August 17, 2022

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The 101 Most Stylish Gifts to Give This Holiday Season

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Nota bene: If you buy through the links in this article, InsideHook may earn a small share of the profits.

Gifting can be tough when it comes to stylish men; after all, it can seem like they’ve already got their whole wardrobes figured out, and the mass barrage of brands and retailers can feel never ending. If that weren’t enough, this year in particular is tricky, with the shipping deadlines and supply chain delays and general falling apartness of the modern world. The whole confluence of factors makes shopping for that special guy feel daunting, and pointless; perhaps just a gift card this year.

But wait! InsideHook to the rescue, with 101 gifts running the gamut from a much needed sock refresh to a silk shirt so fine it’s hard to believe it’s not fake. We’ve picked out something for everyone, with chic and suave gifts for your kick-flipping nephew, dapper brother-in-law, still learning-how-to-dress boyfriend, or your impossible-to-shop-for husband. Whoever is on your gifting list, rest easy knowing that you’ll find the hottest, trendiest, and otherwise most stylish items below.

a pair of corduroys

L.L. Bean

L.L. Bean Strech Country Corduroy Pants 

L.L. Bean’s Corduroys never go out of style, which is one of many reasons they make such a good gift. And even given their extreme durability, they aren’t going to break the bank.

a 5 pack of briefs

Lululemon

Lululemon Always in Motion Boxer 5” 5-Pack

Give the gift of comfort (x5) this holiday season.

a rust red sweatshirt

Reigning Champ

Reigning Champ Midweight Terry Crewneck

If the phrase “elevated basics” wasn’t already in your vocabulary, just take a look at Reigning Champ’s midweight terry crewneck, and you’ll get an idea. Comfortable and stylish, this is a gift he’ll be ecstatic to receive. 

a handsome silver watch

Seiko

Seiko Japanese Mechanical Automatic Watch 

Undeniably sleek and with an immaculate Japanese make, it’s hard to imagine anyone, watch enthusiast or otherwise, not appreciating this gift. Plus, the two day shipping!

a pair of flannel lined jeans

prAna

PrAna Hillgard Lined Jean

You can never go wrong with flannel-lined jeans, especially ones that skew brawny lumberjack. Toss on a flannel and some boots, and you’ve got yourself a winning winter combination.

a pair of two-toned brown loafers

Blackstock & Weber

Blackstock and Weber The Mason Horse Bit

New kids on the block Blackstock and Weber are crafting some of the hottest footwear money can buy. Their Mason Horse Bit is the definition of perfect sneakerhead upgrade — drenched in rich browns and luxe as hell, these should be on any stylish guy’s wishlist. 

A black carhartt jacket

Carhartt

Relaxed Fit Washed Duck Sherpa-Lined Utility Jacket 

The Sherpa-Lined Utility Jacket is the perfect outerwear refresh for any rough-and-tumble fella. Hefty enough to fight off winter’s bite and very much in style, this jacket rules.

a pair of green fatigue pants

Rhythm

Rhythm Fatigue Pant

Fatigue pants are all the rage, but get him ones that make him look militantly good, rather than ones that make him look like he’s playing dress up. 

a pair of pull on pants

Public Rec

Public Rec All Day Every Day Pant 

Gift a pair of bottoms he’ll wear all day, every day. 

a pair of green and black technical shoes

Salomon

Salomon X6-Trail Runner 

French trail shoe makers Salomon have broken into “hype shoe” territory, and we’re glad they did. The X-6 Trail Runner is a perfect mix of easy-on-the-eyes and easy-on-the-jog. 

a gray jogger

Rhone

Rhone Luxe Knit Jogger

Rhone’s athleisure doesn’t just look great, it feels amazing, too. These knit joggers have the perfect tapper silhouette for some holiday lounging.

a pair of silk PJs

Lahgo

Lahgo Washable Silk Button Up Set

Silk PJs might not be on his wish list, but that doesn’t mean that a luxurious addition to his nighttime routine wouldn’t be a welcome one. Sleepwear brands Lagho’s trademark set is so supple he’ll never want to take it off. 

a waffle crew in navy

Faherty

Faherty Legend Waffle Crew 

The waffle-knit is a go-to winter style, and Faherty makes one of the best around. Easy to layer and handsome on it’s own, the Legend Crew is a must-have. 

a pair of white sneakers

Reebok

Reebok Club C Sneaker

Pound for pound, the Reebok Club C might just be the best white sneaker money can buy. Versatile and sleek, it’s a perfect introduction gift to a budding stylish wardrobe.

a horse emblazoned sweater

Brooks Brothers

Brooks Brothers Valley Ranch Handknit Horse Motif Sweater Jacket

For that aspiring cowboy in your life. Or maybe just a guy who wants to stand out. 

