Dressing for the Holidays


Is there anything more fun than holiday shoes? Sparkles, satin, plaid, bows – gangs all here. While these are obviously begging to be taken out to a holiday party, I argue that you’ll get lots more bang for your buck (and feel infinitely more festive) if you wear a pair all throughout the season. Try sparkly mary-janes with jeans and a cozy knit. Or a fancy pair of booties with a simple sweater dress. And when you’re ready to go all out on New Year’s Eve – you’ll have already broken in your dancing shoes.


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Earlier this Fall I posted a Fall Capsule Wardrobe IGTV and corresponding post here and the response was so positive that I knew I wanted to do it again for the holiday season. I’ve been making a concentrated effort all this year to really only add pieces to my wardrobe that I love and that can be worn a variety of ways. Dressed up for a dinner date, pulled together for a day at the office or dressed down for weekend’s running around the city. These holiday pieces from Talbots can do all of that. They’re fun and festive but I know I’ll be wearing these long past Christmas and straight through the winter. Below, each look + links to shop.

Hope that this inspires you to pick up a few new holiday pieces to spruce up your own wardrobe and try a new way to style some of the things you already own and love. Don’t miss the full video here.






*A special thank you to Talbots for sponsoring this post. As always, all opinions are my own.

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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 © 2012

Fashion, Travel & Lifestyle. Based in NYC.