Best Holiday Luxury Gift Guide Ideas for Most Stylish Man 2020

Still searching for the perfect gift for the most stylish guy you know? Scroll through for the luxe presents he'll love.

Julia Cherruault for Observer

Loro Piana Cable Knit Beanie
The most dapper man knows you can't beat Loro Piana, and he'll adore this deliciously soft cashmere beanie. $475, Mr. Porter.

Courtesy Mr. Porter

Desmond and Dempsey Corduroy Palm Tree Slippers
These cozy palm tree-embroidered slippers are like a tropical vacation for his feet. $91, Desmond and Dempsey.
Courtesy Desmond and Dempsey

Parachute Men's Waffle Lounge Set
Guys like matching lounge sets, too, like this ultra-comfy waffle cotton jogger ensemble. $149, Parachute.
Courtesy Parachute

Advertisement

Byredo Tobacco Mandarin Perfume
Byredo's latest edition to its Night Veils collection is unbelievably good. The fragrance is just the right amount of citrusy and spicy. $330, Byredo.
Courtesy Byredo

Orlebar Brown Bulldog Sicilian Summer Mid-Length Swim Shorts
A trip to Italy might be out of the question, but he'll love these cheerful swimming trunks, with a print of the Belmond Villa Sant'Andrea in Sicily, as a nice holiday alternative. $345, Orlebar Brown.
Courtesy Orlebar Brown

Courant Catch:3 Accessory Tray
Upgrade his WFH set-up with this leather accessory, which charges all his devices and helps organize all his extra knick knacks. $175, Courant.
Courtesy Courant

Advertisement

Man Crates Whiskey Appreciation Crate
Your favorite whiskey connoisseur will love this customizable gift set, complete with a decanter, glasses, ice molds, coasters, a journal and even salted treats. $159, Man Crates.
Courtesy Man Creates

Bespoke Post Gift Cards [SPONSORED]Bespoke Post is a monthly membership club delivering high-quality and seriously unique goods — from home and bar to outdoor gear, style picks, and more. Give the gift of a gift card worth the value of 1, 3, 6 or 12 boxes. $55 and up, Bespoke Post.
Courtesy Bespoke Post

Bruush Electric Toothbrush
You might not think of oral care as the most exciting of gifts, but we promise he'll love this sleek electric toothbrush, complete with six cleaning modes and a timer that tells you when to start brushing a different tooth area. $95, Bruush.
Courtesy Bruush

Advertisement

Gucci Brixton Horsebit Collapsible-Heel Leather Loafers
You can't go wrong with a pair of these classic leather loafers. $730, Mr. Porter.
Courtesy Mr. Porter

Skyline Chess London Marble and Acrylic Chess Set
Even if he's not exactly a chessmaster, he'll still enjoy this marble and acrylic set. $295, Mr. Porter.
Courtesy Mr. Porter

Banana Republic Cable Knit Scarf
A stylish and simple cable knit scarf he'll wear all the time. $80, Banana Republic.
Courtesy Banana Republic

Advertisement

Truff White Truffle Hot Sauce
Before you write off truffle-infused foods, we highly recommend testing out this hot sauce. $34.99, Truff.
Courtesy Truff

La Maison du Chocolat Holiday Cracker Advent Calendar
This indulgent 24-treat gift is perfect for the chocoholic. $70, La Maison du Chocolat.
Courtesy La Maison du Chocolat

Eberjey William PJ Set
The debonair man knows that super-soft matching PJ sets are the only acceptable sleepwear. $158, Eberjey.
Courtesy Eberjey

Advertisement

Edward Field Passport Holder
A leather passport case to prep for his next adventure. $97, Edward Field.
Courtesy Edward Field

Bluejay Premiere Edition Bike
This eco-friendly (and very chic) e-bike comes with a fancy motor, very long-lasting battery and is Gwyneth Paltrow-approved. Even if he's not Goop's biggest fan, he'll still love his new e-bike. $2,995, Bluejay Bikes.
Courtesy Bluejay Bikes

The Art of Shaving Heated Razor With Sandalwood Shaving Bundle
Treat him to an indulgent shaving kit. This set includes a heated razor, pre-shave oil, shaving cream and balm, in a lovely sandalwood scent. $300, The Art of Shaving.
Courtesy The Art of Shaving