Richer Poorer Recycled Fleece Raglan Sweatshirt

Workout-ready? Absolutely. Hangout-worthy? Most certainly. However he chooses to wear the short-sleeve fleece sweatshirt from Richer Poorer, there’s no question he’ll be comfy as all get out.

a handsome chukka boot

Astroflex

Astorflex Greenflex

Chukkas are the holy grail of office shoes: dressy enough to wear to work but comfortable and laid back enough to wear to happy hour. The Astorflex Greenflex is a great example of how good the gift of Chukka can be. 

a pair of wool socks

CHUP

CHUP Musik Socks 

Even a stylish guy needs new boot socks every now and then, so why not get him ones he’ll enjoy? Ultra-comfy and perfectly festive, CHUP’s basics will also last a lifetime.

a pair of athletic shorts

Vuori

Vuori Kore Short 

Good enough for Harry Styles, good enough for any man on your gift list.

a sheep graphic scarf

Rowing Blazers

Rowing Blazers Warm and Wonderful Sheep Scarf 

Do yourself a favor and bestow the gift of Princess Diana this holiday season. 

An all white polo

Orlebar Brown

Orlebar Brown Cotton-Terry Polo Shirt

A polo is a tried and true classic in the style department, and Orlebar Brown’s wide-collared, cotton-terry take is the perfect gift, regardless of his country club status.

A bright orange hoodie

Arc’teryx

Arc’teryx Atom LT Insulated Hoodie 

Arc’teryx makes arguably the hottest weatherproof apparel currently on the market. The Atom LT in a bright color (we suggest an orange, yellow, or red) will beat wintery conditions with stylish aplomb. 

a crisp white dress shirt

Land’s End

Land’s End Traditional Fit Dress Shirt 

Every guy needs a dress shirt. Make his life a little easier and get him a good one, like this one from Land’s End. A traditional cut, no-iron design, and supima cotton blend means this is one present he doesn’t return.

a knit cardigan

Corridor

Corridor Crochet Grandpa Cardigan 

The hottest gift this season? A cardigan straight out of your grandpa’s sweater. Corridor’s colorful knit is sure to be the coolest thing he’ll receive.

Satisfy Wave Tee

Luxury running brand Satisfy knows how to make a running shirt. Incredibly soft and rendered in a muted lime green, the Wave Tee looks just as good out and about as it does on the track. 

Teva ReEmber Fleece Slipper

They’re like little sleeping bags, but for your feet. What more do we really need to say? 

Nike ACG NRG Smith Summit Belted Nylon Trouser

Nike’s performance outdoors line, All Conditions Gear (ACG) is always on the cutting edge of performance. This season, they’re on the cutting edge of fashion, too. 

a Salomon pink cap

Sporty and Rich

Sporty and Rich Good Health Hat

Maybe he’s sporty. Maybe he’s rich. Maybe he’s both — and even if he’s neither, this is still a fun cap. 

a black faded hoodie

General Admission

General Admission Vista Hoodie 

A good-looking hoodie can be hard to find; luckily, California-based General Admission makes it easy with their Vista Sweatshirt. Sun-faded and fleece-backed, it’s a layer he’ll never want to take off. 

a pair of loose fitting pants

Saturdays NYC

Saturdays NYC George Brushed Cotton Trousers 

With a looser fit and elastic waistband, these stylish trousers will be a smash-hit gift, even after that huge holiday dinner.

a pair of sleek brown Chelsea boots

R.M. Williams

R.M. Williams Gardner Boot

A leather chelsea boot is a stylish man’s wardrobe staple, Aussie-based R.M. Willian’s makes some of the best money can buy.

a brown leather belt

Johnson and Murphy

Johnson and Murphy Baldwin Belt 

A good leather belt is the style gift he didn’t know he needed, and Johnson and Murphy know a thing or two about leather. 

a puffy jacket

The North Face

The North Face 1996  Retro Nuptse Jacket 

Don’t let the cold stymie his ‘fits. The North Face 1996 Nuptse is the retro-inspired colorful puffer he won’t be embarrassed to rock. 

