Get fancy with the Prevaut diamond ring deal. When in doubt, steal from the girls. I got this With Clarity birthstone necklace for my wife that I might take a swing at myself.From the abbreviated/slightly bastardized Shakespeare: “all the world’s a stage and one man in his time plays many parts.” Jewelry can feel like a risk, even if you’re following some sort of contrived guide to styling and buying it. Sometimes we pretend until we’re comfortable actually being. Redford and McQueen and company were actors; pretending was their legacy, and they were good at it. Take a leaf from their book and get dressed for the curtain call.