There is nothing I love more than the second Halloween strikes midnight and holiday mode becomes activated. Is it premature? Yes. Do people angrily tell me not to skip Thanksgiving? Yes. Do I know that the research says that folks who celebrate the holidays earlier and for a longer period of time are happier? BIG yes. Do I have the data to back up this claim? No, but I definitely saw it on the interweb at some point or another.
The joy of the cozy holiday season gets me beyond excited for all the things.
Holiday traditions: This year, I said I’m over it and bought an Elf on the Shelf kit already made for me (SUE ME!). I think this is parental cheating, but I feel so happy. I also think we’re at the end of the road, so why not end the tradition in style?
And if you’re also feeling (or even anticipating) a little holiday burnout, Tricia Torley has a great post here on surviving the holidays as an exhausted Mom. Clearly, we’re not alone.
I am also really excited to try this new tradition that I saw on Shark Tank, because no one loves an activity that goes with a book more than me.
I love holiday decor: The garland, the trees, the red, the green, the gold, the smells of a great balsam-scented candle—all trigger the dopamine receptors in my brain to start an absolute rager.
Lastly, I love holiday dressing! So much so that I often prepare way more outfits to wear than I end up needing. I also end up buying a few awesome pieces to wear as I celebrate the season. But as I enter my age of intention, I’m trying to be mindful of buying these holiday outfit items with the understanding that they must be able to live on beyond the holiday season.
That was the goal with this post: identify a few holiday pieces I love and challenge myself to style them in ways that will carry through the colder months. No one-hit wonders (only “I Want a Hippopotamus for Christmas” by Gayla Peevy can truly take the crown of a holiday one-hit wonder, not my furry sweaters).
Without further ado, here are some festive AF outfits for you to browse! You’ll notice I found a holiday-themed piece and styled it several ways to ensure the item proves its versatility. I also tried to use things that I own and can vouch for (noted in the captions). Happy scrolling!
P.S. - You know the drill, some affiliate links are included below.
LOOK 1 - HOSTESS WITH THE MOSTEST
I have literally never bought anything from this store, but the second I saw this set, I was completely sold. The pants arrived yesterday and they are AMAZING. It looks like the perfect Christmas Eve hostess outfit — something I can wear while running around putting frozen appetizers in the oven, cleaning up wrapping paper, and yelling at my kids to remember to say thank you.
For all things makeup and lipstick, PLEASE head over to Lovey’s substack.
LOOK 2 - OFFICE READY
The pants look great with the set, but they also need to be versatile enough to wear on their own. Paired with a simple cardigan and flats, they’d be perfect for work!
Last week, I wore a royal purple sweater with khakis, and one of my students told me I looked like a young Justin Bieber (see pic here). I can’t wait to see what they think of these pants.
LOOK 3 - DATE NIGHT
Every year, when my mom asks what we want for Christmas, we ask for a gift card to our favorite restaurant and a night of babysitting. This would be the perfect freedom fit.
LOOK 4 - HOLIDAY PARTY READY
A cute little remix of the top to wear to any holiday party! I just want to put it out there: I am ALWAYS ready to dress to impress for a holiday party, but somehow, every year, we never have any to go to (lol).
In all fairness, I love that our teacher squad sometimes goes out for wings in the most casual way ever, so you won’t hear any complaints from me in that department.
LOOK 5 - FESTIVE & OFFICE READY
This is as close as I’ll get to teaching in pajamas while still looking chic! The fringe at the bottom of these pants is gorgeous, and the fun print makes them a true party pant. I bought these as a just-in-case option in case the first feather pair didn’t work out, but in a truly serendipitous moment, I realized they were both just meant to be! <insert evil laugh>
LOOK 6 - A LITTLE FANCY FOR A TUESDAY
Another great outfit if you’re looking for something festive for work or an easy transition from desk to cocktail hour! It would also be perfect for hosting any of the upcoming holidays. I think “party pants” are critical for all the moving around you do as a host, not to mention starfishing on the couch once the last guest has finally departed.
LOOK 7 - HOME FOR THE HOLIDAYS
This is the ultimate “What are we wearing to the living room?” outfit, if you ask me. The only thing better would be a full groutfit set with a hoodie and sweatpants. We usually spend New Year’s Eve at home, and I can definitely see this being a contender.
LOOK 8 - THANKSGIVING & HOLIDAY DOUBLE PLAY
I actually love this outfit for Thanksgiving… and Christmas… and possibly every other holiday after that. Probs not the Fourth of July. A cute blazer with a wrap belt and your most comfortable, stretchy jeans (possibly a size up for the post-turkey expansion). Also, this lip balm (gifted) literally tastes like a cookie, which seems important to mention.
LOOK 9 - A NIGHT OUT, BUT MAKE IT COMFY
Similar to the look before this, but swap in satin pants with an elastic waistband and furry loafer slippers. The easiest hack for dressing up any outfit for the holidays, you ask? A unique, fun earring.
This would be perfect for a holiday theater outing. We’re going to see Michael Jackson: The Musical, and I cannot wait. Last weekend, we saw Aladdin on Broadway, which reminded me why I have a bit of a love-hate relationship with high-waisted jeans. The second those lights went down, that top button freed herself in the best way possible.
LOOK 10 - BRUNCH WITH FRIENDS
Being able to transition this blazer into a more casual outfit was critical in deciding whether it was for me.
Unrelated, but related: I don’t think I’ve ever actually gone out to brunch. But should the spirit ever call me, I would absolutely wear something like this and order a giant plate of brioche French toast.
LOOK 11 - WESTERN MEETS HOLIDAY
I love any excuse to wear my western boots. For the record, these babies turn one year old on Black Friday! If you’ve been in the market for a quality, lifelong pair of western boots, Tecovas will be running their sale in the next few weeks.
I will forever thank OFELIA for influencing me in the best possible way to buy my most favorite pair of shoes ever.
LOOK 12 - HOLIDAY WITH AN EDGE
Same blazer, but this time paired with a sheer turtleneck and leather pants to give the look a little edge.
LOOK 13 - FUR & LEOPARD, OH MY!
Faux fur is truly having a moment, yet again. I own this furry cardigan and can say with confidence that I am obsessed. The leopard clutch is on my wish list, so fingers crossed.
LOOK 14 - WE LOVE WINTER WHITE
I love the way navy looks paired with off-white denim. The fun pops of burgundy add just the right amount of life to this outfit. Pull your hair back into a ponytail or a half-up, half-down style with a velvet bow and it’s chef’s kiss!
LOOK 15 - A VERY MERRY MONOCHROME
Monochromatic magic, if you ask me. You know I love any excuse to wear my Cosmo pants. Add a silver heel and a fun bag, and you’re good to go!
And there you have it! ‘Tis the season for festive dressing. I think the key is simple: find pieces that you love, then play around with Canva to see how versatile they really are. Can you wear them to work, after-hours, holiday celebrations, and casual outings? If so, they might just be worth the investment!
Let me know if you have a favorite look or favorite piece that wears well beyond the holiday!
Good luck out there, friends. Thanks for always stopping by and hanging out with me here. I appreciate you more than you know.
Love ya, mean it!
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Items marked with an asterisk (*) were gifted. I only share products I’ve personally tested and genuinely love!
Ok these are excellent and I want them all!!!!
These outfits are not only gorgeous but so unique and unlike a lot of what I’ve been seeing repeatedly. I am truly a fan of Boden (I have dresses from them that still look brand new that I purchased a decade ago) and that top/bottom set is magical! Also I endorse you buying the elf on a shelf kit. I actually feel relief for you.