Dressing for the Holidays


Aside from the cold – this really is the most magical time of year in New York. The city is decked out in its holiday best, there are lights everywhere and plenty of occasions to pour a glass of bubbly. I can’t get enough. Which is why I wanted to create a holiday bucket list to be sure that I make time to enjoy as much of the season as possible. Some of the things on my list are beloved traditions at this point while some are things we have still yet to experience in New York and really want to get around to doing this year. Also – a reminder that not everything has to be expensive this season – plenty of the things on my list are super budget friendly, if not free!

Ice skating Dates:

Now that Adam and I both own ice skates, we want to take advantage of all of the fun rinks in the city! My favorite is skating in Central Park – with the city in view around you – but Bryant Park and Rockefeller Rink (if you get there super early or on a weeknight) are also great. Budget tip: Bryant Park is actually free to skate at and so are locker rentals if you bring your own lock, so this is a great cheap date idea.

Lights at Dyker Heights:

Remember that one house in your town that used to go all out with lights and yard decorations for the holidays? Dyker Heights is like that.. but x100. A neighborhood in Brooklyn where for about 4 square blocks – every single house is boasting thousands of Christmas lights, and more Santas and snowmen then you have ever seen in one place. We usually pack a “car picnic” and then drive through the neighborhood while listening to holiday tunes. Festive and totally free!

Dinner at Lucien and Minetta Tavern:

There are some restaurants that just really shine in the winter. Cozy and intimate, all candlelight and linen tablecloths, they make braving the cold for date night well worth it. Lucien in the East Village and Minetta Tavern in the West Village have been on our restaurant bucket list for a long time and I’d love to finally try them both this holiday season.

Hot Toddies, Rockefeller Tree + Fifth Avenue Windows:

This has quickly become one of our favorite holiday traditions. We pick a Sunday evening in December, make a big thermos of hot toddies and then head uptown to see the Rockefeller Tree and the windows on Fifth Avenue. Notoriously crowded and often quite cold – we found that the hot toddies really raise your spirits on the trek and ultimately make the whole thing a lot more fun.


It can be easy to get swept up in all of the consumption of the holidays without pausing to think of those that are having a much tougher time. I hate to think of families that are struggling to get a few gifts under the tree for their kids – so this year, Adam and I starting the yearly tradition of picking up toys for local families. Someday, we plan to continue this with our own little ones, letting them pick out toys for kids in our community that are less fortunate than them. We’re looking into Stockings With Care or Operation Santa – or both!

Jazz Standard Holiday Show:

I love live jazz any time of year, but it feels extra festive around the holidays. Jazz Standard in Gramercy is one of our favorites for big band style jazz and last year we went on January 1st which was such a fun way to kick off the new year.  

West Village Wander:

Is there any place prettier than the West Village around Christmas? I love taking a Saturday, hot chocolate in hand and just wandering through the streets and looking at everyone’s decorated doors. Grove Street is a particular favorite. 

Classic Movie at the Theater:

Our local movie theater plays classics like It’s A Wonderful Life this time of year and I want to make it a point to catch one – even better if it’s one I’ve never seen!


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As much as I love a good, colorful holiday moment (exhibit A and exhibit B) – I also love a simple, ‘winter white’ cold weather look.


I love how this ivory faux fur lined parka is neutral enough to go with everything but still really brightens up a dreary winter day (as opposed to my typical black parka that just plain depresses me by the time February rolls around). Perfect for taking a spin around the ice rink.

Speaking of ice skating – this Winter I’m determined to embrace the activities that can only be done in cold weather (instead of spending approximately 3 months wishing for 70 degrees to show up again). Even if that’s just cozying up inside and allowing more time to read, or finally watching a bunch of classic old movies I’ve never seen. Things I’d never do in summer. Winter is exactly the time! And if I do have to actually you know, leave the house, at least I’ll be bundled up in a cute coat.

Talbots Parka, Cashmere Sweater, Grey Ankle Jeans and Fair Isle Scarf c/o – all 40% off right now!  

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I always find the hardest holiday events to dress for are those that fall somewhere in between 0-NYE glitz. A Christmas Eve dinner with your in-laws for instance or your office holiday party. Where you want to be more conservative than say, a backless sequin dress, yet still dressed up and festive. This outfit is my solution.  


I love the simple shape of this knee-length wrap dress and the fact that it’s made fun by the metallic knit – which gives just the right amount of subtle sparkle. My office holiday party is always at the end of a regular workday so finding something that doesn’t look crazy when I walk to work at 8AM but still feels party-ready at 7PM can be tricky. This would definitely work. I paired with these cute embellished flats (my family functions are usually pretty casual so heels feel overdone) and these super lightweight statement earrings for a finishing touch. 

Also – this hairstyle looks fancy but couldn’t be easier to do. I’m going to add a quick tutorial to Instagram this week! Basically a tuck and roll situation.

Metallic Wrap Dress c/o Talbots |  Statement Earrings c/o Kendra Scott | Vintage Bag |Boden Embellished Flats – similar here or here

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The Steele Maiden: Holiday Style - Red Beret, Plaid Blazer and White Midi Skirt

This outfit feels a little bit like if I was a 2018 version of Audrey Hepburn who split her time between Paris and the West Village. Which is basically my dream.



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Throughout the guide, click on any product title text or product image to shop directly.

I’m so excited to share with you my 2nd annual ‘Complete Guide to the Holidays’ – featuring style tips for every occasion (from office holiday parties to Christmas morning), gift guides (there’s something for your tricky to buy for brother in law and your work wife), home decor ideas + my tips on best spots to visit in NYC this time of year. I’ll be adding new content to the guide each Monday for the next month so that you can continue to check back in and use this as your holiday handbook. Enjoy!



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Fashion, Travel & Lifestyle. Based in NYC.