The 50 Best Gifts for the Stylish Man in Your Life

Because what is better than free clothes?

November 25, 2020 11:41 am
The 50 Best Gifts for the Stylish Man in Your Life
Filson, Stussy, Saturdays

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

If you know someone invested in fashion and style, then you know they are suffering. Months upon months of wasted or completely missed fit opportunities. You might be inclined to think that as a result these discerning individuals don’t need or even desire new clothes, that it would be too painful, but in fact it’s the opposite. Now more than ever, the sartorially inclined among us are in desperate need of new fashions, as it’s the only thing that’s keeping them afloat — the possibility of once again being able to wear an outfit.

So this holiday season, do the right and generous thing and gift these hurting persons not with useless kitchen appliances or impersonal gift cards, but instead shower them with sweaters, bags, socks, shoes, scarves, coats — basically any and every type of garment and accessory. In turn, not only will you get the serotonin boost that comes with making someone happy, you’re potentially contributing to a future fit, the results of which could be groundbreaking.

Below are 50 gifts the clotheshorse in your life will more than approve of, from sweaters worn by Princess Diana to cashmere tie-dye beanies and even a water bottle.

Rowing Blazers

Warm & Wonderful x Rowing Blazers Sheep Sweater

While Rowing Blazers’ replica of Warm & Wonderful’s sheep jumper is only available for pre-order and won’t ship until some time in February or March, it’ll be well worth the wait, seeing as how it’s the exact same design Princess Diana famously sported in 1979. After all, she wasn’t just the “people’s princess” — she was (and is) the people’s style icon, too.

Noah NY

Noah Double-Pleat Corduroy Trouser

Corduroys are the unofficial-official pants of fall and winter, so to make sure the guy you’re shopping for is living cords season to the fullest, you’re going to want to get him this chocolate brown pair from Noah. Crafted from a heavyweight corduroy, this isn’t the kind of pair he’s going to wear for one season then toss ’em the next. No, these are bound to become the corduroy pants at the top of his rotation for seasons to come.

Todd Snyder

Paraboot Michael Bison Shoe

For those who have always admired Doc Martens but felt they lacked the proper punk attitude to convincingly pull them off, French brand Paraboot offers a similar silhouette, yet more refined and sophisticated. The durable rubber soles nicely offsets the luxuriousness of the rich brown leather, making for a shoe that’s neither too casual nor too formal.

Matches Fashion

Desmond & Dempsey Sansindo Tiger-Print Pajamas and Eye Mask

Any fashion-conscious man knows that looking good is a 24-hour job, conscious or not. Desmond & Dempsey’s pajama set (with matching eye mask!) will be the perfect gift for the guy determined to pull off a ‘fit even while asleep.


Adelante Shoe Co. Luca Penny Loafer

Every man should own a pair of classic brown penny loafers. Stylish, versatile, timeless. Adelante does them right — each pair is sewn by hand to order by skilled Guatemalan craftsmen (all of whom are paid over the Living Well Line) from full-grain leathers, lined with calfskin and Goodyear welted. Our favorite colorway is the mahogany (pictured), a deep brown that will look smashing with a pair of cuffed jeans and woolly socks this season. That being said, Adelantes are fully customizable, so live your life. Oh, and for a limited time every pair on the site is 20% off.


Goodlife Micro Terry Crew Sweatshirt + Micro Terry Scallop Shorts

When it comes to spending extended periods of time in your domicile — which, let’s be honest, is very much on our collective horizon — we cannot overstate the value of a matching crewie/short combo. It’s comfy and lounge-y, sure, but it still feels put together and considered. Goodlife’s set is crafted from cozy loop cotton terry with just the right amount of stretch, and it comes in a staggering ten different colorways — so unless you’re a true hue diva, you should be able to find something that suits you.


Everlane Selvedge Slim Fit Jean

One cannot truly consider themselves a connoisseur of denim unless they have experienced the wonder that is selvedge denim. Typically considered superior for its ability to mold to the wearer’s body over time, as well as its durability, the particular type of fabric tends to come at an exorbitant cost. Luckily Everlane is offering their own pair of selvedge jeans for less than a $100, without skimping on style or craftsmanship. Made from denim woven and dyed at the Candiani Mill in Ticino Park, Italy, the jeans feature just a hint of stretch to make the process of breaking them in a little more bearable.


Abercrombie & Fitch Pattern Shawl Cardigan

2020 has proven to be the year of the cardigan, but to tailor the trend to the holiday season, we’re opting for this shawl-collared option from Abercrombie & Fitch. Complete with moose and pine trees, it’s just festive enough, without veering even slightly into ugly Christmas sweater territory.