Shirt

California Cowboy

California Cowboy High Sierra Flannel Shirt 

It’s a shirt! It’s a jacket! It’s the perfect gift!

a pair of jeans

Outerknown

Outerknown SEA Jeans

A good pair of jeans is a must-have for any guy, so why not gift one’s that’ll only get better with age? Outerknown’s SEA denim is the straight-legged, classic-indigo denim to rule them all.

a white cable knit vest

Abercrombie & Fitch

Abercrombie Oversized  V-Neck Sweater Vest 

You haven’t heard? The ‘90s are back! This includes the iconic sweater vest. Abercrombie makes a certified-fresh one that’s easy to layer and easier to give.

a beige chino

Flint and Tinder

Flint and Tinder 365 Chino Pant 

A chino for the office and his day off, the versatility of these Flint and Tinder pants is unmatched. 

an oversized shoe

Hoka One One

Hoka One One Clifton Edge Shoe 

The definition of a very big gift, the Clifton Edge is all about pushing it to the max: max cushioning, max stack high, max chunky-sneaker-style.

a gold chain

Maple

Maple Grace Gold-Plated Pendant Necklace 

A chain is extra special if it comes from someone you care about. Also if it’s vaguely inspired by Grace Jones.

a pair of wallabee shoes

Clarks

Clarks Wallabee Shoe

Trust us when we say that these shoes (however odd they may look) are deserving of a spot in any stylish man’s footwear rotation. 

a houndstooth jacket

Todd Snyder

Todd Snyder Italian Pinstripe Sport Coat  

Mama Mia! That’s a good looking blazer! 

a pair of medium wash jeans

Levi’s

Levi’s 501 Original Fit Jeans 

Maybe you’ve heard of them? 

a pair of oxfords

Doc Martens

Doc Martens 1461 Leather Oxfords

For the punk, the preppy, the overdresser — for anyone who has even a single stylish bone in their body, really.

a festive sweater

J.Crew

J.Crew Fair Isle Sweater 

Tired: gifting holiday sweaters. Wired: gifting holiday sweaters that can be word post-holidays. 

a flannel shirt

Pendleton

Pendleton Flannel Board Shirt 

This is what is affectionately referred to as a twofer: that’s two gifts in one, a blanket and a shirt. 

a robe coat type deal

Offhours

OffHours Homecoat

The OffHours Homecoat is exactly what it sounds like — it’s a coat for home. Complete with puffy down ribbing and an appealing color scheme, he’ll be wearing this out in public before you know it. 

a knit blue beanie

Huckberry

Huckberry Beanie 

Cold-weather accessories make for great gifts, and this beanie from Huckberry is no exception.

a waxed jacket

Barbour

Barbour Beaufort Jacket

The classic waxed jacket happens to be a classic stylish gift to impart on those who need the weatherproof protection and understated charm of a heritage make. 

a cream colored long sleeve polo

Lacoste

Lacoste Classic Long Sleeve Pique Polo Shirt

Under a cable-knit or over a turtleneck, the Lacoste marl pique polo is the definition of debonair. 

a leather belt

Tanner Goods

Tanner Goods Standard Belt 

The standard belt is anything but. Handsome and handcrafted, this is one oddly shaped present he won’t mind finding under the tree.

a suede jacket

Buck Mason

Buck Mason Full-Grain Suede Rider Jacket

Every man should have a suede jacket.

a pair of black sweatpants

Nike

Nike Sportswear Club Fleece Sweatpants 

Sometimes the most stylish (see: most comfortable) gifts don’t have to be expensive. 

a shearling lined clog

Birkenstock

Birkenstock Boston Shearling-Lined Clog 

He’s already part of the mulement, so why not help fuel the clog-inspired fire?

a gold ring

Versace

Versace Round Medusa Ring 

A Medusa-emblaze ring is the definition of stone cold drip, no? 

a pair of green chinos

Bonobos

Bonobos Strech Washed 2.0 Chino Pants

These aren’t just any old chino pants — these are stretch chinos. Bring on the movement! 

a grey hoodie

Western Rise

Western Rise Strongcore Hoodie 

Western Rise combines swagger, comfort and performance in a pretty little hooded package. 

a cream colored fleece

Uniqlo

Uniqlo Windproof Fleece Jacket 

Want to windproof their holiday season without the fleecy premium? Uniqlo’s fluffy zip-up is retro-inspired, warm as all get-out and only $50 bucks.

