BEST OF: WINTER DATE IDEAS IN NYC

Winter Date Ideas in NYC - What to Wear and Where to Go

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).

Winter Date Ideas in NYC - What to Wear and Where to Go

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. Star Gaze – Twice a month (weather permitting) Columbia University opens their observatory for star-gazing. Is there anything more romantic?
  8. 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.
  9. Comfort Food – Winter is perfect for getting your comfort food on. We love S’mac, Ivan Ramen, Meatball Shop, orĀ Spaghetti Incident for a hearty meal that’s an alternative to take-out when it’s cold.
  10. 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.
  11. 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.
  12. 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.
  13. 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.
  14. 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.
  15. 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.

Winter Date Ideas in NYC - What to Wear and Where to Go

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.

WINTER DATE NIGHT LOOK:

Winter Date Ideas in NYC - What to Wear and Where to Go Winter Date Ideas in NYC - What to Wear and Where to Go

 

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4 CASUAL HOLIDAY OUTFIT IDEAS

The Steele Maiden: Casual Holiday Outfit Ideas - denim, sweaters, blazers and vests

If it’s any indication what November was like at work for me – know that I shot all of these looks over the past month and am only now getting the chance to find time to post them (I’m ready for you Christmas break!). In any case, now that I’m ready I figured I’d compile them since they all have a bit of a common theme – festive yet comfortable. Below, a closer look at these casual holiday outfit ideas:

The Steele Maiden: Casual Holiday Outfit Ideas - red sweater and boyfriend jeans

I picked up this oversizedĀ red sweater during Black Friday sales and honestly can’t stop wearing it. I’ve dressed it up with heels and a skirt for work, but I like it with boyfriend jeans, fancy flats and a fisherman’s cap too for holiday shopping or weekend errands this month.

SHOP THE LOOK:

The Steele Maiden: Casual Holiday Outfit Ideas - red sweater and boyfriend jeans The Steele Maiden: Casual Holiday Outfit Ideas - red sweater and boyfriend jeans The Steele Maiden: Casual Holiday Outfit Ideas - overalls and metallic sweater

It’s been awhile since I last pulled out my overalls but I quickly remembered why they’re my favorites (spoiler: SO comfy). Dressed them up a bit with this metallic striped sweater and metallic kitten heels and this outfit made going to the grocery store for cookie baking supplies all the more merry.

SHOP THE LOOK:

The Steele Maiden: Casual Holiday Outfit Ideas - overalls and metallic sweater The Steele Maiden: Casual Holiday Outfit Ideas - plaid puffer vest and sneakers

I’m calling this my tree-trimming outfit. I love a good puffer vest in the winter – and all the better if it’s in tartan plaid – and I’ve been wearing these sneakers non-stop lately. I spend a lot of time in heels, but sometimes you just can’t beat a pair of comfy kicks. The olive green feels a little Christmas-y too which I love.

SHOP THE LOOK:

The Steele Maiden: Casual Holiday Outfit Ideas - plaid puffer vest and sneakers The Steele Maiden: Casual Holiday Outfit Ideas - plaid puffer vest and sneakers The Steele Maiden: Casual Holiday Outfit Ideas - velvet blazer and plaid heels

This one is a little bit unexpected, but no less festive in my opinion. I like mixing in colors like bright gold or deep navy blue to holiday style and this velvet blazer and plaid heels are just the ticket. Mixed with fun socks just because.. more is more this time of year, right?

SHOP THE LOOK:

The Steele Maiden: Casual Holiday Outfit Ideas - velvet blazer and plaid heels

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HOLIDAY BEAUTY FAVORITES

The Steele Maiden: Holiday Beauty Favorites for a Night Out

From the lipstick that will stay put even after a glass or two of champagne to the hair product that rids me of winter static – here are my holiday beauty favorites:

P.S. these would make great stocking stuffers too!

SHOP HAIR + SKIN FAVORITES:

SHOP MAKE-UP FAVORITES

Also – can we talk about how luxurious it is to get ready in a large bathroom? If you have one at home I hope you don’t take it for granted for a single second. This particular one is in a suite at the Omni Berkshire – if you’re in to that sort of thing you should enter my giveaway to win a one-night stay here.

The Steele Maiden: Holiday Beauty Favorites for a Night Out

WINTER WORKWEAR WITH MAGGY LONDON

The Steele Maiden: Winter Workwear - Maggy London Red Floral Shift Dress

Earlier in the Fall I polled you guys on Instagram to ask what you wanted to see more of going forward – and one of the standout results was a request for more work-wear. When it comes to office style, I’m lucky to work in a ‘creative casual’ environment. But as my role has grown and I’ve become responsible for running meetings and managing a small team – I’ve started to rely on pieces that lean towards a more polished look.

One of my very favorite office-friendly brands is Maggy London. I first worked with them at the end of the summer here and wore those 3 dresses on repeat through the Fall. So when they came back and asked me to style a few looks that would transition from Fall to Winter I jumped at the chance. Their work dresses always feel feminine without being frilly and office-appropriate without being boring.

You can see all three looks that I styled here and below is this red floral shift dress, my favorite from the three I styled (apparently I’m on a red dress kick lately). I love that it feels festive enough to wear straight out after work for holiday cocktails. Not to mention, seriously flattering.

And lastly, since we’re right in the middle of my 5 days of giveaways – I’m giving away this same dress here. Good luck!

The Steele Maiden: Winter Workwear - Maggy London Red Floral Shift Dress The Steele Maiden: Winter Workwear - Maggy London Red Floral Shift Dress The Steele Maiden: Winter Workwear - Maggy London Red Floral Shift Dress The Steele Maiden: Winter Workwear - Maggy London Red Floral Shift Dress The Steele Maiden: Winter Workwear - Maggy London Red Floral Shift Dress

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HIS AND HERS HOLIDAY STYLE: FOR A SPECIAL OCCASION AT OMNI BERKSHIRE PLACE HOTEL

The Steele Maiden: His and Hers Special Occasion Holiday Style - Red Wrap dress and navy blue suit

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.

SHOP THE STORY

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!

 

The Steele Maiden: His and Hers Special Occasion Holiday Style - Red Wrap dress and navy blue suit

Adam wore a classic slim fit navy blue suit and 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.

On Jess: Express Satin Wrap Dress | J.Crew Star Statement Earrings | Gigi New York Clutch c/o | Tamara Mellon Pistol 105 Pumps c/oĀ 

On Adam: Topman Navy Suit | Ben Sherman Oxfords

The Steele Maiden: Omni Berkshire Place Hotel - NYC at the Holidays The Steele Maiden: His and Hers Special Occasion Holiday Style - Red Wrap dress and navy blue suit The Steele Maiden: His and Hers Special Occasion Holiday Style - Red Wrap dress and navy blue suit The Steele Maiden: Special Occasion Holiday Style - Red Wrap dress and Tamara Mellon Pistol Pumps The Steele Maiden: His and Hers Special Occasion Holiday Style - Red Wrap dress and navy blue suit The Steele Maiden: His and Hers Special Occasion Holiday Style - Red Wrap dress and navy blue suit The Steele Maiden: His and Hers Special Occasion Holiday Style - Red Wrap dress and navy blue suit

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