Advertisement

Vuori Seaside Hoodie
An extra-comfy hoodie that's just as useful for a workout as it is for lounging around the house. $118, Vuori.
Courtesy Vuori

Theory Quilted Gloves
The most fashionable guy you know will love these quilted leather gloves. $195, Theory.
Coutesy Theory

Away Aluminum Carry-On Suitcase
Upgrade his luggage situation with this special aluminum-edition carry-on from Away. $475, Away.
Courtesy Away

Advertisement

Clase Azul Anejo Tequila
The tequila lover will adore this incredibly luxe gift, complete with a patterned bottle that depicts the evolution of agave. $500, Drizly.
Courtesy Clase Azul

Madewell Quilted Shirt Jacket
Gift him the perfect in-between-season jacket, for those days when he needs something to throw on over a sweater. $148, Madewell.
Courtesy Madewell

Bleusalt The Casa Pant
This comfy pant was designed for Cindy Crawford's husband, Casamigos co-founder Rande Gerber, so you already know it's supermodel-approved. $185, Bleusalt.
Courtesy Bleusalt

Advertisement

Maison Francis Kurkdjian Fragrance Wardrobe 8-Piece Discovery Collection For Him
Can't decide what scent he'll love? You can't go wrong with this eight-piece set, so he can try out a few different fragrances. $275, Saks Fifth Avenue.
Courtesy Maison Francis Kurkdjian

Theragun Elite Percussive Therapy Device
Elevate his workout routine with this Theragun, which helps to ease tension and soreness after just a few short minutes of use each day. $399, Nordstrom.
Courtesy Nordstrom

PopSockets PopWallet+ in Vegan Black Leather
The guy who hates carrying around a big wallet will definitely appreciate this tech gadget. $30, PopSockets.
Courtesy PopSockets

Advertisement

Carmina Norwegian Boots in Brown Suede
These beautiful suede boots, made by a fourth-generation family of Mallorca-based shoemakers, are sure to be a hit with the most stylish guy. They're classic but still on-trend, and so well-made. $555, Carmina Shoemaker.
Courtesy Carmina

Blenders Smooth Arrival Aura Snow Goggles
He'll be the most fashionable skier on the slopes with these new goggles, complete with anti-fog technology. $95, Blenders.
Courtesy Blenders

Nordstrom Four-Pack Masks
Masks might be the most crucial accessory at the moment (seriously, wear a mask!), so he'll definitely appreciate this addition to his collection, with four comfortable new styles. $20, Nordstrom.
Courtesy Nordstrom

Advertisement

Lord Jones CBD All-Natural Sugarplum Holiday Gumdrops
A very seasonal treat that combines the best of a classic candy gummy with CBD. $50, Lord Jones.
Courtesy Lord Jones

Five Two by Food52 Essential Cookware 11-Piece Set
He'll feel like a true chef with this shiny new 11-piece cooking set, complete with skillets, pots and pans, all fit for a culinary star. $429, Nordstrom.
Courtesy Nordstrom

Debut Carbon EVO Turntable
A glossy black turntable for your favorite music enthusiast. $499, Pro-Ject Audio.
Courtesy Pro-Ject Audio

Advertisement

Bottega Veneta Intrecciato Leather Billfold Wallet
Replace his tired old wallet with this timeless leather style. $460, Mr. Porter.
Courtesy Mr. Porter

Ryland Life Equipment Hank Perfect Cashmere Zip Hoodies
Elevate his loungewear look with this cashmere hoodie. $495, Ryland Life Equipment.
Courtesy Ryland

Johnnie Walker Blue Label Whiskey and Candle
A bottle of Blue Label is already a lovely gift, but take it the next level with this set, which includes a limited edition special candle. $299, Reserve Bar.
Courtesy Johnnie Walker

Advertisement

Assouline 'Marrakech Flair' Book
Gift him this brightly-colored book so the travel lover in your life can dream of Morocco. $95, Assouline.
Courtesy Assouline

