23 Men's Watches That Will Never Go Out of Style
Zero affiliate links, thanks to you. Featuring brands like Seiko, Timex, Bulova, and more—with picks across multiple price ranges.
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WHAT MAKES A timeless watch? Is it the silhouette? The historical lore? The versatility?
My answer is this: A timeless watch is one that’s likely to be just as appealing in 10 years as it is today.
Funny enough, a handful of the watches on this list are based on, or inspired by, watches released in the 1950s, 60s, 70s, 80s, and 90s. Many of them are ironclad in watch community opinion—they are “no brainers,” as enthusiasts say.
Now, just to preface: There is no feature of The Crown on this list. I do this as a challenge (but also as a reality of most financial situations) to intentionally leave out Rolex. And let’s be real, this entire breakdown could be Rolex only if that’s how we wanted to chop things up.
By the end of this story, I hope I’ve shown you some newness, reinforced the greatness of watches you’re familiar with, and given you some “X-factors” to add to your collection.
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Most Reliable Watch: Seiko 5 Sport ($295)
I bought my Seiko 5 Sport this past fall on a whim. I was at Macy’s picking up a tie for the Huckberry holiday party, and I spotted this beauty in the watch case and had to have it. There are tons of colors and styles available in the Seiko 5 Sport. Once you secure the watch, then you can start looking up different straps to mix and match with it.
Specs: Case size: 40mm | Movement: Automatic (Caliber 4R36) | Case material: Stainless steel | Face material: Hardlex | Water resistance: 100m
Best Watch Under $200: Q Timex Continental GMT ($189)
The Q Timex Continental GMT has been featured in FIELD JOURNAL three separate times, and each time it has generated a ton of click share. I love the 1970s airport lounge aesthetic. (Think: Hollywood producer hopping a red-eye with aviators and a martini.) It’s got just enough to stand out, namely the 6 o’clock GMT window and the striking contrast between the silver indices and the navy dial. The best part is it’s under $200.
Specs: Case size: 39mm | Movement: Quartz | Case material: Stainless steel | Face material: Acrylic | Water resistance: 50m
Best Adventure Watch: Shinola Duck Watch ($550)
The Duck Watch seems to be a certified hit from Shinola for 2025, and it’s no wonder why. It’s built like a tank, but available in colors that don’t take themselves too seriously. The skin diver features a sapphire crystal face, C3 SuperLumi-Nova hands and indices, and a deep 200m water resistance. The price? A reasonable $550.
Specs: Case size: 42mm | Movement: Argonite 713 quartz | Case material: Stainless steel | Face material: Sapphire crystal | Water resistance: 200m
The IYKYK Watch: Timex 1995 Intrepid Reissue JFK Jr. (Good Luck)
Timex nailed this 1995 Intrepid Reissue a couple months back, both in the design but also the marketing. Like the image suggests, this watch was a favorite of JFK Jr. for it’s sporty, functional purpose. The case is a massive 45mm. The colors are totally 90s. It’s an unmistakable watch with some unique history to tell. It retailed for well under $400 from what I remember. Now, I’m having trouble finding it even on eBay. Grab one if you can find.
Specs: Case size: 45mm | Movement: Quartz | Case material: Stainless steel | Face material: Acrylic | Water resistance: 50m
Best Small Watch: Q Timex® 1982 Ana-Digi Reissue ($189)
Gold-tone, futuristic, and unapologetically ‘80s, this Ana-Digi Reissue is like a time machine for your wrist. Remember how I mentioned this story is about timeless watches? The fact these tiny gold watches have come back into play proves their validity for being in a watch box. At 33m, this compact piece will get plenty of compliments. Break it out when you want to turn some heads.
Specs: Case size: 33mm | Movement: Quartz | Case material: Stainless steel (gold-tone finish) | Face material: Acrylic | Water resistance: 30m
The Mad Men: Oris Divers Date ($2600)
This is the kind of watch Don Draper would’ve worn on a beach weekend in Big Sur back in the 1960s. The Oris Divers Sixty-Five brings clean, mid-century design into a modern Swiss package—minimal lines, thin bezel, legible dial. It’s technically a dive watch, but it leans dressy and refined, with a nod to the golden age of guy’s dressing up.