Levi’s Made & Crafted Quilted Zip Jacket

When it comes to the trucker jacket silhouette, Levi’s is the gold standard — they’ve been doing them since 1962 after all. This season, the company’s premium Made and Crafted arm dropped this handsome number in a deep caramel diagonally-cut corduroy, with a quilted interior and sherpa collar/cuffs for warmth and minus the exterior chest pockets for a more streamlined vibe. We’re not going to tell you that you need to cop the matching pants, but we’re also not not going to tell you that.


Entireworld Six Solid Socks

A colorful pair of socks for nearly everyday of the week.


Supreme by Supreme

If you tried your luck at snagging something from a Supreme drop but we’re beat out by hypebeasts, get him the next best thing — a book detailing the streetwear brand’s 25-year history, replete with photos from Larry Clark and David Sims, as well as plenty of envy-worthy imagery of some of the brand’s most iconic and sought-after pieces.


Burberry Classic Check Cashmere Scarf

As far as gifts go, a scarf is fairly middle-of-the-road. Not bad, certainly, but not really one to write home about, either. Unless, of course, that scarf sits at the center of a Venn diagram that has “cashmere” on one side and “world’s most iconic plaid” on the other. Throw in a free custom monogram and all of a sudden said scarf is a holiday all-timer.

Ralph Lauren

Ralph Lauren Custom Packable Jacket

We clued you into this one back when it dropped a few weeks ago, but it bears repeating: for the first time ever, Ralph Lauren now allows you to custom design your own puffer (hooded, mock neck or vest) via a nifty online tool that features literally thousands of options for customization. Each piece is built to order from recycled materials, which means less waste and a healthier planet. Plus a monogrammed stuff sack and interior label where you can drop a holiday message to your recipient.


J.Crew Unisex 1988 Cotton Rollneck™ Sweater

After endless begging on the part of faithful customers, J.Crew has finally delved into the archives to bring back their iconic rollneck sweater, and it remains as classic as ever. Available in three colors, we’re partial to the off-white, particularly for it’s ability to lend the wearer leading man in a 90’s rom-com vibes.

Richer Poorer

Richer Poorer Terry Trouser

This year has continuously been dubbed one of sweatpants, but not everyone has been made a convert of the leisure-wear lifestyle. So for the guy who still has yet to relinquish his jeans, even while in the comfort of his own home, help him make the transition to more comfortable apparel with these terry trousers from Richer Poorer. Far from the ubiquitous gray sweatpants, these French terry sweats feature pintucking and faux J-stitch tailoring details, as well as a cuffed hem, for an elevated take on the casual basic.



We talk about this line of swaggy, hand-sewn Turkish slippers a lot, and to be honest we’re going to keep doing so until there is a pair on the feet of every InsideHook reader. Sabahs — and their backless cousin, Babas — are not only crazy comfortable (they mold to your feet over time in the most satisfying way), durable (our EIC has been wearing the same pair since 2015) and versatile (we’ve seen them paired equally well with a tanktop/swimsuit and a tuxedo), but owing to their unique silhouette and array of standout colorways, they’re also virtually guaranteed to garner comments/compliments every time you wear them. 

Alex Mill

Alex Mill Cashmere Beanie in Tie Dye

Beanies are a dime a dozen this time of year, but a cashmere tie-dye beanie? Well, those are a bit harder to come by, but if your interest is piqued, look no further than Alex Mill, who’s currently offering a 100% cashmere beanie in a trippy, multi-color tie-dye. Consider it the perfect melding of high-brow (luxurious cashmere) with something a little more low-brow (i.e. the DIY craftiness of tie-dye).


Gramicci Boa Fleece Jacket

Fall and winter are seasons populated by fleeces, and while recent years have seen a predominance of conspicuous patterns and colors, sometimes it’s nice to return to the basics. What Gramicci’s Boa Fleece might lack in color, it certainly more than makes up for in design, evident in the mandarin collar, curved hem and nylon elbow patches.


Smythson Mara Card Holder

Chances are the guy you’re shopping for could do with some consolidating when it comes to his wallet, so drop a hint with this leather croc-embossed card holder from Smythson. The wallet features five card pockets so he’ll be forced to carry only the absolute necessities, thus saving himself from the dreaded wallet bulge.