Noonday Collection Leatherwork Dopp Kit
A leather-accented dopp kit to organize his toiletries, and prep for the next getaway—we promise, it'll happen at some point! $68, Noonday Collection.
Courtesy Noonday Collection

Nike Air Max 270 Sneaker
An all-black sneaker to replace his boring old athletic shoes. $150, Nordstrom.
Courtesy Nordstrom

Advertisement

Lumin Skin Classic Maintenance Set
This skincare brand is specially formulated for men, for just the right amount of hydration and cleansing. This set comes with a cleanser, moisturizer and exfoliator. $48, Lumin Skin.
Courtesy Lumin Skin

Ralph Lauren Customizable Packable Jacket
This jacket is totally customizable, so you can show just how well you know him. $275, Ralph Lauren.
Courtesy Ralph Lauren

Serengeti Lenwood Sunglasses
He'll wear these sunglasses year-round. $290, Serengeti.
Courtesy Serengeti

Advertisement

Lafco Holiday Frosted Pine and Winter Currant Candle Set
He'll get right into the holiday mood when he lights these cozy candles. $80, Lafco.
Courtesy Lafco

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Finding the perfect gift for the most dapper guy you know might be tricky, but it’s not an impossible task. At least, not anymore, because we’ve found the best presents that even the pickiest man with the most discerning taste will truly appreciate.

Subscribe to Observer’s Lifestyle Newsletter

If you’re searching for a fashionable and unique gift for the guy who loves luxury (whether it’s for your dad, boyfriend, husband, brother or any other of the debonair men in your life), we’ve got the answer to all your holiday shopping woes. From a custom jacket and chic e-bike to cashmere sweaters and indulgent leather accessories, here’s what to buy the most stylish man you know.

Loro Piana Cable Knit BeanieThe most dapper man knows you can't beat Loro Piana, and he'll adore this deliciously soft cashmere beanie. $475, Mr. Porter.

Desmond and Dempsey Corduroy Palm Tree SlippersThese cozy palm tree-embroidered slippers are like a tropical vacation for his feet. $91, Desmond and Dempsey.

Parachute Men's Waffle Lounge Set Guys like matching lounge sets, too, like this ultra-comfy waffle cotton jogger ensemble. $149, Parachute.

Byredo Tobacco Mandarin Perfume Byredo's latest edition to its Night Veils collection is unbelievably good. The fragrance is just the right amount of citrusy and spicy. $330, Byredo.

Orlebar Brown Bulldog Sicilian Summer Mid-Length Swim ShortsA trip to Italy might be out of the question, but he'll love these cheerful swimming trunks, with a print of the Belmond Villa Sant'Andrea in Sicily, as a nice holiday alternative. $345, Orlebar Brown.

Courant Catch:3 Accessory Tray Upgrade his WFH set-up with this leather accessory, which charges all his devices and helps organize all his extra knick knacks. $175, Courant.

Man Crates Whiskey Appreciation CrateYour favorite whiskey connoisseur will love this customizable gift set, complete with a decanter, glasses, ice molds, coasters, a journal and even salted treats. $159, Man Crates.

Bespoke Post Gift Cards [SPONSORED]Bespoke Post is a monthly membership club delivering high-quality and seriously unique goods — from home and bar to outdoor gear, style picks, and more. Give the gift of a gift card worth the value of 1, 3, 6 or 12 boxes. $55 and up, Bespoke Post.

Bruush Electric ToothbrushYou might not think of oral care as the most exciting of gifts, but we promise he'll love this sleek electric toothbrush, complete with six cleaning modes and a timer that tells you when to start brushing a different tooth area. $95, Bruush.

Gucci Brixton Horsebit Collapsible-Heel Leather LoafersYou can't go wrong with a pair of these classic leather loafers. $730, Mr. Porter.

Skyline Chess London Marble and Acrylic Chess SetEven if he's not exactly a chessmaster, he'll still enjoy this marble and acrylic set. $295, Mr. Porter.

Banana Republic Cable Knit Scarf A stylish and simple cable knit scarf he'll wear all the time. $80, Banana Republic.

Truff White Truffle Hot Sauce Before you write off truffle-infused foods, we highly recommend testing out this hot sauce. $34.99, Truff.

