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What to Get the Most Stylish Gentlemen in Your Life for the Holidays

This season, give the gift of impeccable looks.


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In a world where fast fashion and athleisure reign supreme, there are still men who have an appreciation for the finer things in life. And they are our favorite people to shop for during the holidays. No, not because it’s so easy to meet their high standards but because their joie de vivre is admirable and contagious. They are always dressed to the nines regardless of what time of the day or week you meet them, and that deserves great respect. They make us believe that the art of dressing up is not lost yet.

So if you have such men on your holiday shopping list, we are here to help guide you through the countless gift options that the market of luxury goods offers. While choice can be a good thing, we know very well that more often than not, it’s also incredibly difficult to pick just one item in a sea of wonderful alternatives.

Related: What Our Editors Are Shopping for This Holiday Season

We are firm believers that less is more when you are shopping for a stylish friend or family member. Focusing on quality and a classic look rather than trendy design that may become obsolete in a couple of seasons is the way to go. For example, if you have decided to gift something on the standard side such as a sweater or a scarf, go for one that is made from the finest fabrics and that will last him a long time.

And these are just two options that will make any gentlemen happy. Keep reading for a lot more ideas for stylish gifts for the most dapper-looking guy in your life.

Fear of God Exclusively for Ermenegildo Zegna Leather Trousers

What happens when one of the most exciting brands in men’s fashion, Fear of God—lauded for luxury goods dripping in cool cred—teams up with storied house Ermenegildo Zegna? A sophisticated collection of sleek, tailored staples that’s on every fashion-lover’s wish list. Act fast, this buttery leather trouser, featuring a slim fit and Fear of God’s signature elongated belt, won't last long.

To buy: $2,890,

Ooni Koda 16 Gas Powered Pizza Oven

Did someone say pizza party? Outdoor entertaining is the safer way to spend time with friends and family these days. This sleek compact tool is a fun alternative to grilling outdoors and reaches a scorching 932 degrees F in 60 seconds for delicious Neapolitan-style pies. But that’s not all: fish, seared steaks, and even fresh bread can be prepared in the Ooni. Just brace yourself to use his new favorite outdoor oven all of the time.

To buy: $499,

Dries Van Noten Rabble Long Wool-Blend Coat

Now more so than even outerwear is key. Afterall, stepping out to run errands, go for a walk, or dine outdoors is when we’re in contact with the outside world. He’ll make a statement in Dries Van Noten’s elegant and classic wool topcoat. The boxy silhouette works just as well with jeans and sneakers as it does over a suit. And the plush lining adds a layer of coziness.

To buy: $1,585,

Ermenegildo Zegna Henley Pajama Set

Good men’s pajamas are hard to come by. There aren’t too many options that are well-made, and well, feel modern. Pamper him with Ermenegildo Zegna’s comfy modal-blend set. It’s breathable, soft, and features contemporary elements like a crew neckline, henley placket, and elasticized waistband.

To buy: $400,

Rimowa Original Cabin Special Edition Camouflage

Whether he’s hitting the slopes for the weekend or heading on a business trip, Rimowa’s special edition luggage in chic silver and green camouflage will add some flair to his travels. Crafted in high-end aluminum, this iconic design is lightweight and made to fit in most airplane overhead compartments. We doubt there’ll be multiple versions on any flight, but just in case the bag includes a complimentary leather luggage tag and sticker set.

To buy: $1,470,

Saint Laurent Men’s Logo Script Hoodie

Resist the urge to steal this gift for yourself. Saint Laurent’s hoodie, featuring vintage script, is the kind of effortless cool staple the brand has come to be known for. Expect to see him in this a lot.

To buy: $850,

Louis Vuitton Men’s Multiple Wallet Niloticus in Vert Foret

Consider it an heirloom piece. Louis Vuitton’s sexy Multiple wallet, crafted from crocodile leather features numerous slots for cards and receipts to keep him organized. Oh and heads up, this striking green shade will constantly draw admiration from passerbys.

To buy: $4,250,

Leica TL2 System Digital Camera

Sure iPhones are great but budding photographers want a real camera. This easy-to-use model boasts fast sequential shooting and can record HD and 4K videos. But the true beauty of the German made design is its ability to capture sharp, focused images in any light. Bonus features include a touchscreen display and WiFi connectivity, making transfering images to social media a snap.

To buy: $1,950,

Officine Generale Wool Flannel Elastic-Waist Pants

Perfect for winter. And to ease back into wearing real clothes after months of strictly lounge wear, these handsome wool trousers boast an elastic waist. He’ll be comfortable and stylish for Zoom calls even after loading up on Holiday fare.