a green and tan colored backpack

Topo Designs

Topo Designs Heritage Canvas Rover Pack 

A stylish backpack to store all their stylish new gifts. 

a U-shaped shoe

Paraboot

Paraboot Michael Shoe

French shoemakers Paraboot are the definition of timeless chic: their Micheal style, a U-shaped dress shoe, instantly elevates any ‘fit.

a black tee shirt

Myles Apparel

Myles Apparel Everyday Tee

An InsideHook-approved, durable cotton tee is sometimes the most stylish piece in the arsenal (think James Dean). 

a pair of blue pants

Tracksmith

Tracksmith Traveler Pants 

Tracksmith doesn’t just make quality running gear, they make really good-looking pants. A trim fit, tab closure and hidden waistband make these pants ones you should be sprinting to give this holiday season. 

a pair of two toned loafer s

G.H. Bass

G.H. Bass Weejuns 

Loafers are back. G.H. Bass make the O.G. loafers. Any questions?

a blue flannel shirt

Patagonia

Patagonia Fjord Flannel Shirt 

An eco-conscious and easy-on-the-eyes flannel for the holidays? Gifting doesn’t get much easier than that.

a navy sweater, embroidered with a bear

Ralph Lauren

Polo Ralph Lauren Bear Sweater

Anything Polo Bear is a great gift, but the Polo Bear on a horse on a sweater? That’s a real winner.

a pair of decorated vans

Vans

Vans Calf Hair Classic Slip-On

Skaters are in right now. So is animal-print. 

a pair fo grey French Terry joggers

Everlane

Everlane French Terry Sweatpants 

Give the gift of loungewear this holiday season; after all, his WFH sweatsuit has probably seen better days, and this one looks a hell of a lot better.

a light blue blazer

Ministry of Supply

Ministry of Supply Velocity Blazer 

Every stylish guy needs a stylish blazer.

a pair of ugg chukka boots

UGG

UGG Nuemel Chukka Boots

Slippers are a great gift, but get him ones he can wear further than to the end of the driveway. 

a green faced, silver watch

Timexx

Q Timex Reissue 38mm Stainless Steel Bracelet Watch

A watch you can trust will be a hit, from a watchmaker you can trust.

a green turtleneck sweater

Banana Republic

Banana Republic Merino Turtleneck

Unsure what to get the dapper gentleman? A turtleneck is always a good guess, and this one from Banana Republic checks all the right boxes.

a pair of black overalls

Dickies

Dickies Overalls

For the younger guy who seemingly has it all, a pair of overalls can be the stylish gift they didn’t know they wanted.  

A pair of white athletic shorts

Ten Thousand

Ten Thousand Interval Short 

Workout shorts that perform in the gym and don’t offend at the post-sesh smoothie outing? That’s a gift worth giving. 

futuristic looking shoes

New Balance

New Balance 327 Sneaker

Snaekerhead on the brain? The loud, chunky, and very-in New Balance 327 is a great choice, and for under $100 bucks. 

a silver bracelet with ID tag

Miansai

Miansai ID Chain Bracelet 

Gifting the Miansai ID Chain Bracelet says a lot of things about you, like: “I care about you. Also, I have outstanding taste.”

a yellow beanie

Urban Outfitters

UO Waffle Knit Beanie

A good beanie is a perfect stocking stuffer, and UO’s quality-to-cost ratio is unbeatable.

a green hoodie

GAP

Gap Vintage Soft Hoodie 

If you’re going to gift loungewear, make sure it’s soft loungewear. 

a pair of wool, grey pleated pants

Noah NY

Noah Double Pleat Windowpane Wool Trousers

Big pants for a big dresser. 

black underwear with a banded waist

Calvin Klein

Calvin Klein 3-Pack Cotton Boxer Briefs 

Stocking stuffers don’t have to be throw-away gifts; just ask Mr. Calvin Klien. 

a navy long sleeve tee

Janji

Janji Runterra Bio Tee

You give the gift of a sporty long-sleeve tee, Janji gives the gift of water (to people who need it most), everyone is happy. 

a tan top jacket that is weatherproof

Columbia

ColumbiaPNW Bugaboo 1986 Interchange Jacket

Columbia doesn’t do things halfway, and neither should you this holiday season. Give the gift that will keep him warm, dry and comfortable. 

a brown leather shoe

Rockport

Rockport “Margin” Oxford Shoe

He’ll happily retire the old office shoe once he opens the Rockport “Margin” Oxford. 

