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

This holiday 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.

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; something that showcases the craftsmanship of the company that made it. Case in point—a cashmere sweater by Loro Piana will never go out of style, or a pair of leather-and-cashmere gloves, for that matter.

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.

Dents Gloucester Cashmere-Lined Leather Gloves

This stylish pair of gloves is the epitome of luxury. Crafted from genuine deer leather dyed in a beautiful dark brown hue, each glove is lined with warm and soft cashmere. The gloves sport elasticized cuffs for a better and more comfortable fit in addition to the gold hardware accents and beautiful stitch details.

To buy: $180,

Kingsman + Johnstons of Elgin Fringed Logo-Embroidered Cashmere Scarf

A scarf is just as much a stylish accessory as it is a necessity in the wintertime. For over two centuries, Scottish company Johnstons of Elgin has been producing garments and accessories only from the finest fabrics sourced from around the world and this camel-hues scarf is no exception. It’s crafted from soft cashmere in the company’s plant in Scotland and features Kingman’s embroidered logo as well as fringed ends.

To buy: $240,

Salvatore Ferragamo Adjustable & Reversible Gancini Buckle Belt with Briarwood Detail

A leather belt is a wardrobe staple. This Salvatore Ferragamo one has a classic look so it can be styled with a variety of outfits and it is super practical because it’s reversible. So its owner has two color options to choose from—black and dark brown. It is of course made in Italy from calfskin leather and sports the company’s signature Gancino logo.

To buy: $395,

Loro Piana Cable-Knit Baby Cashmere Sweater

This holiday season, give the gift of the luxury and elegance that Loro Piana stands for. The company prides itself on using only the finest cashmere in the world and this beautiful sweater proves it. It has a classic cut and dons a beautiful pattern—the perfect piece to wear on a chilly night by the fireplace.

To buy: $1,795,

Derek Rose Men's Brindisi 40 Striped Silk Pajamas

The holidays are the perfect time of the year to put on pajamas and enjoy a movie or a book with a hot drink in hand. Any gentleman will love lounging in this luxurious silk PJ set that comes in a stylish striped pattern. The top has a classic three-pocket design and the pants have an adjustable two-button waist plus a side elastic for a comfy fit.

To buy: $885,

Celine Men's Square Acetate Sunglasses

A pair of cool shades is a must-have year-round. And there’s nothing cooler than Celine. We love this pair of acetate sunglasses in black because of the classic square shape of the frames that would look great on a variety of face shapes. The lenses guarantee 100 percent UVA protection.

To buy: $500,

Tom Ford Men's Velvet Evening Bow Tie

Help someone you love look dapper this holiday season thanks to this gorgeous velvet bow tie in navy. It is the perfect accessory to formal evening attire such as a sharp suit or a tuxedo. And since it comes pre-tied, it will always look impeccable.

To buy: $260,

Brunello Cucinelli Men's Pebbled Leather Duffel Bag

How gorgeous is this Brunello Cucinelli duffle?! Crafted from rich pebbled leather in a stylish brown hue, it has a zip-around top closure and a smooth leather trim. It fits a couple of days worth of belongings so it’s the perfect bag to pack for a quick weekend getaway. In addition to the roomy interior, it also sports two side zip pockets.

To buy: $4,295,

Saint Laurent Men’s Rabbit Felt Fedora Hat

There is something incredibly chic about a man wearing a felt fedora in the wintertime. It always makes us think of Humphrey Bogart’s character in the 1942 classic Casablanca. If you know someone who agrees with us then he will definitely appreciate this Saint Laurent hat made in Italy from warm rabbit felt. It features a pinched crown and a black grosgrain band.

To buy: $995,

Fendi Silk Logo Eye Mask

Getting a good night’s sleep is one of life’s luxuries these days. This Fendi silk mask will make the stylish frequent traveler in your life very happy as it will definitely help him catch some Zs while on the road. It’s made with goose feathers and has Fendi’s logo printed all over its front.

To buy: $350,

Tiffany & Co. Double Knot Cuff Links

This year, Tiffany & Co launched its first-ever men’s collection of luxury accessories which make the perfect holiday gift. These sophisticated cuff links in sterling silver sport the company’s signature knot design and are for those gentlemen who enjoy classic details (and the sight of a Tiffany blue gift box).

To buy: $500,

Sennheiser Momentum True Wireless Earbud Headphones

Most headphones are too bulky and look out-of-place on someone who favors a more traditional and toned-down approach to dressing. These in-ear headphones will help him enjoy his favorite tunes while not messing up with his look. Their compact and sleek design in black and silver fits securely into the ear while they deliver a powerful listening experience.

To buy: $250,

Ermenegildo Zegna Solid Two-Piece Solid Wool Suit

For over a century, Zegna has stood for quality and style so when it comes to elegant menswear and especially suits, nobody does it better than them. The jacket of this two-piece wool set sports two-buttons, notched lapels, and flat pockets for a classic look appropriate for a multitude of occasions.

To buy: $2,795,

Hermes H Attack Silk Pocket Square 45

Pulling off a pocket square is almost an art form (you can read more about it here) but just like with anything in fashion, it’s a matter of finding the right one for you. And when it comes to pocket squares, we really can’t think of a better brand than Hermès. The company is famous for its pocket squares made from luxury silk that sport Hermès’s vivid patterns.

To buy: $160,

Rimowa Cabin S Suitcase

Know someone who likes to travel light? Like really light? Then this Rimowa carry-on is perfect for him. It features the brand’s signature ribbed hardshell exterior but weights 30 percent less than its regular suitcases. It features TSA-approved locks, a telescopic handle, and Rimowa’s proprietary multi-wheel system that will help your loved one effortlessly (and stylishly) glide his way through any airport.

To buy: $490,

The Art of Shaving Mach 3 Engraved Nickel Plated Shaving Set

One reviewer called the stand of this sleek shaving set “elegant and classy —representative of how you should look after using the Art of Shaving” and we couldn’t agree more. Built to last, this nickel-plated shaving set will help your loved one look his best every day. Both the brush and the razor have engraved handles which makes not only for a good look but also helps for a secure grip.

To buy: $585,


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