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Shopping for the fellas? Objectively difficult. Shopping for a man who knows his Thom Browne from his Tom Ford? Even if you consider yourself something of a tastemaker, you’re looking at a nigh impossible task…without some help from your favorite trend-spotting, wardrobe advice-spewing, menswear-centric publication, that is.
InsideHook is here to rescue your worldly image (and the holidays) with a comprehensive list of the best gifts for stylish men, running the gamut from twisty mushroom cardigans to the one rugged waxed jacket to rule them all. There are gifts for every kind of guy you might know: your dapper brother-in-law, TikToker nephew, still-learning-how-to-dress boyfriend or want-for-nothing husband. And there’s something there for you too, chief — go ahead and splash out. You deserve it.
As the foremost authority on all things abstractly cool (read: guys who follow Chris Black and spend a bit too much time hunting for #menswear) you can trust that our cohort of tasty selects will earn you more brownie points than whatever the creatine-snorting, Chat GPT-fueled competition might be shilling. Whoever is on your gifting list, rest easy knowing that you’ll find the hottest, trendiest and otherwise most stylish items below.
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The Best Gifts for Stylish Men to Give This Holiday Season
Our Top Gifts
Billy Reid Herringbone Astor Coat
Every guy shown own a grown-up jacket. The Astor Coat from Billy Reid is just that — it can be worn over a suit or dressed down with a hoodie.
Buck Mason Seastack Wool Tweed Cable Crew
What’s better than a cozy cable-knit? One woven out of a soft, slubby Seastack wool and designed in the image of classic ’60s ski sweaters.
The Best Apparel Gifts
Alex Mill x J.Press Shaggy Dog Crew
The sweater of the season, in the color of the season? Uh, yeah, I think he’s gonna like it.
Imogene + Willie Henry Black Stone
Nashville-based Imogene + Willie is the latest in a long and historic line of American denim purveyors, and their 13-oz Japanese selvage denim Henry Black Stone jeans live up to the standard.
The Best Footwear Gifts
UGG Classic Ultra Mini Leather Regen
As it turns out, he can and should wear UGGs everywhere. This is your sign to gift him a new (premium leather) pair.
Nike T90 SP Sneakers
After a few years of Adidas domination, Nike’s reintroduction of the T90, a beloved mid-aughts soccer silo, couldn’t have come at a better time. An version of the Y2k model will be joyfully received, but this high-shine “Black/Metallic Silver” colorway is particularly footy-coded.
The Best Grooming Gifts
Aēsop Virēre Eau de Parfum
This grassy, citirus scent from Aēsop is one of our favorite fragrance discoveries this year, and makes a excellent gift, given it’s versatility (and splashy sticker price).
DS & Durga Grey Blazer
In the year of our lord 2025, dressing the part just isn’t enough. Help him stand out from the crowd of Santal 33 and Pachouli with this heady scent from Brooklyn-based D.S. & Durga. As the name implies, Grey Blazer combines a host of sophisticated notes into one cruelty-free vegan cologne.
Stylish Stocking Stuffers
How Directors Dress by A24
Ever the best-dressed men on the planet get their ‘fitsperation from somewhere.
Drake’s + Him Embroidered Corduroy Baseball Cap
We see your Yankees fitted and raise you a cheeky, pup-embroidered corduroy cap from our friends over at Mr Porter.
Howlin A New Space Scarf
You can never go wrong with a nice winter accessory — this scarf from Scandi label Howlin balances playful and sophisticated perfectly.
Würkin Stiffs Magnetic Power Stays
You get the satisfaction of knowing your sensible gift didn’t cost you an arm and a leg. He gets to be confident that he’s going to look sharp as hell for the entirety of the work day.
Bombas Lodge Sock (4-Pack)
We don’t know who decided that socks were a lame gift, but clearly, they’ve never popped on a pair of hefty, ribbed Bobmas mid-calves before.
The Best Splurge Gifts
Unimatic U4 Classic Military Watch
Gifting the watch-lover in your life can be difficult, given that he almost certainly knows more about what to get than you do. This Unimatic is a safe bet — made in Italy and modeled after classic diving watches, it’s rugged enough to function as a daily driver and unique enough that he won’t be embarrassed to wear it.
Reigning Champ Cabin Fleece Logo Relaxed Robe
A fleecy robe is as classic as it gets. Reigning Champ has figured out how to do one exceptionally well.
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We've put in the work researching, reviewing and rounding up all the shirts, jackets, shoes and accessories you'll need this season, whether it's for yourself or for gifting purposes. Sign up here for weekly style inspo direct to your inbox.