Fall/Winter Fashion
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Holiday Outfit Roundup

Happy Monday, friends! I’ve rounded up some holiday style inspiration in case you need ideas for events you have coming up. Some of these looks are new, and others I’ve shared recently or in years past, but hopefully there’s a little something in here for everyone.

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.

Holiday Outfit Roundup

This first outfit features a bold red velvet halter top with contrasting pink ribbon at the neck. This top is spendy, but it’s one of those special pieces you can keep in your closet for years and pull it out for those occasions when you really want the wow factor.

velvet halter (S; black option) // coated bootcut jeans (29; option/option) // pointed toe bootie (8) // crystal drop earrings // clutch

You can wear this top tucked or untucked; I photographed it both ways. Also, you can adjust the neckline to sit as high or low as you want. I probably have it pulled up a little too high here, and I lost the pretty keyhole feature. When I go to wear it, I’ll make sure to adjust it so that doesn’t happen.

Look how fun it is from the back! I just think this top is so cute. It could be a little chilly, so I’ll top it off with a faux fur jacket or faux leather puffer.

Paired with black coated bootcut jeans, this is a great look for a holiday dinner out or festive-casual home party, and the crystal drop earrings and crystal frame clutch are the perfect completer pieces to this casual-glam holiday look.

For a monochromatic look, I love these velvet ankle flares with this sequin tee from Anthropologie. The flares are the Paige Claudine, the same style as the off-black jeans I wear so much. I love how the ankle-length style shows off my booties.

sequin tee (S; option) // velvet flares (28) // booties (8) // similar jacket // earrings // clutch (option)

And this top is another fun one! These sequins are large and in charge, and they actually make a rustling sound as you move around. So fun!

It was on sale last week, and most sizes have sold out in the black, but it also comes in a really pretty rose color as well as one they call champagne. It runs true to size, with a generously boxy fit.

This Sanctuary sequin tee is another option, if you prefer something more understated and form fitting. It runs slightly small, and it’s on sale.

sequin tee (S) // Paige Claudine in Slater (28) // booties (8) // old earrings and bracelet

I wore the same pointy toe stretch booties with the stiletto heel with both of these looks, and this is the faux fur jacket I mentioned above. I really wish it was still available in black, but here’s another option.

Here’s a similar look with a silver sequin tee. I love the v-neck on this one, and it’s the perfect length. I shared this as a potential NYE outfit, but it would work for so many types of events this month.

sequin shell (S; option/option) // coated bootcut jeans (29; option/option) // pointed toe bootie // necklace // necklace // earrings

I topped this one off with my faux leather puffer. You can get more details on this look in this post: What To Wear for New Year’s Eve.

sequin shell (option/option) // faux leather puffer (option) // coated bootcut jeans (29; option/option) // pointed toe bootie // necklace // necklace // earrings

Here’s a look that’s a little more conservative. I love the non-traditional color palette, and those who prefer to have some arm coverage will appreciate this blouse.

The painterly metallic detailing and sheer puff sleeves are such pretty details, and the bodice is lined, so there’s no show-through to worry about.

blouse (S) // pants (6) // pumps (8) // clutch // earrings // similar necklace

And this is another monochromatic all-black look, this time with a long sleeve sequin tee and black trousers. I particularly like this one for New Year’s Eve.

You can see more of both of these looks in this post: Beyond Red & Black: Festive Holiday Attire.

sequin top (S) // pants (6) // booties (8) // earrings

Here’s more of a cozy New Year’s Eve look, with a whimsical sweater you can pair with your favorite black jeans.

I styled it two ways, first with raw hem ankle flares in a cool faded black wash. This one I wore with suede booties, for those who tend to get cold.

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

And here’s an option with washed black straight ankle jeans and pumps. I would definitely glam up these looks a bit with fun earrings.

sweater (S) // similar jeans (option/option) // pumps (8) // earrings

When you need something for a church event or Christmas Eve service, this green sweater dress is perfect. Green is every bit as festive as red for the holidays, but not quite as predictable.