Saturdays NYC

Saturdays NYC Marco Plaid Flannel Green Shirt

Sure, he probably has a few flannels among his wardrobe, but we’re willing to bet all of them lack a camp collar. Typically a silhouette seen only in spring and summer, Saturdays NYC has blessed us with the ability to carry the style into the colder months by adding it to their brushed cotton flannel. The collar immediately lends the shirt an entirely different look, like that of a refined lumberjack.


Wolverine 1000 Mile Faribault Boot

Wolverine has been hand-crafting quality leather boots in Rockford, MI, since 1883. Up in Minnesota, Faribault has been turning out top-shelf woolen goods since 1865. That’s a combined 292 years of fine American craftsmanship, culminating in one helluva collab. Horween Chromexcel leather construction offset with Faribault wool panels in either green or grey, the former inspire by the blankets the company used to make for the US Army, the latter the Navy. Add a Vibram lug outsole and you’ll be high-stepping right through winter.

Aimé Leon Dore

Aimé Leon Dore Suede Cap

Okay, this hat isn’t suited for rainy days, lest you ruin the beautiful suede, but that shouldn’t dissuade you from buying it. Just think how even the simplest of outfits will be transformed with the addition of this one accessory.

Urban Outfitters

The North Face Eco Nuptse Recycled Puffer Jacket

Whatever your feelings regarding puffer jackets, we can all agree that The North Face has long since made the best and continues to do so. The Nuptse Jacket gleans inspiration from the brand’s 1996 version of the same, and it features a boxy silhouette and 100% recycled materials that are bound to keep you warm. You’ll look like a toasted marshmallow, in the best way possible.


Topman Ecru Straight Jeans

For the man brave enough to throw all caution to the wind and wear white jeans (well, ecru) not only well past Labor Day, but in winter at that.


Persol PO3245S

We’re all familiar with Persol and their famed 649s and 714s, but not all of us are Steve McQueen. Luckily the brand offers a vast selection of simpler silhouettes that are easier to pull off, like their new PO3245S style. The simple shades feature a square shape that’s slightly rounded, with thick temples. They’re the kind of sunglasses that’ll make you look sleek and mysterious and maybe even like a movie star.

Wolf & Shepherd

Wolf & Shepherd Monaco Loafer

You ain’t gotta be the King to rock a pair of blue suede shoes. All you really need is a devil-may-care attitude and a pair of these bad boys from Wolf & Shepherd, which are unlined and thus the most pliable, butter soft loafers you will ever lay your hands on or your feet in. Wolf & Shepherd’s founder previously designed shoes at Adidas and New Balance, which means he’s also bringing tech details like an extra-cushy internal footbed and waterproof suede to the table. 


Bonobos Wool Car Coat

A handsome and elegant man deserves an equally handsome and elegant coat, like this one from Bonobos. Staying true to the classic car coat silhouette, the piece is lent a slightly vintage aesthetic thanks to the tan houndstooth, without managing to feel dated in the slightest. It’s a coat that calls to the past while transcending time.

Coming Soon

Coming Soon Nalgene Water Bottle

In case you haven’t heard, the hottest accessory is a reusable water bottle, specifically one that hints at some niche interest or references an ultra-cool emerging brand. Take these Nalgene bottles from Coming Soon for example, available in two fun colorblocked iterations bearing the name of the funky Lower East Side furniture store at which they’re sold.


Filson Wool Fisherman’s Sweater

Now that the fisherman sweater has long been established as a classic, it’s time to have a little fun with it. You could opt for the standard off-white sweater, or you could go in the completely opposite direction and choose this vibrant one from Filson in a hunting-approved orange.


Gucci Ophidia Web Keychain

A keychain so nice (and expensive) that he’ll do everything in his power not to lose his keys — or else.

End Clothing

Barbour SL Bedale Jacket – White Label

Go ahead and not only make his holiday but his whole year with Barbour’s Bedale Jacket. This particular style is from the brand’s White Label, which takes traditional Barbour silhouettes and slims them down. But don’t worry, all the classic Barbour detailing remains, from the waxed cotton to the corduroy collar.


Stüssy S Chain LS Knit Polo

All those times re-watching The Sopranos are bound to take their toll, so when he starts expressing a desire to dress just like Tony, gift him with this chic yet gangster-appropriate knit from Stüssy, rather than a velour tracksuit.

Freemans Sporting Club

Evolg Tori Knit Gloves

Gloves tend to be a nuisance, as one is constantly taking them off and putting them on in order to do anything that involves the use of their hands, but the Tokyo based brand Evolg (that’s glove backwards) has managed to solve our problems. Their multi-colored knit gloves are crafted with a conductive yarn at the fingertips to allow you to still use your phone without sacrificing your hands to the bitter cold.


