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12 Guys of Christmas: The Dapper Man

36 gift ideas for the stylish man

Nothing sets the teeth to rattling like the task of gift buying for a style zealot (except maybe an in-law’s icy glare). Rolled or cuffed? four-in-hand or windsor? Double breasted or single? Brown or black? Personal style is, well, personal; a faux pas can have lasting consequences.

That’s why we’re throwing you a life line: 36 stylish picks in 12 style mainstays that should all strike a chord with the handsome man (you, of course) in your life. From show stoppers to the little things that make a big difference, all of these wardrobe staples are accessible to just about every man’s fashion sense. Take a deep breath, struggle desperately to remember what you last saw in their closet, and read on.

Looking for more men’s gift guides? Check out all our gift guides for men this way.

1. Chukka Boots


Fun fact to calm your tense, gift-finding nerves: Chukkas are named after the two halves of a polo game. Luckily, they’re not reserved for rich Brits. These ankle-length boots are the perfect footwear solution: they work dressed up or down, and are perfect for maintaining comfort without roasting your feet in hot weather or freezing them when it’s cold. Whether they’re rugged or classic (or, very reasonably, both), they’re a fantastic footwear mainstay.

Our Suggestions: 1. Clarks Desert Boots $120 | 2. Cole Haan Lunargrand $298 | 3. Red Wing Postman Chukka $240

2. Scarves


It’s way beyond the ugly pythons Grandma used to knit for you. Let those go. A scarf isn’t just for old people in the winter, and it’s not just a hipster’s go-to accessory, either. With the right jacket or sweater, this neckwear can be a well-dressed man’s coup de grace.

Our Suggestions: 1. Drakes Polka-Dot $113 | 2. Burberry Brit Light Gray Icon Check Cashmere $395 | 3. Alexander Olch Solid $109

3. Quality Denim


Jeans are the vanilla ice cream of men’s wear — it’s hard not to blend in while sporting them. But face it: Wranglers don’t get you laid, no matter how much they emphasize your crotch. The right pair will fit like a glove, and there’s even some great bespoke companies out there for the true perfectionist with a trust fund to burn.

Our Suggestions: 1. 3×1 Bespoke $1200+ | 2. Imogene + Willie $198+ | 3. Levi’s 501 Original Fit Made in the USA Waterless $178

4. Suits


Buying a suit feels like a daunting task, but the payoff is worth the risk. With the right measurements and a good eye for a sharp fit (one that your Grandpa, or your dad — since it isn’t powder blue — wouldn’t approve of) you’re well on your way. A sharp suit inspires confidence and always come through clutch on important occasions — and for super fancy occasions, you can’t beat a tux.

Our Suggestions: 1. Suitsupply Roma Brown Plain $469 | 2. Brioni Grosgrain-Trimmed Wool Tuxedo $6,995 | 3. J. Crew Ludlow $500+

5. iPhone Cases


Quick: what do you check more, your watch or your iPhone? Would you trade it for your belt? Your socks? Hell, would you give it up for your favorite pair of shoes? If you answered the way we think you did, then why the hell is your most treasured item dressed in cheap plastic? Otter Boxes might work for Bear Grylls, but there are more sophisticated options that won’t turn your phone into a casket.

Our Suggestions: 1. J. Crew Leather iPhone 5 Case $38 | Makr iPhone 5 Sleeve Navy Matter $95 | 3. Killspencer iPhone 5 Alcantara Midnight Black Veil Back $25

6. Trench Coats


The trench coat has had some bad ambassadors (Neo, Pedos and Columbo) — but it’s still a classic style staple. Today’s water-repellent synthetics are great, but you shouldn’t look like you’re summiting K2 on your next swanky dinner outing in inclement weather, either. Oh look, something that’s both stylish and utilitarian. What a novel idea.

Our Suggestions: 1. Gap Double-Button $118 | 2. Mackintosh Dunoon Handmade Bonded-Cotton Rain Coat $291 | 3. Nau Down Tempo Trench $500

7. Watch Straps


Strapped for ideas (see what we did there)? This one’s easy: every guy’s got a watch, and could use a great new strap. It’ll help him get more mileage out of his favorite timepiece by mixing up the look.

Our Suggestions: 1. Hirsch Viscount Alligator $375 | 2. The Knottery Solid Color Nylon $10 | 3. Hodinkee Camouflage Suede $165

8. Style Books


If he isn’t well read, you’re not searching on this website for his gift. Yes, style can be learned, and even the most savvy guy can be better informed. Humorous, insightful, interesting: sartorial publications are the perfect home library addition.

Our Suggestions: 1. Take Ivy $17 | 2. Dressing the Man: Mastering the Art of Permanent Fashion $38 | 3. Fuck Yeah Menswear: Bespoke Knowledge for the Crispy Gentleman $15

9. Dress Shirts


If I guy declines a new dress shirt, tell him to take a long hard look at his sweat-stained collar. Guys need these. If you got Prince his millionth frilly shirt, he’d still be frilled thrilled. From non-iron to bespoke to vintage, they’re all right in the style wheelhouse.

Our Suggestions: Hamilton 1883 Classic Collection $245 | Brooks Brothers Non-Iron Slim Fit $88 | Outlier Northeast Pivot Shirt $98

10. Pocket Squares


This ain’t for wiping your nose. A good pocket square makes a suit; it also turns heads. The best part? Rumpled and “casual” is just as much of a statement as perfectly folded. Remind him to refrain from waving it wildly when he gets excited — it’s a tempting, fatal man mistake.

Our Suggestions:1. Chief Two-Pack Patterned $22 | 2. MS & Co. Three Pack Silk Knit $95 | 3. The Hill-Side Selvedge $44

11. Sneakers


As much as we cover them for marathoners that could sprint to the supermarket and back in the time it takes you to lace up, these everyday pieces of foot gear, so often pigeonholed into “sport tech” or “humble”, can also be part of a stylish, laid-back look. You want to look presentable, even in sweats and a long sleeve t-shirt — that’s what really sets apart the true style master, anyway.

Our Suggestions: 1. Nike Roshe Run $94 | 2. Tretorn Nylite Canvas $65 | 3. Converse Jack Purcell $60

12. Sweaters


You’ve spouted to your shrink about how much those horrid knitted monstrosities destroyed Christmas for you as a child. Now take back the sweater, and take back your dignity. There’s some sharp, extremely affordable options out there, whether they be quarter zips, V-necks or the ever present cashmere comfort cruiser. Layering’s never felt so good.

Our Suggestions: 1. Paul Smith Jeans Dotted $221 | 2. J. Crew Donegal Cardigan $128 | Ralph Lauren Cashmere V-Neck $278

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