Don’t get me wrong; I love a red dress. But holiday parties often look like a sea of red, and it’s nice to stand out… in a good way, of course!

sweater dress (S) // tights (B) // pumps (8) // similar earrings // clutch

This dress has a hint of metallic thread that gives it a festive glimmer, and I wore crystal earrings to coordinate but hopefully not compete with the jeweled buttons on the shoulder.


I wore black tights and black suede pumps, but boots would work too. This dress runs a little big; you may want to size down if in between. It also comes in black, if you like the dress but prefer a more subdued color.

Another option is this black and white fair isle sweater dress. This one is nice because you can continue to wear it all winter long; I’m not sure I’d wear the green after the holidays.

sweater dress (S) // tights (B) // boots c/o (8) // earrings

This time I wore knee boots to balance out the bulkiness of the sweater. Both are 40% off right now with code COZY, and both come in petite sizes.

Here’s an outfit from last year with a pretty tie sleeve blouse and sleek black pants that’s another conservative option for work or church. This blouse comes in lots of pretty colors; I’m wearing the Claret Red, but the Alpine Green is also really pretty for the holidays.

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

And don’t overlook a bold fuscia for holiday looks. I paired this cashmere v-neck sweater in a gorgeous magenta with those black coated bootcut jeans, this time with pumps for a more traditional look.

sweater in Plumier (S) // coated bootcut jeans (29; option/option) // pumps (8) // earrings // similar necklace

Or you can also wear it with those washed black raw hem ankle flares and booties for a more laid-back vibe.

sweater in Plumier (S) // black flares (28; option) // boots (8) // earrings // similar necklace

Finally, if you just want to look cute and festive as you go about your daily errands or perhaps do some Christmas shopping, how fun is this fair isle scarf with a red thermal and white puffer fest?

similar puffer vest (S) // waffle henley (S) // jeans (29) // fair isle scarf

These classic straight leg jeans are only $30, by the way. They do stretch a bit, so buy them snug, and you’ll probably want to size down. They also come in short, long, and extra long lengths!

I also love this geo print mock neck sweater with the crisp white denim.

sweater (S) // jeans (29; option) // boots in Cloud Suede (8) // earrings

This sweater is soft and cozy, and it’s on sale for $39 with code COZY.

Another option is this red fair isle sweater with blue jeans. It also looks great with white denim, but I also find it really pleasing with these medium wash raw hem flares.

sweater (S) // flares (28)// boots (8) // earrings // sunnies

I hope this gives you tons of holiday outfit inspiration! The only category I’m really missing here is a cocktail dress for semi-formal events, but Nordstrom has a pretty good selection right now, if you’re in need of something.

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photos: Alison Cornell

Join the Conversation

21 thoughts on “Holiday Outfit Roundup

  1. Love all your reccomendations and follow your blog regularly b/c options are actually very wearable! But I was wondering if you could share your homes interior pain color featured in most of today’s post. Thank you

  2. Sooooo many good ideas…I’d scroll down and then scroll back up. I love the velvet halter with the black flares. XO

  3. I have the coated Joe’s Jeans and have worn them to 2 Christmas parties (I hadn’t been to a holiday party in 3 Christmases!). The first one was with a silver and black top, and yesterday I wore them to a party with an all-black dress code; I wore a solid black crew neck pullover sweater. It was so fun seeing most people in all black– it was so elegant. TBH, the 2 people who didn’t wear black really stuck out.

    I love those jeans!

  4. What do you wear under the sweater dress so it doesn’t cling. I think you have made a recommendation in the past. Thank you.

      1. I love a full slip under any dress, makes such a difference. I actually have a couple that were my mother’s, such nice flowy material, very old but still work.

  5. As pretty as all of the sequin and dressy tops are, the white vest, holiday scarf, & red tee look is my favorite. That’s because our lifestyle is very casual.

  6. Wow!
    So many beautiful options
    I love all the black sparkle tops so elegant!
    I Hv a black lace you recommended years ago, I still wear!
    Thank you great ideas!

  7. Would you consider doing a post on updating our black dress pants at all price points? We all need a pair of dress pants and in the winter it’s typically too cold to wear a dress here. Mine are looking a little dated!

  8. I like the red halter top and black coated jeans outfit on you. I clicked over to get the details on the halter top and saw your picture on the Evereve website!

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