a pair of olive pants

Adsum

Adsum Bank Pant

Adsum’s lowkey Bank Pants are the perfect gift for the to-cool-for-school dude. Roomy, durable, and elastic, they’re great for any and every function.

a pair of white converse

Converse

Converse Chuck 70 

If you’ve got someone in your life who wouldn’t appreciate being given a pair of the most classic sneakers ever made, well, we may need to have a talk.

a grey checked scarf

Ted Baker London

Ted Baker Checked Scarf

Scarves are a safe bet for any gentleman you might need to outfit. This neutral gray checked scarf from Ted Baker goes just as well with a sweater and jeans as it does with a full suit. 

a mutlicolr Tye die fleece

Kapital

Kapital Tie Dye Fleece Sweater

It can feel hard to get a gift that really shows how much you love someone. No need to fear: he’ll read you loud and clear when he opens this immaculately crafted, absolutely popping fleece sweater from Japanese brand Kapital. 

a pair of black fleecy pants

Grammici

Gramicci Truck Belted Fleece Trousers  

The award for best combination of outdoor vibes and indoor sensibilities goes to…

a pair of black loungewear shorts

Nice Laundry

Nice Laundry 6” Pocket Lounge Short

The Nice Laundry 6”  Pocket Lounge Shorts are a great way to subtly imply, “I see that you spend all day on the couch, and I accept you.”

a silver singlet ring

Mejuri

Mejuri Slim Rectangular Signet Ring 

Men can wear rings too, you know. The singlet style is a perfect one; casual, but refined.

a brown cap toed boot

Wolverine

Wolverine 1,000 Mile Cap Toe Boot

And I would walk 500 hundred miles, and I would walk 500 more, just to be the person who got you the Wolverine 1,000 Mile Boots.

a pair of olive green chinos

Olviers

Oliver’s Passage Pant

Slim, sleek, stylish, the Passage Pant by Oliver’s is as versatile as a pair of pants can be. We love the fabric as well as the fit, not to mention the plethora of color options.

a grey silk button up shirt

Lemaire

Lemaire Silk Shirt

He might have everything, but we bet he doesn’t have a $740 silk shirt.

a technical trail shoe

On

On CloudAway Shoe

ON Running’s lifestyle offerings are just as good as their performance wares, and the CloudAway is no exception. Trail-influenced and beautifully streamlined, these would be sure to make his weekly hikes a bit more ‘Gram worthy.

a all black sneaker boot

Adidas

Adidas Terrex Free Hiker 

Rarely has a hiking shoe ever been this … hype? The Terrex Free Hiker from Adidas goes all in on the hot sneaker trend without sacrificing any of the outdoor execution. 

a bright red fleece

District Vision

District Vision Greg Cabin Fleece

Bundle him up in a Santa-red hot fleece this Christmas, with bonus points for subtle District Vision branding. 

three pairs of colored striped socks

American Trench

American Trench Athletic Stripe Silver Socks 

Want to avoid the classic “Aww, socks again” reaction? Spread the American Trench gospel. Spun with bacteria-killing silver filament, these will become his favorite socks in no time.

a striped blue shirt

Alex Mill

Alex Mill Mill-Striped Cotton-Poplin Shirt

A poplin shirt done up in bold blue stripes … it’ll look great now and even better come spring.

a wool blue coat

COS

COS Tailored Wool Coat 

For that sophisticated guy in your life. Or they guy who could stand to look a bit more sophisticated. Either way, this wool coat from COS is a classy affair that’s sustainably crafted, to boot.

a heavy bag tee in cream form Taylor Stitch

Taylor Stitch

Taylor Stitch Heavy Bag Tee 

Despite its name, this Taylor Stitch T-shirt does not look like a heavy bag. Au contraire, it’s probably the best plain white tee we can currently think of, with it’s super-soft weave and drapey fit.

a pair of medium wash jeans

Wrangler

Wrangler Authentic Classic 5-Pocket Relaxed Fit Jeans

Wrangle him up a pair of heritage jeans at a can’t-be-beat price. The Classic 5-Pocket relaxed Jeans fit just how denim should; a little big, a little flared, and a lot of comfortable.

a pair of sturdy black boots on a model

Hunter

Hunter Insulated Leather Commando Boots 

Boots ready to kick that 1.5K summit in the teeth seem pretty stylish to us, especially if they’re handcrafted from genuine leather.