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

Tom Werner/Getty Images

This holiday season, give the gift of impeccable looks.

Each product we feature has been independently selected and reviewed by our editorial team. If you make a purchase using the links included, we may earn commission.

In a world where athleisure has reigned supreme, there are some men who still 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, even while socially distancing. They make us believe that the art of dressing up is not yet lost.

Related: What Our Editors Are Shopping for This Holiday Season

So, if you have such men on your holiday shopping list, we are here to help. 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 an of-the-moment design 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 become a classic staple in his closet.

Keep reading for a lot more ideas for stylish gifts for the most dapper-looking guy in your life.

FPM Milano Leather-Trimmed Aluminium Vanity Case

Courtesy Mr. Porter

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, mrporter.com

Valstar Valstarino Suede Bomber Jacket

Courtesy Mr. Porter

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, mrporter.com

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

Courtesy Mr. Porter

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: $1,400, mrporter.com

Persol Tortoise/Brown Polarized Sunglasses

Courtesy Sunglasshut

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: $310, sunglasshut.com

Parajumpers Masterpiece Kobuk Vest

Courtesy Parajumpers

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, parajumpers.it

Gucci BB Felt Fedora

Courtesy Saks Fifth Avenue

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, saksfiftahvenue.com

Montblanc Meisterstruck Solitaire Geometric Dimension Rollerball Pen

Courtesy Saks Fifth Avenue

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, saksfifthavenue.com

Saint Laurent Flap Two-Way Bag

Courtesy FarFetch

This elegant leather tote turns into a messenger thanks to its flap design and a removable strap. It will help the stylish man in your life carry his belongings however he feels most comfortable doing so.

To buy: $1,490, farfetch.com

Ermenegildo Zegna Tiziano Sneakers

Courtesy FarFetch

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, farfetch.com

Bally Tonni Reversible Belt

Courtesy Neiman Marcus

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, neimanmarcus.com

Shinola Third Man Record Edition TT Gift Set

Courtesy Neiman Marcus

This is an exquisite gift set for the melomaniac in your life with a taste for the fine things in life.

Shinola teamed up with VPI industries on a sleek turntable crafted from aluminum and solid oak. It has a removable magnetic grille and comes with a bookshelf speaker system that connects to the turntable in a number of ways, including Bluetooth. 

The gift set also features eight vinyl records that include classics from Diana Ross and The Supremes as well as some modern tunes by the White Stripes and The Raconteurs.

To buy: $3,995, neimanmarcus.com

Astis Kibo Ski Gloves

Courtesy Astis

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, astis.com

Hublot 40th Anniversary Yellow Gold

Courtesy Hublot

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, hublot.com

Louis Vuitton Monogram Chain Stole

Courtesy Louis Vuitton

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, louisvuitton.com

Dior Bow Tie with Bee Jewel

Courtesy Dior

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, dior.com

Gillette Gillettelabs Heated Razor Starter Kit

Courtesy Amazon

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, amazon.com

Kiton Men's Washed Cashmere-Cotton Sweater

Courtesy Bergdorf Goodman

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, bergdorfgoodman.com

Tom Ford Black Orchid Parfum

Courtesy Bergdorf Goodman

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, bergdorfgoodman.com

Tumi International Carry-On

Courtesy Tumi

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, tumi.com