To buy: $390,

David Yurman Men's 18k Gold Box Chain Necklace, 22"L

Call it the Connell effect. Our (probably unhealthy) obsession with the central character on Normal People, and his jewelry, have boosted interest in men’s chains. (By the way, at present time Connell’s Chain has its own IG account with 180K followers.) It’s only fitting then the stylish guy in your life needs one, too. We especially love David Yurman’s understated classic gold box chain.

To buy: $2,825,

Tom Ford Leather AirPods Case with Lanyard

He literally needs (and loses) his AirPods every second. Make sure they stay by his side with Tom Ford’s chic and useful case. Made in Italy from full-grain leather, it also doubles as a cool necklace.

To buy: $550,

Diemme Roccia Vet Debossed Leather Hiking Boots

Hiking is basically a regular weekend passtime these days so invest in a quality and cool pair of boots. Diemme, handcrafted in Italy, is inspired by hikers and skiers but adapted for urban life with lighter soles. Other well-thought touches include suede trimming, padded linings, and ankle support. But really we love the brand’s colorful laces.

To buy: $450,

Aimé Leon Dore Down Puffer Jacket

When it comes to puffers, black is boring. Help him stand out from the crowd in buzzy New York label, Aimé Leon Dore’s ochre version. This ultimate utilitarian essential features a two-way zip closure, a chest pocket in addition to hand pockets, and elasticated cuff. The style also comes in a zippy green and sleek black.

To buy: $450,

Stubbs and Wootton Zachary Weiss Collection Liquid Lunch Slippers

Miss fancy hotel stays? Man about town Zachary Weiss sure does. Specifically late nights at the St. Regis Hotels. His collaboration for bespoke slipper brand Stubbs and Wootton cheekily pays homage to those carefree days of ordering club sandwiches and sipping champagne for lunch. Remind the guy in your life of the fun that’s waiting post-Covid and keep him cozy in these green velvet slippers. Cocktails not included.

To Buy: $550,

Vilebrequin Swim Trunks in Les Geckos

Capturing the spirit of St. Tropez in the 1970s, Vilebrequin knows what you need from vacation wear—especially while playing on the beach or lounging by the pool. It’s comfort (their swim shorts feature elastic waistbands and drawstrings), practicality (a Velcro fastened back pocket keeps belongings from disappearing), and fun (just look at this colorful, island inspired lizard print!).

To buy: $260,

Creed Aventus 10th Anniversary Limited Edition

It’s the 10th anniversary of Creed’s cult-classic fragrance. To celebrate, the heritage fragrance house introduced a limited-edition bottle in sexy matte black and silver accents. The signature scent, with notes ranging from fruity (bergamot, apple, pineapple) to rich (patchouli and musk among others) will thankfully stay the same.

To buy: $435 for 3.4 oz,

John Elliott Escobar Sweatpants

Face it, loungewear reigns supreme. This doesn’t mean wearing any ol’ frumpy sweats. John Elliott’s slim fashion forward sweatpants, taper from the knee to cuff, add some much needed edge to everyone’s favorite casual look.

To buy: $248,

FPM Milano Leather-Trimmed Aluminium Vanity Case

Mr. Porter just launched an exclusive collection of items by a number of luxury Italian brands that represent the best of the country’s craftsmanship. FPM Milano’s luggage pieces are crafted only with the best materials and ooze a modern aesthetic. This vanity case was made with durability and style in mind. It can be used to store watches, jewelry, or tech gadgets since it has a fully lined interior with a divider and zipped pockets.

To buy: $995,

Valstar Valstarino Suede Bomber Jacket

Valstar made a name for itself by putting a modern spin on the classic military bomber jacket and, thus, transforming it into a closet staple for men around the world. This gorgeous Valstarino is cut in a classic silhouette and is crafted from supple suede. The jacket features two exterior pockets and another interior one, perfect to carry for smaller items.

To buy: $1,200,

Missoni Shawl-Collar Crochet-Knit Wool and Cotton-Blend Cardigan

Tired of gifting sweaters? Then opt for this vibrant Missoni cardigan crafted from a blend of wool and cotton. It sports an elegant shawl collar and can be styled with a t-shirt or a casual shirt underneath.

To buy: $1,130,

Persol Tortoise/Brown Polarized Sunglasses

Every stylish man has to have a pair of Persol sunglasses. Designed and crafted in Italy, they’re classy, exclusive, and unique. Case in point? This pair designed with a tortoise frame and brown lenses has an Aviator-inspired shape and is available in five colorways.

