I get it. It’s cold outside and your Netflix subscription feels like a safe bet. I’m guilty of it too. But don’t let Winter be an excuse to forgo date night. New York (and honestly every place if you get creative) has a million awesome options worth leaving your couch for. Here – my top 15 Winter Date Ideas in NYC plus an outfit idea that is date-friendly but also warm (shivering is not sexy).
Museum Hopping – There’s no shortage of options here but our favorites are the Met for room to roam and the MoMa or Whitney for modern art. Perfect for a freezing cold afternoon.
A Night at the Theater – Going to the ballet is one of my all-time favorite special date nights. Use it as an excuse to get dressed up and head to Lincoln Center.
Go Sledding – Wait for the first big snow and head to Central Park. Even if you don’t actually go sledding, snow ball fights and a long walk through a freshly blanketed park is a pretty memorable day date.
Hot Chocolate Crawl – Skip the bar and hop along a map of the city’s best hot chocolate spots instead. Max Brenner in Union Square, Serendipity on the Upper East Side and City Bakery in Flatiron are all great.
Arcade Challenge – Stock up on quarters and hit up a classic arcade. Go head to head in Pacman, Pinball and the rest while you drink cheap beer. Barcade in the East Village and Two-Bits Arcade in Lower East Side are my favorites.
Grand Central Glamour – Turn back time by taking a trip to Grand Central. Take in the beauty of this classic New York architecture and then grab oysters at the Grand Central Oyster Bar.
Star Gaze – Twice a month (weather permitting) Columbia University opens their observatory for star-gazing. Is there anything more romantic?
Skyline Gaze – If you’d rather stare at the skyline then the stars, then you need to head to the roof. While most aren’t quite as good in the Winter, 230 Fifth has plenty of heaters, cozy blankets and unbeatable views of the Empire State Building. It can get crowded/touristy on weekends and is on the pricey side – but for the views and a drink or two it’s a pretty awesome weeknight date.
Indoor Blooms – While the Brooklyn Botanic Garden is tough to beat in Spring, there are plenty of greenhouses that are worth visiting in Winter too.
Ice-Skating – There are several outdoor rinks in the city but my absolute favorite is Wollman Rink in Central Park. Pro tip – wait for an evening with light snow. Most people don’t think to go but the rink stays open and skating hand in hand while snow falls against the backdrop of the city skyline is pure New York magic.
Catch a Movie – First of all, get MoviePass. It’s only $9.95 for unlimited movies and nearly every theater we go to is included. Including places like NiteHawk in Brooklyn where you can get dinner and drinks while you watch the movie or the Angelika and Film Forum in the city that play awesome independent films.
Find a Fireplace – There are quite a few cozy bars downtown that have a roaring fireplace. Order a hot toddy and snag a seat by the flames. Bowery Hotel in the East Village is a good standby.
Have a Staycation – You all know, I’m all about a hotel staycation in your own city. If it’s not in the budget, you should at least head to a hotel lobby for a drink (case in point: Bowery Hotel in the previous suggestion). They’ve always got great decor and even for a couple of hours, you can feel like you got away. I love Gramercy Park Hotel, Soho Grand and the Standard.
Live Music – There’s honestly amazing live music everywhere in this city, but two of Adam and I’s favorites are Jazz Standard in Gramercy for incredible classic jazz or Arlene’s Grocery for dive bar bands.
And if your next question is great – but what on earth do I wear that works for cold-weather but also looks cute.. I got you. I love these velvet jeggings as an alternative to jeans (that are super warm!), sleek booties that can withstand a bit of slush and aren’t as treacherous as heels on snowy streets, and a big faux fur coat that feels less boring than your everyday parka.
For the past three years, Adam and I have gotten into the habit of taking holiday pictures (in 2015 we searched for Christmas trees and in 2016 we took a ride in a very special ’54 Chevy) – but this year we thought it might be fun to get all dressed up. So we put on our finest – outfits that would be perfect for any holiday special occasion like a night at the theater, New Year’s Eve party or formal wedding – and headed straight for the rooftop of the Omni Berkshire Place hotel.
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This past Summer we had the most amazing staycation at the hotel and ever since then have thought of the Omni Berkshire so fondly. But with the place all dressed up for the holidays? We were floored. So we danced on the rooftop balcony overlooking St. Patrick’s Cathedral, surrounded by skyscrapers. We drank champagne and ran around a fancy suite with our own personal Christmas tree. And we laughed about how two kids from the country ever ended up here, with this crazy life. It was pure holiday magic.
And – because we always want to inspire you all to have stylish adventures of your own – I’m giving one lucky reader the chance to win a one-night stay at the Omni Berkshire (enter via my Instagram – giveaway launching at 9AM today 11/28). Whether you’re a New Yorker looking for a chic staycation or an out of towner dreaming of your own getaway in the big apple, this is your place. Good luck!
Adam wore a classic slim fit navy blue suitand I wore this (under $100!) slinky red satin wrap dress and fun starry night statement earrings. Also – can we take a moment to talk about these shoes? They’re Tamara Mellon (one of the founders of Jimmy Choo who started her own line) and are in the running for the most amazing heels I think I’ve ever worn. If you’re looking for a luxurious splurge for the holidays – I can’t recommend them enough.
Yesterday I styled these velvet jeggings in a way that was simple yet chic for the office or casual holiday parties – but because honestly I just can’t get enough of them and wore them multiple times on our recent travels, I’m back with a more weekend ready alternative.
One of my favorite things about Fall fashion are all the luxe textures. And this outfit from Talbots I wore on our first day in Edinburgh checks off all my favorites. A classic cashmere sweater, velvet jeggings and faux fur vest. Not to mention plaid on plaid (when in Scotland.. do as the Scots do, right?).
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I like that all together it feels simple but because of the mix of rich textures it also feels super chic. It’s exactly the sort of thing I would wear to the office and then straight out afterwards for an event or holiday drinks this season. Plus, the fact that they’re separates means that you could also add any of them to a more casual look to elevate the whole thing. And can we talk about these velvet jeggings?? I know, I felt skeptical at first too but then I tried them on and proceeded to wear them on 3 separate occasions during our 10 day trip. They come in a bunch of colors but I’m loving the ivory color. Tomorrow I’ll be sharing an entirely different way to wear them.
P.S. This area in Edinburgh was called Dean Village and was truly like stepping back in time. Can’t wait to tell you more about our short but sweet time in Scotland.
London calling! As we speak, I’ve made it back to New York and am fighting off a cold and jet lag (no easy feat) – but also am so excited to share with you all the places we went and naturally, all the things I wore. This look is from our first night out in London and one of my favorites from the whole trip.
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We headed to Camden Town (kind of the East Village of London if you will, and where I lived when I studied abroad there for a semester) for a night out and ended up grabbing last minute tickets to London’s Jazz Cafe where they were playing a tribute to Van Morrison’s Astral Weeks album. I’ve been a huge Van Morrison fan since high school so I was hoping they’d do the album justice… and was literally blown away. So good that Adam and I still haven’t stopped talking about it. Then it was a few more drinks, a little dancing and back to our first AirBnB of the trip to collapse into jet lag. For the record I don’t recommend this big of a night for your first day adjusting to a new time zone, but I also don’t regret it one bit.
This leopard ruffle dress (under $40!) and patent booties held up through it all and hopefully helped fit in with the British girls who just always look so effortlessly cool. Also, carried my vintage YSL clutch that is one of my most prized purchases from the vintage markets in Camden Town – bought almost exactly 10 years ago. How’s that for full circle?