La Maison du Chocolat Holiday Cracker Advent CalendarThis indulgent 24-treat gift is perfect for the chocoholic. $70, La Maison du Chocolat.

Eberjey William PJ SetThe debonair man knows that super-soft matching PJ sets are the only acceptable sleepwear. $158, Eberjey.

Edward Field Passport HolderA leather passport case to prep for his next adventure. $97, Edward Field.

Bluejay Premiere Edition BikeThis eco-friendly (and very chic) e-bike comes with a fancy motor, very long-lasting battery and is Gwyneth Paltrow-approved. Even if he's not Goop's biggest fan, he'll still love his new e-bike. $2,995, Bluejay Bikes.

The Art of Shaving Heated Razor With Sandalwood Shaving BundleTreat him to an indulgent shaving kit. This set includes a heated razor, pre-shave oil, shaving cream and balm, in a lovely sandalwood scent. $300, The Art of Shaving.

Vuori Seaside Hoodie An extra-comfy hoodie that's just as useful for a workout as it is for lounging around the house. $118, Vuori.

Theory Quilted GlovesThe most fashionable guy you know will love these quilted leather gloves. $195, Theory.

Away Aluminum Carry-On SuitcaseUpgrade his luggage situation with this special aluminum-edition carry-on from Away. $475, Away.

Clase Azul Anejo TequilaThe tequila lover will adore this incredibly luxe gift, complete with a patterned bottle that depicts the evolution of agave. $500, Drizly.

Madewell Quilted Shirt JacketGift him the perfect in-between-season jacket, for those days when he needs something to throw on over a sweater. $148, Madewell.

Bleusalt The Casa Pant This comfy pant was designed for Cindy Crawford's husband, Casamigos co-founder Rande Gerber, so you already know it's supermodel-approved. $185, Bleusalt.

Maison Francis Kurkdjian Fragrance Wardrobe 8-Piece Discovery Collection For HimCan't decide what scent he'll love? You can't go wrong with this eight-piece set, so he can try out a few different fragrances. $275, Saks Fifth Avenue.

Theragun Elite Percussive Therapy DeviceElevate his workout routine with this Theragun, which helps to ease tension and soreness after just a few short minutes of use each day. $399, Nordstrom.

PopSockets PopWallet+ in Vegan Black Leather The guy who hates carrying around a big wallet will definitely appreciate this tech gadget. $30, PopSockets.

Carmina Norwegian Boots in Brown SuedeThese beautiful suede boots, made by a fourth-generation family of Mallorca-based shoemakers, are sure to be a hit with the most stylish guy. They're classic but still on-trend, and so well-made. $555, Carmina Shoemaker.

Blenders Smooth Arrival Aura Snow GogglesHe'll be the most fashionable skier on the slopes with these new goggles, complete with anti-fog technology. $95, Blenders.

Nordstrom Four-Pack MasksMasks might be the most crucial accessory at the moment (seriously, wear a mask!), so he'll definitely appreciate this addition to his collection, with four comfortable new styles. $20, Nordstrom.

Lord Jones CBD All-Natural Sugarplum Holiday GumdropsA very seasonal treat that combines the best of a classic candy gummy with CBD. $50, Lord Jones.

Five Two by Food52 Essential Cookware 11-Piece SetHe'll feel like a true chef with this shiny new 11-piece cooking set, complete with skillets, pots and pans, all fit for a culinary star. $429, Nordstrom.

Debut Carbon EVO TurntableA glossy black turntable for your favorite music enthusiast. $499, Pro-Ject Audio.

Bottega Veneta Intrecciato Leather Billfold WalletReplace his tired old wallet with this timeless leather style. $460, Mr. Porter.

Ryland Life Equipment Hank Perfect Cashmere Zip HoodiesElevate his loungewear look with this cashmere hoodie. $495, Ryland Life Equipment.

Johnnie Walker Blue Label Whiskey and CandleA bottle of Blue Label is already a lovely gift, but take it the next level with this set, which includes a limited edition special candle. $299, Reserve Bar.

Assouline 'Marrakech Flair' BookGift him this brightly-colored book so the travel lover in your life can dream of Morocco. $95, Assouline.

