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30 Timeless Style Upgrades Dad Will Love

After all, there's no time like the present.

Stop us if we're wrong. Your dad is more likely to say something along the lines of "I've had this watch for 35 years" than "Kid, I love how distressed your denim is." That's because, when it comes to getting dressed, dads operate by one simple rule: style trumps fashion. And style comes not from what's en vogue but from what looks great, all day, every day, every decade.

You know: chronograph watches, white button-downs, navy blazers, Oxford lace-ups. These are the style staples that transcend generations. And it's why your dad—a guy who's seen more generations than you—seems to stock his closet with them. He's figured out what works. No reason to change course now.

Still, that doesn't mean he can't use an upgrade here or there. And now that Father's Day is around the corner, you have a golden opportunity to introduce him to something different—without forcing him outside of his comfort zone. Think: button-down shirts that prevent sweating, or a bag that does both work and play, or a Swiss Army knife that's actually cool. Herein, we've cobbled together 30 timeless style upgrades your old man will want to show off. The only thing you'll have to worry about is the wrapping paper.

A timeless timepiece

tissot chrono xl

Tissot Chrono XL Classic

$375; buy now at

There's a reason the chronograph has permeated through time as a menswear essential. And there are many more reasons why Tissot's Chrono XL is as timeless as a chronograph can get. With commanding size (45mm) and a deep blue face not unlike the night sky—not to mention clean, unfussy numerals and elegant hands—anyone wearing this veritable piece of art is sure to get some compliments.

A double-breasted blazer

brunello cucinelli jacket

Traditional Hopsack Sport Jacket, by Brunello Cucinelli

$2,875; buy now at

A double-breasted blazer brings captain-level confidence to the tried-and-true navy blazer. And while many DBBs can look a little too much the part (you know: like a sea captain), this lightweight, linen-silk offering, from the suiting maestros at Brunello Cucinelli, is elegant enough to seamlessly slide into any decades-established wardrobe.

A pair of iconic frames

oliver people shades gregory peck

Gregory Peck 47 Sun, by Oliver Peoples

$365; buy now at

Fact: every father on the planet idolizes Atticus Finch, the arbiter of justice from To Kill A Mockingbird. Now, thanks to the folks at Oliver Peoples, your dad can cop Finch's look; these sunglasses are styled after Gregory Peck's immortalized portrayal of the character. He'll never need another pair of shades again.

An indestructible duffel

coach explorer bag

Explorer Bag 52, by Coach

$895; buy now at

Replace your dad's trusty and dusty duffel by gifting him an next-level leather option. This sumptuous beauty from Coach offers more than mere looks: It's loaded with pockets and constructed from a burnished calfskin that's all but bulletproof.

A cashmere hoodie

Polo Ralph Lauren Washable Cashmere Zip Hoodie

Cashmere Zip Hoodie, by Polo Ralph Lauren

$295; buy now at

Every guy has a hoodie. Few guys have a cashmere hoodie. Polo Ralph Lauren's full-zip is so luxuriously soft you'll likely end up leaving the store with two—one for pops, and one for you.

A better golf shirt

mack weldon INTREPID tee

Intrepid, by Mack Weldon

$78; buy now at

Mack Weldon's Intrepid polo is infused with odor-fighting threads. It's the perfect shirt for 18 holes on a balmy day.

A treasurable set of collar stays

turnball and asser Set-Of-Two Mother-Of-Pearl Collar Stays

Collar stays, by Turnbull & Asser

$75; buy now at

Frumpy collars are the bane of every guy's existence. Make sure your dad never has to deal with them again by gifting a pair of collar stays that will stand the test of time, like this beautiful mother-of-pearl pair. Since they're made by the shirt savants at Turnbull & Asser—folks who would never want a collar to droop—you can rest assured they'll do the trick.

A more appropriate pair of jeans

fit 2 in earl rag and bone jeans

Fit 2, by Rag & Bone

$250; buy now at

We're all well acquainted with "dad jeans." (For visual reference: Jerry Seinfeld, circa any year.) Ease your dad away from these insipid, boxy abominations by offering him a slimmer fit that still retains the same traditional, pre-washed blue look, like the Fit 2, from Rag & Bone.