Standard Issue Leather Gym Duffel

It’s only fitting (and deserved) that his travel companion be as stylish as he is.


Clarks Original Desert Boot

The same Clarks Desert Boots you know and love, now rendered on a deep violet that borders on navy, and will definitely leave others doing a double-take.


KULE Patch Rugby

Who knows how many rugbys had to be sacrificed for the sake of this one shirt? But if you’re of an indecisive mind, at least you’ll have a lot less trouble deciding what to wear in the morning, seeing how this shirt is comprised of at least six others. Consider it shirt-ception.

East Dane

WANT Les Essentiels Kenyatta Dopp Kit

A dopp kit equipped to make even the most mundane of morning routines all the more exciting and luxurious. And if you don’t have a routine, you’ll be inspired to develop one just so you have an excuse to use this bad boy.

Freemans Sporting Club

Borderstate Star Geometric Pattern Belt

While it’s safe to assume most men have a black belt in their possession, we doubt there cut from American saddle leather then vegetable dyed by hand in Kentucky, or that they feature intricate geometric designs that are hand-tooled and stamped. But, if such a belt appeals to you, you know what to do.


Flint and Tinder 10-Year Crew

Yes, you could have the honor of introducing someone to the wonder that is Flint and Tinder’s 10-Year Crew. For the uninitiated, the sweatshirt is constructed from a hefty 23 oz that’s then expertly cut, sewn and washed to achieve a piece of clothing that will only grow softer with each wear for a decade to come.


Adidas x Wales Bonner SL72

Rising menswear fashion designer Grace Wales Bonner brings her delicate and vintage-inspired touch to a range of Adidas classics for her latest partnership with the brand. Bonner leans into the SL72’s seventies roots, rendering it in dark hues of burgundy and forest green, starkly contrasted against the pale yellow three stripes and subtle mint green accent along the sole.


Uniqlo Balmacaan Coat

When it comes to the canon of fall and winter outerwear, there’s one style that tends to get shut out from the conversation: the Balmacaan coat. The often forgotten coat is marked by its loose fitting silhouette with a fly front and raglan sleeves. It’s the kind of coat that looks like true, traditional menswear, and deserves to be worn and seen.


Miansai Geo Signet Diamond, Gold

There’s nothing hotter than a guy confidently wearing some decorative pieces of jewelry, especially if it’s a signet ring. Rather than go the traditional route, opt for an updated take on the classic piece of jewelry, like Miansai’s rectangular signet that features just the tiniest bit of bling.

R.M. Williams

R.M. Williams The Yard Boot 365

Fellow Australian designer Marc Newsom teamed up with R.M. Williams to create The Yard Boot 365, a Chelsea boot inspired by the footwear brand’s Gardener Boot first introduced in the 1950s. While most of the silhouette remains true to the brand’s other Chelsea styles, the most noticeable difference is the sole, this one made of rubber to lend the boot a more hard-working feel that pays homage to the style by which it was inspired.

Mr Porter

Patagonia Market Logo-Print Organic Cotton-Canvas Tote Bag

Channel both granola and normcore with Patagonia’s (organic, of course) cotton-canvas tote. It’s the perfect way to show you care but, like, in an aesthetically pleasing and completely on-trend kind of way.


Tombolo “Disco Fungi” Cabana

It’s time to start thinking of terry cloth as a fabric not just for warmer weather, and it’s time to start with Tombolo’s ‘Disco Fungi’ shirt. The 70s-esque shirt is still appropriate for wear in the fall and winter, due to its terracotta and blue pattern, as well as the embroidered dancing mushrooms. Groovy.

Todd Snyder

Todd Snyder Stretch Moleskin Madison Suit Trouser

You might think the need for trousers, aka real pants, at this point in time is nonexistent, but you never know when you’re going to feel like getting a little dolled up for the grocery store. Todd Snyder’s Madison Suit Trousers are cut from a soft, imported moleskin that has just a hint of stretch, making the experience of wearing them insanely comfortable. Throw them on with a sweater and sneakers for the perfect casual but not too casual look.

Mr. Porter

Cleverly Laundry Striped Cotton-Terry Robe

Even style icons need a little R&R, and what better way to enjoy it than with Cleverly Laundry’s pea-green striped robe? Slip into the ultra-plush terry and you’ll feel like you’re resting on a cloud.


Ugg Tasman Slipper

To be paired with the aforementioned robe, obviously. These aren’t your normal house shoes — just peep that decorative stitching around the ankle.


Coach Reversible Shearling Coat

If you wanna win the holidays, you gotta go big or go home.

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