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Holiday Outfits for Every Occasion

Happy Monday, friends! I rounded up a bunch of holiday style in case you need ideas for events you have coming up.

Whether it’s a holiday cocktail party, at-home get together with friends, Christmas Eve church service, office party, or you just want to look cute for Christmas shopping… I’ve gotcha covered!

SIZING NOTES: I’m 5’5″ with an hourglass shape, and I usually take a 6/28 in pants/jeans, a small in tops, and size 8 shoe. I linked the sizes I’m wearing beneath the pictures. And by way of disclosure, gifted items are indicated by c/o. That means a company sent it to me; everything else I purchased myself.

Holiday Outfits for Every Occasion

In this first look, I love the juxtaposition of the cozy sweater and faux leather pants. The metallic pumps and oversized beaded earrings give it a festive flair. I didn’t want to leave the neckline bare, so I wore two small necklaces in complementary black and gunmetal tones. This is an outfit I’d wear to a Christmas or New Year’s Eve party at someone’s home or out to dinner with friends.

sweater c/o (S) // pants c/o (M; more sizes) // pumps c/o (8; also at Nordstrom) // earrings // necklace // necklace

Here’s a monochromatic look with the same faux leather pants. This time I paired them with a glittery black top, and I wore black suede pumps.

blouse (S) // pants c/o (M; more sizes) // pumps (8) // earrings

The key to creating a great monochromatic outfit is to have a mix of textures, so I topped it off with a faux fur jacket.

faux fur jacket (S; option/option/option) // blouse (S) // pants c/o (M; more sizes) // pumps (8) // earrings

If the invitation says “cocktail” or “festive attire” or anything like that, this dress is PERFECTION. The fit is amazing, and it’s super flattering and comfortable to wear all night. Throw on a leather moto or faux fur jacket to top off the look. I’d wear this to after-hours office party or a NYE bash at a friend’s house.

dress c/o (S) // pumps c/o (8; also at Nordstrom) // earrings // similar bag

For a dress that isn’t quite as va-va-voom, this red cable knit sweater dress is nice for church and work related events. It also comes in a pale grey heather, and it’s 50% off + free shipping with code JOY. If you need it right away, LOFT offers curbside pickup at most retail locations.

dress (S) // tights (B) // boots (8.5; on sale at Zappos) // bag // earrings

This tie sleeve blouse with sleek black pants is another conservative option for work or church. This blouse comes in lots of pretty colors, and there’s also this tie sleeve sweater, if you prefer something a little cozier. I’m wearing the Claret Red, but the Lush Green and Rich Cabernet are also really pretty for the holidays. The ivory and black are good options too.

blouse (S) // pants (M) // pumps (8) // similar earrings // necklace // necklace // bag

Here’s that look topped off with my black wool reefer. If you wanted to make it more festive, you could go with a faux fur coat.

coat (S) // blouse (S) // pants (M) // pumps (8) // earrings // necklace // necklace // bag

If you’re more comfortable in jeans, I’m right there with ya! I really like this Red Claret with dark wash jeans.

blouse (S) // jeans (28) // pumps (8; also at Nordstrom) // earrings // necklace // similar clutch

If you don’t want to blend into a sea of red and black outfits at your next holiday party, try wearing a pretty evergreen instead. This sweater is the Night Meadow color. See more of this look in this post.

sweater (S) // pants (M; more sizes) // sandals (8) // necklace // necklace // bag

And a sparkly top with black jeans is always a safe bet at the holidays. This top is unfortunately selling out, but here’s another good option at a great price.

sweater (S; option) // jeans (29) // pumps (8) // earrings

This look is similar, but the sequin top and sleek black pants take it up another notch.

sequin top (S) // pants (M) // pumps (8)

When an event calls for casual festive attire, pairing a fun statement sweater with jeans and knee boots is a good option. These Kendra Scott earrings add texture and shine to the cozy look.

sweater (S; also at Zappos) // jeans (28) // boots (8.5; on sale at Zappos) // earrings // bag (30% off with code EXTRA30)

The back of this sweater and the metallic clutch make this look party-ready. I would also top it off with my vegan leather puffer or a faux fur jacket.

And speaking of that faux leather puffer, here’s an example a winter date night look I would wear to a casual holiday party in a pinch.

jacket (S) // sweater (S) // similar jeans (28) // booties (8; option) // earrings // similar clutch

This sweater isn’t a traditional holiday color, but I think a pretty mauve can look really festive at this time of year. It’s fun to wear something a little unexpected. The wide boatneck and fine gauge cashmere look elevated and a little extra special. (This is the Mink, by the way, and I also have this sweater in the Merlot, which is another great option for casual holiday looks.)

sweater (S) // similar jeans (28) // booties (8; option) // earrings // similar clutch

Unfortunately, my booties have sold out in the black, but these are similar and 30% off with code GREEN30.

Aquatalia booties (size 8M; similar option)

And here’s how that  jacket looks zipped up. I do sometimes zip it because I often wear it when it’s cold out.

