The 102 Most Stylish Gifts to Give This Holiday Season
This year, give the gift of good taste
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Many of the styles below can be found on-sale during the Cyber Monday; you can check out a comprehensive breakdown of all the stylish deals we could find here.
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 102 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.
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.
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.
In partnership with Neiman Marcus
A brown suede bomber with a shearling collar is about as idiot-proof as it gets in the jacket department. It exudes timeless, effortless cool, whether paired with jeans and a tee or a more elevated getup (see: Henry Golding’s bomber/turtleneck combo in The Gentlemen). This handsome number from Neiman Marcus is the perfect chocolate-y shade with genuine dyed lamb shearling (increasingly rare these days), and it’s sure to look even better the longer you own it.
Lululemon Always in Motion Boxer 5” 5-Pack
Give the gift of comfort (x5) this holiday season.
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.
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.
Public Rec All Day Every Day Pant
Gift a pair of bottoms he’ll wear all day, every day.
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.
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.
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.
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.
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.
Twillory Non-Iron White Twill Shirt
Every guy needs a dress shirt. Make his life a little easier and get him a good one, like this one from Twillory. A traditional cut, no-iron design, and unique blend means this is one present he doesn’t return.
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.
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.
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.
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.
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.
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.
Levi’s 501 Original Fit Jeans
Maybe you’ve heard of them?
J.Crew Fair Isle Sweater
Tired: gifting holiday sweaters. Wired: gifting holiday sweaters that can be word post-holidays.
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.
Nike Sportswear Club Fleece Sweatpants
Sometimes the most stylish (see: most comfortable) gifts don’t have to be expensive.
Ministry of Supply Velocity Blazer
Every stylish guy needs a stylish blazer.
Bonobos Strech Washed 2.0 Chino Pants
These aren’t just any old chino pants — these are stretch chinos. Bring on the movement!
Western Rise Strongcore Hoodie
Western Rise combines swagger, comfort and performance in a pretty little hooded package.
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.
Myles Apparel Everyday Tee
An InsideHook-approved, durable cotton tee is sometimes the most stylish piece in the arsenal (think James Dean).
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.
Patagonia Fjord Flannel Shirt
An eco-conscious and easy-on-the-eyes flannel for the holidays? Gifting doesn’t get much easier than that.
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.
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.
Gap Vintage Soft Hoodie
If you’re going to gift loungewear, make sure it’s soft loungewear.
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.
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.
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.
Carhartt Loose Fit Double Front Work Pant
Double the front fabric, double the fun.
Stylish Statement Gifts To Wow Any Guy:
COS Utility Wool Jacket
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.
Lemaire Silk Shirt
He might have everything, but we bet he doesn’t have a $740 silk shirt.
Brooks Brothers Alpaca Blend Tennis Sweater
For that aspiring tennis star in your life. Or maybe just a guy who wants to stand out.
Rowing Blazers Warm and Wonderful Sheep Scarf
Do everyone a favor and bestow the gift of Princess Diana this holiday season.
Paraboot Michael Shoe
French shoemakers Paraboot are the definition of timeless chic: their Micheal style, a U-shaped dress shoe, instantly elevates any ‘fit.
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.
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.
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.
Todd Snyder Italian Pinstripe Sport Coat
Mama Mia! That’s a good looking blazer!
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.
Buck Mason Full-Grain Suede Rider Jacket
Birkenstock Boston Shearling-Lined Clog
He’s already part of the mulement, so why not help fuel the clog-inspired fire?
Versace Round Medusa Ring
A Medusa-emblaze ring is the definition of stone cold drip, no?
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.
Noah Double Pleat Windowpane Wool Trousers
Big pants for a big dresser.
District Vision Greg Cabin Fleece
Bundle him up in a Santa-red hot fleece this Christmas, with bonus points for subtle District Vision branding.
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.
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.
Get-Up-And-Go Style Gifts:
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.
Vuori Kore Short
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.
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.
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.
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.
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.
California Cowboy High Sierra Flannel Shirt
It’s a shirt! It’s a jacket! It’s the perfect gift!
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.
Cold-weather accessories make for great gifts, and this beanie from Huckberry is no exception.
Topo Designs Heritage Canvas Rover Pack
A stylish backpack to store all their stylish new gifts.
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.
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.
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.
Gramicci Truck Belted Fleece Trousers
The award for best combination of outdoor vibes and indoor sensibilities goes to…
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.
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.
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.
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.
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.
Teva ReEmber Fleece Slipper
They’re like little sleeping bags, but for your feet. What more do we really need to say?
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.
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.
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.
Hunter Insulated Sherpa Shoe
Insulated shoes ready to tackle that 1.5K summit pretty stylish to us, especially if there is sherpa invovled.
Seavees Mammoth Boot
These boots are made for walking.
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.
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.
Rockport “Margin” Oxford Shoe
He’ll happily retire the old office shoe once he opens the Rockport “Margin” Oxford.
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.
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.
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.
UGG Nuemel Chukka Boots
Slippers are a great gift, but get him ones he can wear further than to the end of the driveway.
Vans Calf Hair Classic Slip-On
Skaters are in right now. So is animal-print.
G.H. Bass Weejuns
Loafers are back. G.H. Bass make the O.G. loafers. Any questions?
The Most Stylish Accessories To Stock Stuffings With:
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.
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!
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.
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.”
Mejuri Slim Rectangular Signet Ring
Men can wear rings too, you know. The singlet style is a perfect one; casual, but refined.
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.
Calvin Klein 3-Pack Cotton Boxer Briefs
Stocking stuffers don’t have to be throw-away gifts; just ask Mr. Calvin Klien.
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.”
UO Waffle Knit Beanie
A good beanie is a perfect stocking stuffer, and UO’s quality-to-cost ratio is unbeatable.
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.
Q Timex Reissue 38mm Stainless Steel Bracelet Watch
A watch you can trust will be a hit, from a watchmaker you can trust.
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.
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