A Gent’s Guide to “Holidating”in Los Angeles

Holidays + dating = holidating. You get it.

A Gent’s Guide to “Holidating”in Los Angeles

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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: Downtown Jaunt

This one’s all about looking sharp, engaging in two of the season’s most tried-and-true activities, and enjoying an impromptu holiday staycation. To wit:

Step One: Your Getup

This is gonna be one of those dates that involves both some cozy boozing indoors as well as some walking (and skating) around outside, so you’ll want to be comfy, appropriately layered, and, of course, stylish. Classic jeans and a tee work well when you layer in a lightweight cardigan and top it off with an eye-catching bomber — especially when you add elevated touches like streamlined sneaks and an appropriately sporty timepiece. Holiday socks make for a nice conversation piece when changing into your skates.

los angeles holiday dating style guide

Jacket by Todd Snyder, $998
Sneakers by Greats, $179
Denim by Outerknown, $128
T-Shirt by Goodlife, $60
Cardigan by Uniqlo, $40
Socks by J.Crew, $39
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: Sip n’ Skate

Perhaps no other holiday pastime is quite as beloved (and occasionally feared) as strapping on a pair of skates and taking to the ice — what you’re going to want to do here is head downtown and give yourself a (reasonable) dose of liquid courage before crossing it off the ol’ dating bucket list. The Pershing Square Holiday Ice Rink is back with a slew of live music and special events, and nearby (see: walkable) cocktail haunts Seven Grand and Birds & Bees are both decked out for the season and proffering delicious holiday libations from mulled wine to boozy eggnog. Might we suggest bar-skate-bar?


Step Three: Dinner, Drinks and a Surprise Staycation


A proper holiday night on the town deserves to be finished in style, and that means a dinner/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 NoMad Los Angeles, where you can dine in the glow of their massive tree and the award-winning bar team will once again be hosting their “Holiday Spectacular” cocktail pop-up — the perfect way to close out your evening. Congrats, this date will now be talked about for years to come.

NoMad Hotel Los Angeles


Itinerary Two: Historic Inland Getaway

When someone says “holiday getaway,” Riverside is perhaps not the first location that springs to mind. However, those in the know will tell you that a trip to the 951 will net you one of the most jaw-dropping yuletide spectacles America has to offer (plus a romantic weekend hideaway). To wit:

Step One: Your Getup

So here’s the deal: for an excursion this merry, it’s fun to really look the part. Enter the fair isle sweater, foolproof sartorial signpost of holiday cheer (and also something that will come in handy on the holiday party circuit). Trading in jeans for a nice pair of cords helps to elevate the look, as does a pair of boots that play off the sweater’s tones. A topcoat in place of your standard jacket is a nice finishing touch, and should also protect against temps that can dip into the 40s come nightfall. Don’t forget a handsome watch to keep track of time … you don’t want to miss the fireworks.

los angeles holiday dating style guide

Sweater by J.Crew, $45
Pants by Bonobos, $98
Coat by J.Crew, $278
Boots by Thomas & Vine, $115
Socks by Roots, $22
Watch by TAG Heuer, $5,500

Your Timepiece:


When your ensemble is this festive, 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: All of the Lights

Considering it’s been going for the last 27 years, a shocking number of Angelenos are still unaware of the holiday extravaganza that is the Riverside Festival of Lights. Each year, a team of 20 works round the clock for ten straight weeks to transform the historic Mission Inn into a winter wonderland that must be seen to be believed — adorned with over five million lights, the property also features over 200 characters across the premises, live music, fireworks shows and more. New this year: a four-story cascading light chandelier and the world’s largest mistletoe. If this place doesn’t get you into the spirit, nothing will.

Mission Inn Festival of Lights Riverside CA


Step Three: Your Illustrious Digs


It would be a shame to come all this way and not use it as an excuse for a weekend stay at such a storied property — originally opened as a quaint adobe boarding house in 1876, the Mission Inn Hotel and Spa has blossomed over the years into a grand architectural spectacle that ranks as a National Historic Landmark and has played host to presidents, celebrities and movie shoots. AAA Four Diamond accommodations, an award-winning spa, and some of the most awe-inspiring historic grounds you’re likely to run across make this spot a no-brainer for a romantic night or two (or three) away from the L.A. grind.

Mission Inn Riverside CA

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