Specs: Case size: 40mm | Movement: Automatic (Oris 733, based on Sellita SW200-1)
Case material: Stainless steel | Face material: Domed sapphire crystal | Water resistance: 100m
Best Watch Under $500: Hamilton Field Khaki Quartz ($425)
You could make a case that the Hamilton Khaki is the best watch to start a watch collection. It’s that good. The Khaki has a history reaching back as far as WWII, where it became a field watch American soldiers trusted. Some purists might knock for not buying the more expensive mechanical Khaki, but this quartz model does just fine for everyday wear and sits at a much more desirable sub-$500 price.
Specs: Case size: 38mm | Movement: Quartz | Case material: Stainless steel | Face material: Sapphire crystal | Water resistance: 50m
The Search & Rescue: Marathon OSAR-D ($1800)
Originally made for Canadian Search and Rescue technicians (SAR), the Marathon SAR-D is a real-deal government-issue tool watch. It’s heavy-duty in every way: thick case, cyclops date, chunky bezel, and full lume hour markers that glow like a glow worm. But even with all ruggedness, it still wears surprisingly well for everyday use—military serious without being obnoxious.
Specs: Case size: 41mm | Movement: Automatic (Sellita SW200) | Case material: Stainless steel | Face material: Sapphire crystal | Water resistance: 300m
The Aussie Cowboy: Alpina Heritage Carrée ($2139)
First made over a 100 years ago, I pin the Alpina Heritage Carrée as “Australian outback meets art deco.” The strap is made from ostrich leather (something that’s rarely seen on watch straps). The watch itself has a rugged elegance about it that keeps it from veering too dressy. It’s a dress watch sure to gain compliments every time you wear it.
Specs: Case size: 32.5mm x 39mm | Movement: Automatic (AL-530) | Case material: Stainless steel | Face material: Sapphire crystal | Water resistance: 30m
The Fun Dive Watch: Zodiac Super Sea Wolf ($1395)
The Zodiac Super Sea Wolf is proof that dive watches don’t have to be boring. Inspired by skin divers of the 1960s, it brings bright, playful color combos and modern reliability to the mix—all without tipping gimmicky. My two other favorite features include the rubber strap and the Swiss-made movement.
Specs: Case size: 40mm | Movement: Automatic (STP 1-11) | Case material: Stainless steel | Face material: Sapphire crystal | Water resistance: 200m
Best Chronograph Under $250: Timex Q Timex Chronograph ($219)
Another hit, this sub-$250 Timex brings a vintage swagger other chronographs of this price don’t have. It reaches back tot he era of 1970s motorsports and café racing, with a balanced dial and coffee color combo (blacks, browns, and creams). This is a crowd-pleaser for sure.
Specs: Case size: 40mm | Movement: Quartz | Case material: Stainless steel | Face material: Acrylic | Water resistance: 50m
The Sleeper Watch: Bulova Oceanographer GMT ($1450)
Another style the exudes the style and energy of the 1960s, this Oceanographer GMT is a watch your friends and peers won’t ever see coming. The rose-gold case combines with unique silhouette blends between dressy and rugged. It’s far from a gimmick though, packing features like a 200m water resistance, a GMT hand, and a date window.
Specs: Case size: 41mm | Movement: Automatic (Miyota 9075 GMT) | Case material: Stainless steel (rose gold-tone finish) | Face material: Sapphire crystal | Water resistance: 200m
The Toughest Collab Watch: Huckberry x Citizen Promaster Tough ($525)
You can’t go wrong with a Citizen Promaster Tough. This specific collab between my company and the Japanese watchmaker is super versatile in styling. The green dial mixed with the white hands and hallowed out indices and numbers can’t be found on any other Citizen Promaster Tough. At under $600, you get a Super Titanium™ case, EcoDrive movement, and a water-resistance to 200m. Oh, and you get a sweet custom case with a leather watch holder.
Specs: Case size: 42mm | Movement: Eco-Drive solar quartz | Case material: Super Titanium™ | Face material: Mineral crystal | Water resistance: 200m
The American Handbuilt Icon: Weiss Watch Co. Orange Dial Field Watch ($2700)
There aren’t many makers building watches by hand in the U.S., but Weiss Watch Co. is the exception. I love their Field Watch, specifically the limited edition colors like this Tennessee Orange Dial Field Watch. Bright and bold without being flashy, the orange dial adds just enough personality to the otherwise rugged design. The case is machined from stainless steel in Los Angeles, and inside is a manually wound movement assembled and finished by Cameron Weiss himself. A seriously good add to the collection that’s going to never go out of style.
Specs: Case size: 42mm | Movement: Manual-wind (Weiss Caliber 1003) | Case material: Stainless steel | Face material: Sapphire crystal | Water resistance: 100m
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