A Gent’s Guide to “Holidating”in New York

Holidays + dating = holidating. You get it.

A Gent’s Guide to “Holidating”in New York

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This just in: the holiday season tends to be a stressful one. Presents, parties, family drama … long story short, it’s very easy to get swept up in the anxiety of it all and forget to, you know, enjoy it.

Particularly when it comes to your dating life, as the holidays invariably usher in a wide variety of seasonal activations that make for a fun, romantic and memorable excursion with your special somebody.

And thus we’ve partnered with our friends at TAG Heuer to provide you with a couple foolproof itineraries for “holidating,” one right here in the city and the other a little further afield for a (welcome) getaway — both, of course, featuring a dapper ensemble to help you look your best out there.

Go forth and date in good cheer.

Itinerary One: For the City Mouse

This one’s all about dressing to the (creative) nines, enjoying some unexpectedly titillating ballet, and enjoying an impromptu holiday staycation. To wit:

Step One: Your Getup

Getting extra dressed up for a date really amplifies the sense of occasion, and this time of year presents the perfect opportunity. Give a little “holiday black tie” a try: grab yourself a bottle green blazer (this will also prove useful on the holiday party circuit), pair it with your favorite black trousers and a pair of shiny dress kicks, trade the regular tie for a bow, and then cap it all off with socks and a timepiece that add a bit of punch.

Holiday dating outfit urban dress

Jacket by J.Crew, $298
Tie by The Tie Bar, $22
Pocket Square by The Tie Bar, $10
Pants by Bonobos, $198
Shoes by Paul Evans, $395
Socks by Thunders Love, $39
Watch by TAG Heuer, $5,500

Your Timepiece:


When your ensemble is this churched up, you want some wrist hardware that fits the proceedings. Enter the TAG Heuer Carrera Calibre Heuer 02 chronograph, a handsome fine-brushed and polished steel number with a bold black ceramic bezel and skeleton dial sure to turn a few heads. Red accents via the subdial and second hands for a little yuletide flair? That’s pure holiday gravy.

Step Two: Tchaikovsky, But Make it Sexy

Perhaps no other piece of holiday fantasy is quite as beloved as The Nutcracker, and only New York could deliver an interpretation quite as off the wall dazzling as Company XIV’s Nutcracker Rouge. Former Met Opera choreographer and company founder Austin McCormick has assembled a glorious cabal of opera singers, aerialists, circus performers and burlesque artists to give Tchaikovsky’s classic a delightfully hedonistic, tassel-twirling spin that honors the original while simultaneously mixing in contemporary tunes, ribald humor and a very French cabaret vibe.


Step Three: Nightcap in the Sky


A proper holiday night on the town deserves to be closed out in style, and that means a nightcap to remember and a stay in a bed other than your own. Being the savvy individual that you are, you’ll have booked a surprise overnight stay at The Dream Hotel Midtown, where they’ve transformed their rooftop PHD Terrace into “A Midwinter Night’s Dream” — featuring thousands of hanging twinkle lights and floral installations as well as a “tunnel of lights” built specifically for ‘gram-worthy photos, it’s the perfect spot to wind down, enjoy a delicious seasonal cocktail and snap a couple pics to remember your evening by before adjourning to your room. Congrats, this date will now be talked about for years to come.

Dream Hotel New York Midwinter Night's Dream PHD Terrace


Itinerary Two: For the Country Mouse

Those of you looking for a brief respite from NYC holiday craziness, fear not. We’ve got you covered on a close-but-not-too-close jaunt featuring some good old fashioned (but sustainable!) tree cutting and cozy mountain digs. To wit:

Step One: Your Getup

This is where rugged meets refined — you want a getup that’ll do you justice out in the the woods, but also carry you right into dinner if the need arises. You’ll want a pair of boots that deftly tread the line between brawny and dapper, and flannel-lined canvas pants of that same ilk. Up top it’s all about handsome layers, and nobody ever went wrong with a flannel/vest/quilted jacket trifecta. Knit beanie and sporty timepiece to complete the look.

holiday dating guide outfit country new york

Boots by L.L. Bean, $199
Pants by Wrangler, $54
Shirt by Todd Snyder, $178
Vest by Taylor Stitch, $138
Jacket by Barbour, $150
Beanie by American Trench, $35
Watch by TAG Heuer, $5,900

tag heuer monaco watch

Your Timepiece:


Finding the right watch for a kit like this is a tricky proposition. You want something sporty enough that it doesn’t seem out of place with a more casual ensemble, but elegant enough that it’s helping to elevate the overall vibe. Look no further than the TAG Heuer Monaco Calibre 11, created by Jack Heuer in 1969 and made famous by King of Cool Steve McQueen in the film Le Mans. The iconic square case, blue dial and perforated calfskin strap (reminiscent of driving gloves) lend the Monaco a left-of-center versatility that works perfectly in situations like these.

Step Two: Get Thee a Tree

An hour north of the city just outside the sleepy hamlet of Warwick, NY, you’ll find Emmerich Tree Farm, family-run since the ’60s and proffering enough varieties of sustainably-planted spruces, firs and pines to satisfy even the pickiest tree grinch. You’ll take a wagon ride out to the fields to cut your tree before adjourning back to the farm’s pavillion for holiday tunes, hot cocoa and a roaring bonfire. Emmerich’s staff will help you load up your holiday haul and you’re good to go.

Emmerich Tree Farm New Jersey


Step Three: Weekend Winter Wonderland


A short jaunt across the border into Jersey lies Crystal Springs Resort, a sprawling complex nestled at the foot of the Kittatinny Mountain Range featuring two gorgeously appointed hotels (with accompanying luxury spa facilities) and all manner of wintertime distractions. From horseback riding on snowy trails to marshmallow roasting ’round the campfire to lounging in outdoor jacuzzis with views of the surrounding peaks, this is the perfect place to recharge before heading back into the NYC holiday fray.

Crystal Springs Resort New Jersey

For those of you who happen to be bi-coastal, we’ve also got some killer holidating plans for Los Angeles — step right this way to check them out.