Dressing for the Holidays


I love an ‘Aprés Ski’ style sweater this time of year – from something that literally spells it out to more classic fair isle or fun novelty knits like the snowflake one I’m wearing here. They feel like December to me. Here – a few of my favorites that would make a great gift or just something cozy for yourself now that it’s cold.


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If we’re being honest – I’m still coming to terms with the fact that this holiday season will have more occasion for leggings and far less for sequins. So in an effort to balance being comfortable and cozy at home but also still feeling a bit festive, I came up with 10 outfit ideas that will be perfect for the season ahead. Lots of relaxed denim, cozy sweaters and simple styling. Hopefully this inspires you to find a new piece or two that will make the holidays feel special or wear something you already own in a new way. The full IGTV video is here and all outfit details are below.

I’m not a leggings person at all but this pair is a 10/10. Super high waisted, totally opaque and they don’t stretch out throughout the day. Pair with sequins and slippers or a cute ski sweater and comfy boots.

LOOK 1 (Above Left):

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This headband and velvet hair bow get a lot of wear whether I’m staying home or out and about. Pair with extra plaid or a chic, metallic vest.

LOOK 3 (Above Left):

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This black crewneck is a great base layer. Pair with a mini skirt and tights or with lace trousers and a leopard scarf.

LOOK 5 (Above Left):

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A pop of plaid always works – whether tossed on over a velvet tank or as a finishing touch with a bright sweater dress.

LOOK 7 (Above Left):

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Navy and red is a favorite combo this time of year – and again, clearly, plaid. A cotton turtleneck paired with a plaid button down or a classic pajama set with a cute headband.

LOOK 9 (Above Left):

LOOK 10 (Above Right):

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From the general consensus that I’ve gathered on the internet – a lot of us are struggling right now. We’re tired from the election/news cycle, we’re missing our family and friends, we feel daunted by the thought of renewed Covid-19 restrictions (my dear friend in Minnesota just went into full lockdown again in their town), we’re sad that the holidays won’t look like normal this year. I get it. And I feel all of it too.

My family just made the tough decision not to gather for Thanksgiving this year – a first for us all aside from the year that Adam and I were in LA. My brother in law traveled recently so he needs to quarantine, my niece and nephew are still in daycare, Adam still works in the office – so even to have just my immediate family together (3 different households) would put my parents at risk who are in regular contact out of necessity with my two grandparents, both in their 90s. A meal together just didn’t feel worth the risk.

Which means Adam and I will celebrate here in the city for the first time. Since I wasn’t about to attempt to cook a full turkey dinner in our small kitchen, we ordered a multi-course meal from a favorite local restaurant (Friend of A Farmer) to-go. It feels like a great way to support a local business and also get something that still feels special. In a situation that felt like sort of a bummer, I’m now really looking forward to a small, quiet holiday – just the two of us.

It’s that approach of focusing on simple joys that I’m trying to take to heart for the whole rest of this uncertain season. I’m talking Little Women-era basics at this point. The things that you’re otherwise always too busy to slow down and really revel in. Things that feel cozy and content. Here are a few of the simple joys I plan on indulging in this season.

  • Pick up a holiday scented candle (this one is a favorite) and string some lights. Now that it gets dark early I find the warm glow so comforting in the evening.
  • Treat yourself to a new flavor of tea or coffee to make at home. I’ve been loving a cup of peppermint tea in the evenings while I read.
  • Take a long, hot bath – extra bubbles too.
  • Handwrite letters (or holiday cards!) to friends and family that you might not get to see in person this season. Mail like that really makes people’s day.
  • Bake something – even if it’s out of a box. We just got a gingerbread mix from Trader Joe’s I’m excited to try. I love when the whole apartment smells like something fresh out of the oven.
  • Devour a new show – I mentioned on IG stories but The Queen’s Gambit on Netflix is incredible and I’m planning to dive into the latest season of The Crown today (Princess Diana here I come!) – or have a holiday movie marathon. Love Actually is always my favorite.
  • Play an old-fashioned board game. We bought Scrabble last year and it’s one of our favorite at-home date nights. We usually mix up a cocktail and put on our favorite records too. Finding an online game to play with a friend could be great too though!
  • Speaking of cocktails – is there anything a homemade hot toddy can’t solve? If whiskey’s not your thing – substitute a hot chocolate with extra marshmallows.
  • Pick up a new book and get lost in it for an afternoon. I’m currently reading Royal Holiday which is super sweet. And I plan on sharing a whole round-up of other cute holiday-themed books soon!