A spy-grade umbrella

oak Brigg Collection umbrella

Brigg Collection, by Swaine Adeney Brigg

$454; buy now at

Forget the convenience store options; the umbrella can indeed reach heirloom status. Just look at the offerings from Swaine Adeney Brigg. (If you're a fan of the Kingsman franchise, you're already familiar with their work.) Hand-carved from English oak and polished to a blinding sheen, this is one umbrella dad won't forget on the tour bus. Also, for an extra $25 per letter, you can even get it engraved.

A double monk-strap shoe

Bankston Cap Toe Double Strap Monk Shoe TO BOOT NEW YORK

Bankston, by To Boot New York

$395; buy now at

Whether your dad's a disciple of the cap-toe or the brogue, it's a good bet he's been wearing Oxfords of some kind for as long as he can remember. Introduce him to something with a little more flair: a double monk-strap. For best results, get him a minimalist option, like this jet black cap-toe pair, from To Boot New York.

An everlasting work bag

BLEU DE CHAUFFE Remix Leather-Trimmed Canvas Briefcase

Remix, by Bleu de Chauffe

$400; buy now at

Brass trimmings, distressed leather straps, and Cordova canvas—a blemish-repelling twist on traditional canvas—make for one head-turning gift. The personalized touch—every bag from Bleu de Chauffe comes with a signed-and-dated label from the craftsman—makes for an unforgettable one.

A rockstar-worthy jacket


Ellison Bomber, by All Saints

$525; buy now at

If your dad likes rock 'n' roll… Who are we kidding? Of course your dad likes rock 'n' roll. Unleash his inner Jagger by getting him a leather jacket. But exercise some restraint: get a bomber. It's a timeless style that men of any age can pull off without looking like a wannabe rocker—or worse: a retired one.

A waterproof watch

tissot seastar 1000

Seastar 1000 Gent, by Tissot

$695; buy now at

The Seastar 1000 Gent takes "waterproof" to a whole new level, literally. This beast can withstand water pressures up to 1,000 feet, and does so with jaw-dropping looks: a steely gradient-blue face, a translucent case back, and hands that light up in the depths—whether the ocean or the night. In other words, it handles high-pressure situations on land and sea with equal aplomb.

Slimmed-down neckwear

hermes Chevron tie

Chevron, by Hermès

$180; buy now at

We'd bet good money that your old man can shave an inch off every tie in his repertoire. So get him started on a neckwear collection reboot. Your best bet is something along the lines of Hermès' Chevron. It's slimmer (2.76 inches) and hipper, yet still retains the '80s power-tie sheen that's currently dominating his closet.

A tie-clip

LANVIN Ruthenium-Plated Tie Clip

Ruthenium-plated tie clip, by Lanvin

$135; buy now at

While you're revitalizing his tie rack, infuse some Mad Men-level style by gifting him a tie clip. Lanvin's burnished gunmetal piece is muted and functional, and the size (2.36 inches) will fit just fine with any tie in his collection—new or old.

A bunch of pocket squares


Anything by The Tie Bar

$15 each; buy now at

Finalize off your dad's torso style transformation with a few pocket squares. And for balmy days where neckwear might be cast aside, a pocket square is a surefire way to convey gravitas and status. The pocket square collection at The Tie Bar is nearly 1,000 deep, and you'll find everything from paisley to plaid to polka-dotted to plain. Go wild.

A sweat-proof dress shirt

Apollo 3 Dress Shirt

Apollo 3, by Ministry of Supply

$115; buy now at

Designed by folks from MIT (in other words: the science checks out), the shirts from Ministry of Supply are practically programmed to eliminate sweat. According to the company, the fabric breathes a whopping 19 times better than traditional cotton. What's more, it's designed to de-wrinkle automatically after coming in contact with body heat. Good-bye, ironing.

A cleaner boot


Liverpool, by Allen Edmonds

$495; buy now at

Yes, Chelsea boots tend to be the domain of Instagram models and other younger, fashion-minded men. But the clean-lined, elegant silhouette and supple yet indestructible leather of the Liverpool make this one Chelsea boot your dad can effortlessly pull off—and will for years to come.

A suave rucksack

Burberry The Large Rucksack in Vintage Check

The Large Rucksack, by Burberry

$1,650; buy now at

Between the meticulous stitching, burnished hardware, hand-painted leather, and that timeless Burberry check, one thing's for sure: this bag is more a piece of art than it is a rucksack. Oh, and it also has a ton of pockets.

