The Guy's Guide To Holiday Dressing

As much as a great girlfriend or discriminating eye can lend a helpful sartorial hand, there's no doubt about it: Dressing up after-dark for guys can be utterly stressful. Go too subtle and you end up on the dullsville casual side…or go too festive and feel paranoid all night that everyone's secretly snickering at your tartan cumberbund. Well, whether you're a guy with a full holiday dance-card or his best girl hoping for a little Mad Men role play, we've got 6 snazzy outfits sported by some super-cute fellas who show us how to make holiday dressing work whatever your vibe may be.
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The New Classic
Name: Philippe von Borries
Occupation: Co-Founder, Refinery29
Holiday plans: "Maine for Christmas and then a birthday bash with my grandfather for his 100th birthday!!!!"
What you want most this holiday: "Fun, friends, and family. Santa can reference my wish-list here."
Your holiday dress-up MO: "You can't go wrong with classic if you wear it in your own way."
Signature dress-up essential: "Quality old-school accessories like a good knit tie and maybe a new Breitling watch for good luck."
What You're Wearing: A Zegna jacket, Rag & Bone shirt and pants, Steven Alan tie, and NDC boots.
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The Playful Prepster
Name: Kristian Laliberte
Occupation: "New York editor for Refinery29."
Holiday plans: "Absolutely nothing, which is making me so, so happy. I'm just going home to Nahant to spend some major QT with my family. My mom goes all-out for Christmas, meaning lots of mulled apple cider, gingerbread, carols....I can't wait to eat, pray, and love."
What you want most this holiday: "More drive to get up and go to the gym. A Mac Air. An awesome snow-proof coat that actually looks cool. Oversized Wayfarers. A bigger apartment."
Your holiday dress-up MO: "I like to mix and match prints. Plaid on plaid always rocks. A tuxedo jacket, cozy shawl collar sweater, tweed pants, and a soft-button down pretty much makes up my pre-Christmas parties outfit DNA."
Signature dress-up essential: "A bow-tie is an easy way to amp up a flannel and jeans."
What You're Wearing: "Ralph Lauren wool-cashmere coat, Ben Shermanshirt, Gansevoort Tailor by Buckler tuxedo pants, Original Penguin bow tie, vintage Sergio Rossi shoes, and a Tod's My Colors leather bracelet."
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The Edgy Academic
Name: Brian Jeffers
Occupation: "Design associate at Refinery29."
Holiday plans: "Going back to Ireland to see my family and friends. I am especially looking forward to petting my dog, watching the TV show 'Misfits,' petting my dog some more, seeing my two little nephews. and sleeping till noon."
What you want most this holiday: "I just want to eat, drink and be generally merry. Although I won't say no to an iPad..... or a pair of snow boots, but the iPad would be preferable."
Your holiday dress-up MO: "To add a splash of color. Adding something bright and festive to my outfit gets me in the holiday mood. That and drinking too many hot whiskeys with friends."
Signature dress-up item or essential: "I do love a patterned holiday sweater or a wooly bobble hat. They have been my holiday essentials since my mother put me into them as a child, and now I keep up her tradition."
What You're Wearing:"A Vince sweater, Acne jeans, and Tod's Esquire Boots."
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The Downtown Dandy
Name: Steven Rojas
Occupation: "Director of Social Media for the Grand Hotels."
Holiday plans: "I plan on spending the holidays with my family and learning how to ice climb. For some much-needed downtime, I love relaxing by the fireplace at the Soho Grand's clubroom."
What you want most this holiday: "For people to reach into their hearts and donate money to the Scleroderma foundation. Scleroderma is a chronic systemic autoimmune disease. This is first time I have ever mentioned this publicly, but in 2008 my mother was diagnosed with Scleroderma. Due to the rarity of such a disease, there is a lack of funding and many people pass away because of it. I hope that this holiday people donate time or money to help those in need."
Your holiday dress-up MO: "Suits! I love a nice warm tweed suit for all of my holiday parties."
Signature dress-up essential: "The perfect blazer. My favorites are from A.P.C. and Surface to Air."
What You're Wearing: A Topman suit, Ralph Lauren shirt, J. Crew tie and socks, Surface to Air shoes, Duncan Quinn pocket square, and a vintage Rolex watch.
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The Modern Marlon Brando
Name: Dino Siampos
Occupation: "One half of Aux Armes Etc."
Holiday plans: "Home for the holidays. Cold Chi-town."
What you want most this holiday: "More laughter."
Your holiday dress-up MO: "Mistletoe at the end of a fishing pole."
Signature dress-up essential: "Slicked-back groomed hair, freshly trimmed from Freemans Barber Shop and shiny new polished dress shoes."

What You're Wearing: A Tommy boat shirt, Helmut Lang jeans, Thom Browne boots, Randolph sunglasses, and a 1951 Omega watch.
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The Vintage Gentleman
Name: Sam Wheeler
Occupation: "Retail genius, one-half of Aux Armes."
Holiday plans: "I'm headed to Miami with my wife Shira and my new In-laws."
What you want most this holiday: "World peace, of course. And an old Gibson SG."
Your holiday dress-up MO: "Dirty-dandy-meets-Animal-House."
Signature dress-up essential: "A '60s check Ivy League jacket by Sears."
What You're Wearing: A Dries van Noten jacket, Tommy sweater, Thom Browne shirt, Onassis pants, and a vintage tie and pocket square.
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