Sometimes simple joys are the best kind.


(Wrap + Corduroys c/o Talbots, Ballet Flats c/o Margaux NY – enjoy 10% off your order with code: STEELE10)



Houndstooth, buffalo check, tartan.. no matter how you print it, I’ve always loved a holiday plaid. From a small dose, like my favorite knotted plaid headband, to a more statement making houndstooth wrap – from now through New Year’s I’ll be finding lots of ways to wear these festive prints. Below – my top picks on the market this year.


  1. This set of 4 plaid mugs would make a cute gift for someone along with a selection of their favorite teas or hot chocolate.
  2. I’ve had this bag for a couple of years and love that it adds a pop of pattern to a basic black winter coat.
  3. A pretty plaid tassel keychain that can also charge your phone? Genius.
  4. I love this plaid print that J.Crew does and this year the button down comes in a cozy flannel.
  5. Will I ever tire of personalized mugs? No. The answer is no.
  6. If ever there was a sign of the times in 2020 it’s holiday face masks. I love the colors in this 3 pack and figure if I’m going to be wearing them constantly (which I most certainly am) they might as well be cute and match my sweaters.
  7. For the plaid enthusiast in your life! I’m swooning over this coffee table book dedicated to tartan.
  8. These sherpa lined blankets would be the perfect thing to curl up with as you watch holiday movies this year.
  9. I just got this kilt-inspired mini skirt and am in love with it. I wore it with boots here but will be pairing it with black tights as it gets colder.
  10. This houndstooth Christmas tree ornament feels very ‘ski chalet’ to me.
  11. I tend to think a lot of holiday doormats are too over the top but this subtle plaid one is SO chic.
  12. I have these plaid kitten heels from last year (the plaid was more multi colored) and they sold out so fast. I actually love the black watch plaid they come in this year even more – don’t wait on these!
  13. My favorite headband that I can miraculously wear all day without getting a headache. So cute with a simple sweater.
  14. Do I need these pink and red plaid block heels? No. Do I want them? Absolutely.
  15. I just got this houndstooth wrap and it’s like wearing a veryyy stylish blanket all day. I love it.
  16. No plaid round-up would be complete without a classic pair of holiday pajamas. I want to put these on and wear them straight through the new year.
  17. I love the shape of this satchel and, despite being a somewhat bold pattern, can think of a hundred ways I’d wear this.
  18. I gave up on bulky wallets years ago and instead just use these sort of minimal change purses. This one would make a great present for someone with a gift card tucked inside.
  19. When in doubt, put a plaid bow on it. This one is for your hair but could also top a gift box!
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LET’S CATCH UP 12.20.19

I honestly can’t believe that as you read this I’ll be at the office for the last day in 2019. How? Also, how will I get it all done before a (hopefully) blissful 12 days off work?? Alas… a few things on my mind before we head out into the weekend and the holiday weeks ahead. Have a good one friends!

  1. I’ve loved watching blogger Meghan of Wit & Whimsy’s campaign to spread kindness this season – from encouraging others to make donations to their favorite charities to simply being a big nicer to our cashiers and delivery people this season, the world needs more of this. And it shouldn’t end at the holiday season.
  2. In New York it feels like winter arrived about a month ago, but technically tomorrow is the first day. I plan on baking cookies and cozying up in the sweater and scarf combo I’m wearing here.
  3. I can’t wait to catch up on a few new books over my holiday break. If you’re looking for a great book to dive into, I recapped the 10 best books I read in 2019 here.
  4. I’ve still got a few things on my holiday bucket list that I want to get checked off this weekend – including making it uptown to see the Rockefeller tree and Fifth Avenue windows. But we’ve already been ice skating, wandered through the West Village and bought tickets to see a classic Christmas movie in the theaters. Okay, so maybe Edward Scissorhands isn’t what everyone would consider a classic, but it’s a favorite of mine and I can’t wait to see it on the big screen. Even better – the Nitehawk Theater is Brooklyn serves brunch while you watch!
  5. Speaking of winter’s arrival – I’m ready to book a warm weather vacation for the new year asap. We’re considering St. Petersburg in Florida, returning to Miami or heading to Mexico. Send recs!


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