Noonday Collection Leatherwork Dopp KitA leather-accented dopp kit to organize his toiletries, and prep for the next getaway—we promise, it'll happen at some point! $68, Noonday Collection.

Nike Air Max 270 SneakerAn all-black sneaker to replace his boring old athletic shoes. $150, Nordstrom.

Lumin Skin Classic Maintenance SetThis skincare brand is specially formulated for men, for just the right amount of hydration and cleansing. This set comes with a cleanser, moisturizer and exfoliator. $48, Lumin Skin.

Ralph Lauren Customizable Packable JacketThis jacket is totally customizable, so you can show just how well you know him. $275, Ralph Lauren.

Serengeti Lenwood SunglassesHe'll wear these sunglasses year-round. $290, Serengeti.

Lafco Holiday Frosted Pine and Winter Currant Candle SetHe'll get right into the holiday mood when he lights these cozy candles. $80, Lafco.

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Loro Piana Cable Knit Beanie
The most dapper man knows you can't beat Loro Piana, and he'll adore this deliciously soft cashmere beanie. $475, Mr. Porter.

Desmond and Dempsey Corduroy Palm Tree Slippers
These cozy palm tree-embroidered slippers are like a tropical vacation for his feet. $91, Desmond and Dempsey.

Parachute Men's Waffle Lounge Set
Guys like matching lounge sets, too, like this ultra-comfy waffle cotton jogger ensemble. $149, Parachute.

Byredo Tobacco Mandarin Perfume
Byredo's latest edition to its Night Veils collection is unbelievably good. The fragrance is just the right amount of citrusy and spicy. $330, Byredo.

Orlebar Brown Bulldog Sicilian Summer Mid-Length Swim Shorts
A trip to Italy might be out of the question, but he'll love these cheerful swimming trunks, with a print of the Belmond Villa Sant'Andrea in Sicily, as a nice holiday alternative. $345, Orlebar Brown.

Courant Catch:3 Accessory Tray
Upgrade his WFH set-up with this leather accessory, which charges all his devices and helps organize all his extra knick knacks. $175, Courant.

Man Crates Whiskey Appreciation Crate
Your favorite whiskey connoisseur will love this customizable gift set, complete with a decanter, glasses, ice molds, coasters, a journal and even salted treats. $159, Man Crates.

Bruush Electric Toothbrush
You might not think of oral care as the most exciting of gifts, but we promise he'll love this sleek electric toothbrush, complete with six cleaning modes and a timer that tells you when to start brushing a different tooth area. $95, Bruush.

Gucci Brixton Horsebit Collapsible-Heel Leather Loafers
You can't go wrong with a pair of these classic leather loafers. $730, Mr. Porter.

Skyline Chess London Marble and Acrylic Chess Set
Even if he's not exactly a chessmaster, he'll still enjoy this marble and acrylic set. $295, Mr. Porter.

Banana Republic Cable Knit Scarf
A stylish and simple cable knit scarf he'll wear all the time. $80, Banana Republic.

Truff White Truffle Hot Sauce
Before you write off truffle-infused foods, we highly recommend testing out this hot sauce. $34.99, Truff.

La Maison du Chocolat Holiday Cracker Advent Calendar
This indulgent 24-treat gift is perfect for the chocoholic. $70, La Maison du Chocolat.

Eberjey William PJ Set
The debonair man knows that super-soft matching PJ sets are the only acceptable sleepwear. $158, Eberjey.

Edward Field Passport Holder
A leather passport case to prep for his next adventure. $97, Edward Field.

Bluejay Premiere Edition Bike
This eco-friendly (and very chic) e-bike comes with a fancy motor, very long-lasting battery and is Gwyneth Paltrow-approved. Even if he's not Goop's biggest fan, he'll still love his new e-bike. $2,995, Bluejay Bikes.

The Art of Shaving Heated Razor With Sandalwood Shaving Bundle
Treat him to an indulgent shaving kit. This set includes a heated razor, pre-shave oil, shaving cream and balm, in a lovely sandalwood scent. $300, The Art of Shaving.