A+F vegan leather mini puffer (S)

If you like a pop of red to give a nod to the holidays, never underestimate the power of a good red accessory like a scarf. And also a red manicure! This is an outfit I wore to church last year at Christmastime.

coat (4) // sweater (S; similar for less) // jeans (28) // similar boots // similar scarf // earrings

Underneath, it’s just a simple neutral outfit that I’d wear anytime during the winter, but the nails and scarf give a nod to the holiday without being too over-the-top.

sweater (S; similar for less) // jeans (28) // similar boots // similar scarf // earrings

And while we’re dredging up pictures from last year, I found this one. I wish this tee was still in stock because it’s so cute. I saved it and can’t wait to wear it. It’s warming up this week, so hopefully I’ll have the chance. This is the perfect outfit for running errands this time of year or going to your child’s holiday event at school.

jacket // similar tees // jeans // similar sneakers

This is a cozier version with the same tee. Any holiday-themed graphic tee will work with these looks. Pair it with your favorite jeans, and then top it off with a cozy cardigan or an edgy leather jacket for the perfect casual-chic holiday outfit!

similar cardigans // similar tees // jeans // boots

And finally, this look is from two years ago, but I’ve always loved it, and I really wanted to show something with an ivory top. I love wearing ivory at Christmastime, but for some reason, I haven’t styled one yet this year.

This metallic sweater is no longer available, but there are lots of current options available. I love these OTK boots, but my current Sam Edelman knee boots work as well. Also, how fun are these earrings? And they’re still available, yay!

metallic sweaters // jeans // similar boots (option) // earrings

I hope this gives you tons of holiday outfit inspiration. See even more of my holiday style HERE!

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photos: Alison Cornell

Join the Conversation

19 thoughts on “Holiday Outfits for Every Occasion

  1. I’ve all of these looks, wish I had a party to wear any of them to! Ours will be quite casual this year so sweater and jeans and probably boots will do. 

  2. You have so many cute outfits. I love the fake fur and long coats. You’d really make an entrance with those. Wish I had some festive occasions to attend. Enjoy the holidays with your family!

  3. Can you tell me how your p448 sneakers fit? Do you wear the same size as all athletic shoes? I got the Jack and the John and I’m just trying to decide if they might be too big.

  4. I realllyyy would like to try to pull off the faux leather leggings style (because they look like obviously a dressier pant and not like you’d be showing up at a holiday party in the SAME black stretch ones you clean the house wearing, lol!), but (I think) I’d still be a little self-conscious about the “flash” of them (especially: having a pear figure with my weight centered around the hips and thighs). Know what?, though: I’d wear the red sweater dress as a tunic (for camo!) over them and, wear the pumps instead of boots.

    All of your recommendations are lovely choices and, your family should appreciate the work you no doubt put into the spirit of the season!🎄☃️

  5. So cute. You look so pretty in all the outfits and will be ready for any occasion for sure. Sadly to say, we won’t be attending any holiday get-togethers this year. Still recuping from covid(been a long ordeal for sure) and just won’t be planning any. Our kids all go to the other side for REAL Christmas day this year, so just the 2 of us and then we do our family Christmas with them New Years Eve weekend at my daughters. Usually I have all the holidays, but she offered this year, since we’ve been sick and they just moved this weekend into another home, so they are anxious for us all to see it. I have to say, I’m relieved I don’t have the pressure to get ready for the holiday. We hope to get to go out to attend our Christmas Eve service. As hard as its been to be sick with covid since before Thanksgiving, its given time to slow down and focus on what Christmas is really all about. I’m so glad I shopped early and have been done since first part of Nov. Now to focus on wrapping. 🙂 I’ve enjoyed your blog even more while home stuck inside. Thanks for all you do to get us ready for each event/etc. Have a great trip tomorrow and prayers for safe travels to and from. Keep us updated how its going. You know we all care.

  6. Great looks–a question on the Vince black pants. The product description lists the inseam as 26 1/2 inches but they appear to be longer. Are they ankle length on you? Thank you.

  7. Thank you for inspiring to look our best as we celebrate the reason for the season. All the outfits are beautiful! The burgundy/ oxblood tops look gorgeous on you!

  8. My goodness, all the outfits look gorgeous! Wish I had somewhere to wear the fun “fur” jackets, I really love the outfit with your black wool reefer, adding touches of red really sets it off. I have a long red wool coat but rarely get to wear it but will plan to get this black one soon; the possibilities are endless. Thanks for such great posts, you really inspire me.

  9. You look beautiful in every single out! Your hair also looks gorgeous.
    Thank you for styling all these outfits, you’ve made me feel inspired today! I have a couple of Christmas events coming up, and now i have some new ideas.

  10. Merry Christmas!
    Thanks for all these ideas…don’t comment often,
    But hv learned so much from you. I wore the J crew t lace shared years ago with black jeans
    to party Friday night! Always add my big Kendra
    Ear rings and suede pumps..so much fun!

  11. Hello! I purchased the sparkle Evereve dress and am looking forward to wearing it! However even here in SoCal, it is looking chilly over the next couple weeks. Any ideas of how to layer it for indoors when it’s too cold for sleeveless?

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