To buy: $217,

Parajumpers Masterpiece Kobuk Vest

Italian luxury sportswear brand Parajumpers always designs its pieces with functionality and modern style in mind. This vest will keep a lucky someone warm and looking elegant all winter long (we think it’s an après-ski essential). It is crafted from waterproof nylon that has been laminated on the inside. It features two double-entry pockets on the outside and two mesh pockets inside. The high collar lined with faux shearling and the leather accents at the pockets add a casually elegant vibe to it.

To buy: $495,

Gucci BB Felt Fedora

This felt fedora from Gucci oozes so much class! It is the perfect gift for the well-suited gentleman who is not afraid to take it one step further with a statement accessory.

To buy: $615,

Montblanc Meisterstruck Solitaire Geometric Dimension Rollerball Pen

We all use pens on a daily basis so gifting someone a high-end writing instrument will turn a basic and mundane activity like signing receipts or documents into a luxury experience. And there’s no better way to do it than a Montblanc pen like this one. It is made in Germany from gold-toned resin and features a three-dimensional geometric pattern.

To buy: $1,285,

Ermenegildo Zegna Tiziano Sneakers

Sneakers are a wardrobe staple these days so they make for a great gift. For the man who’s not into their classic sporty aesthetic, though, this pair of elegant low top Ermenegildo Zegna kicks will do the trick. Crafted in Italy from premium calf leather in grey they sport bold orange accents and white rubber soles. Other eye-catching details include contrast stitching at the heels and branded leather panels on the soles.

To buy: $956,

Bally Tonni Reversible Belt

A good quality belt will last him for years to come, and this one by Bally is a styling powerhouse. The reversible design—a sporty striped web reverses to elegant solid black leather—makes it perfect for casual brunches as well as business dinners.

To buy: $275,

Astis Kibo Ski Gloves

Ski gloves are usually not the most exciting accessories when it comes to style but that’s not the case with this pair of Astis ones. They sport an intricate beadwork band across the hands that make for an eye-catching feature. The gloves are handcrafted in the U.S. from soft suede leather that has been injected with silicone for extra waterproofing. The gloves are also lined with an insulation layer for added warmth.

To buy: $165,

Hublot 40th Anniversary Yellow Gold

This year, Hublot marks the 40th anniversary of its groundbreaking design that combined gold and rubber—an unthinkable combination of materials at the time, especially, for a fine Swiss watchmaker. To celebrate the occasion, the company released an updated version of its 1980s Classic Original and it’s incredibly sleek. The timepiece has a 45mm 18-karat yellow gold case and a matching bezel with six H-shaped titanium screws. The black lacquered dial and the black rubber strap are a match made in Haute horology heaven.

To buy: $25,200,

Louis Vuitton Monogram Chain Stole

The luxurious blend of cashmere and silk makes this extra-large Louis Vuitton stole a cold-weather essential. The company’s iconic monogram is complemented by prints of loosely intertwined chains in different shades for a modern look.

To buy: $955,

Dior Bow Tie with Bee Jewel

A black bow tie is the epitome of class and elegance. This silk one by Dior takes things a step further. A crystal bee, inspired by Christian Dior’s passion for nature, adorns the bow tie adding whimsy and playfulness to it.

To buy: $300,

Gillette Gillettelabs Heated Razor Starter Kit

Gilette’s heated razor provides barbershop-worthy results without having to actually leave your bathroom. The soothing warmth of the razor feels like having a hot towel against the skin and completely transforms a mundane grooming activity into a spa-like experience.

To buy: $200,

Kiton Men's Washed Cashmere-Cotton Sweater

If you’d like to stick to the basics and gift a sweater to a stylish someone, then make it this luxury sweater by Kiton. Crafted in silky-soft cashmere and cotton blend in a beautiful baby blue shade, it cuts a timeless crew neck silhouette.

To buy: $1,995,

Tom Ford Black Orchid Parfum

Tom Ford’s signature Black Orchid fragrance has been given a 2020 update and it’s even more powerful than the original. With notes of black truffle, ylang-ylang, black plum, black orchid, patchouli, and rum absolute, it redefines what a masculine floral scent should smell like.

To buy: $195,

Tumi International Carry-On

With its new 19 Degree collection, Tumi wants to prove that travel is not just a utilitarian experience. Blending architectural lines with new materials, the collection is just as eye-catching as it is functional. This carry-on dons the signature 19-degree patterned design and has two TSA-approved combination locks for added security. Protective bumpers ensure that both the suitcase and its contents will be delivered damage-free.

To buy: $1,095,


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