Vuori Seaside Hoodie
An extra-comfy hoodie that's just as useful for a workout as it is for lounging around the house. $118, Vuori.

Theory Quilted Gloves
The most fashionable guy you know will love these quilted leather gloves. $195, Theory.

Away Aluminum Carry-On Suitcase
Upgrade his luggage situation with this special aluminum-edition carry-on from Away. $475, Away.

Clase Azul Anejo Tequila
The tequila lover will adore this incredibly luxe gift, complete with a patterned bottle that depicts the evolution of agave. $500, Drizly.

Madewell Quilted Shirt Jacket
Gift him the perfect in-between-season jacket, for those days when he needs something to throw on over a sweater. $148, Madewell.

Bleusalt The Casa Pant
This comfy pant was designed for Cindy Crawford's husband, Casamigos co-founder Rande Gerber, so you already know it's supermodel-approved. $185, Bleusalt.

Maison Francis Kurkdjian Fragrance Wardrobe 8-Piece Discovery Collection For Him
Can't decide what scent he'll love? You can't go wrong with this eight-piece set, so he can try out a few different fragrances. $275, Saks Fifth Avenue.

Theragun Elite Percussive Therapy Device
Elevate his workout routine with this Theragun, which helps to ease tension and soreness after just a few short minutes of use each day. $399, Nordstrom.

PopSockets PopWallet+ in Vegan Black Leather
The guy who hates carrying around a big wallet will definitely appreciate this tech gadget. $30, PopSockets.

Carmina Norwegian Boots in Brown Suede
These beautiful suede boots, made by a fourth-generation family of Mallorca-based shoemakers, are sure to be a hit with the most stylish guy. They're classic but still on-trend, and so well-made. $555, Carmina Shoemaker.

Blenders Smooth Arrival Aura Snow Goggles
He'll be the most fashionable skier on the slopes with these new goggles, complete with anti-fog technology. $95, Blenders.

Nordstrom Four-Pack Masks
Masks might be the most crucial accessory at the moment (seriously, wear a mask!), so he'll definitely appreciate this addition to his collection, with four comfortable new styles. $20, Nordstrom.

Lord Jones CBD All-Natural Sugarplum Holiday Gumdrops
A very seasonal treat that combines the best of a classic candy gummy with CBD. $50, Lord Jones.

Five Two by Food52 Essential Cookware 11-Piece Set
He'll feel like a true chef with this shiny new 11-piece cooking set, complete with skillets, pots and pans, all fit for a culinary star. $429, Nordstrom.

Debut Carbon EVO Turntable
A glossy black turntable for your favorite music enthusiast. $499, Pro-Ject Audio.

Bottega Veneta Intrecciato Leather Billfold Wallet
Replace his tired old wallet with this timeless leather style. $460, Mr. Porter.

Ryland Life Equipment Hank Perfect Cashmere Zip Hoodies
Elevate his loungewear look with this cashmere hoodie. $495, Ryland Life Equipment.

Johnnie Walker Blue Label Whiskey and Candle
A bottle of Blue Label is already a lovely gift, but take it the next level with this set, which includes a limited edition special candle. $299, Reserve Bar.

Assouline 'Marrakech Flair' Book
Gift him this brightly-colored book so the travel lover in your life can dream of Morocco. $95, Assouline.

Noonday Collection Leatherwork Dopp Kit
A leather-accented dopp kit to organize his toiletries, and prep for the next getaway—we promise, it'll happen at some point! $68, Noonday Collection.

Nike Air Max 270 Sneaker
An all-black sneaker to replace his boring old athletic shoes. $150, Nordstrom.

Lumin Skin Classic Maintenance Set
This skincare brand is specially formulated for men, for just the right amount of hydration and cleansing. This set comes with a cleanser, moisturizer and exfoliator. $48, Lumin Skin.

Ralph Lauren Customizable Packable Jacket
This jacket is totally customizable, so you can show just how well you know him. $275, Ralph Lauren.

Serengeti Lenwood Sunglasses
He'll wear these sunglasses year-round. $290, Serengeti.

Lafco Holiday Frosted Pine and Winter Currant Candle Set
He'll get right into the holiday mood when he lights these cozy candles. $80, Lafco.