A permanent pen

Meisterstück Platinum-Coated 149 Fountain Pen

Meisterstück 149, by Montblanc

$985; buy now at

A keen look at the tip of Montblanc's Meisterstück will reveal, amidst the platinum and gold, an intricately engraved work of art. But it's a generation-spanning invincibility that makes this handcrafted instrument such a delectable item: thanks to a layer of rhodium, the point will never dull, meaning it'll keep a spot in your dad's pocket ad infinitum.

A Pulitzer-level flask

Leather-Wrapped Flask

Leather-wrapped flask, by Moore & Giles

$105; buy now at

Gifting a flask is like falling off a balance beam. You'll land on one side or the other: trashy (one fit for the town drunk) or classy-as-hell (one fit for Truman Capote). Be sure you fall on the Capote side by picking out a leather-clad option. Bonus points if you pick one with an elegantly worn-in look, like this stainless flask, from the leather maestros at Moore & Giles.

A white t-shirt that stays white


Luxe Lotus Jersey Crew, by James Perse

$165; buy now at

How many plain white tees do you think your dad has burned through over the years? (Our guess: somewhere squarely in the triple digits.) Make it so he never again has to waste time or money on picking up yet another by gifting him a suvin cotton tee, like this classic cut from James Perse. It's among the most luxurious cotton varieties on the planet and maintains the new-shirt luster far longer than the traditional Hanes three-pack.

A pair of red soles

Christian Louboutin- Cousin Charles Flat

Cousin Charles Flat, by Christian Louboutin

$995; buy now at

By gifting your dad a pair of red-soled Oxfords, you're giving him more than an über-louche dress shoe. You're giving him a lifetime seat on the style pantheon. How many guys, after all, do you see rocking the iconic red sole?

A pair of upscale no-show socks

Brooks Brothers Loafer Socks-Three Pack

Loafer socks, by Brooks Brothers

$25 for set of 3; buy now at

Few things offend the olfactory nerves so much as a sweat-soaked shoe—especially if that shoe's been around the block. Still, few of life's pleasures match going sock-free in the summer. Give your dad the best of both worlds by stocking him up with a drawerful of invisible socks.

A blue wristwatch

Chemin Des Tourelles, by Tissot

$795; buy now at

A "timeless" watch doesn't have to be steel or black or brown. Just look at the Chemin Des Tourelles, from Tissot. With elegant proportions and stunning stainless hardware, done up all over in a decadent midnight blue, it's the type of watch one might spot at an art gallery opening—either on the most eternally stylish guy, or as one of the exhibits.

Sweats fit for the 21st century

jersey jogger pants ted baker

Window, by Ted Baker

$159; buy now at

You'd be forgiven for assuming, at first glance, that these pants are boardroom-appropriate trousers. Though they're tailored to a tee and even look like well-cut suit pants, look closer, and you'll spot a drawstring waist, extra give, and luxuriously soft jersey fabric—in other words, all the hallmarks of a pair of sweats.

A reversible belt

PRada Saffiano Cuir Leather Reversible Belt

Saffiano Cuir Belt, by Prada

$495; buy now at

Reversible belts get a bad rap. And often, it's for good reason: the leather tends to be cheap, the buckles tend to be flimsy, and owning one in the first is a sartorial copout. Well, Prada's next-level two-tone belt, crafted from hand-tanned Italian leather, happens to fall in precisely zero of those categories.

A museum-grade Swiss army knife

Swiss Army Knife with Black Onyx in Silver $450

Swiss Army Knife, by David Yurman

From $450; buy now at

For Father's Day, go for gold—or, rather, pietersite. David Yurman's top-in-class gadget is adorned with the rare mineral, elevating the artistry of your standard Swiss Army knife without sacrificing any of the functionality.

A tote

ohare soft shopper

OHare, by Want Les Essentiels

$895; buy now at

Messengers and briefs do the trick for the 9-to-5. Backpacks and duffels cut it on weekend getaways. But there's a middle ground out there that can do it all: a tote. And if you get a luxurious one—like the minimalist, deep-pocketed Ohare, from Want Les Essentiels—there stands a good chance of dad actually using it all the time.

Cufflinks, with a twist

golf and tee Cufflinks

Golf Ball and Tee, by Paul Smith

$108; buy now at

When all else fails, you can always just pick up the most classic Father's Day gift of them all: cufflinks. Instead of opting for a standard boardroom-worthy pair, though, go for something with extra oomph. These golf-ball-and-tee links convey the level of earned nonchalance most dads carry with them like an aura—on the green or off.

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Ari Notis
Ari is an editor specializing in news and lifestyle. Read more
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