Holiday Outfits for All Occasions + Holiday Gift Ideas

Holiday Outfit Ideas

Woohoooooo, the holiday season is upon us!  It’s time to eat tons of good food, see pretty lights everywhere, hang out with friends more often than usual, and catch amazing pieces during crazy sales!  YAS!  To kick it off and help us prepare for the holidays, today I’m partnering with J.Crew Factory to share three holiday outfit ideas for all occasions!  I’ve got holiday outfits for an office holiday party, casual events, and fancy holiday events.  Let’s get to them!

NOTE: J.Crew Factory is running a few sales today!  Get 40-60% off select items, or shop sweaters under $30!  Check if you can catch any of today’s items for 40-60% off!


Yellow Sweater + Statement Necklace + Green ankle pants + maroon pumps Yellow Sweater + Plaid button up + maroon bag + maroon pumps + green pants Maroon Pumps + Green ankle pants + maroon bag + Yellow sweater + plaid topGreen ankle pants + yellow sweater + plaid top + statement necklace + maroon pumpsbusiness casual look: yellow pullover + plaid top + statement necklace + green ankle pants

Office Holiday Party: Red Plaid Shirt + Sweater + Green  or Grey Pants
I get asked by a lot of you for ideas for what to wear to office holiday parties, and J.Crew Factory is one of the first places I’d look.  They always have the perfect items for a classy look for an office holiday party, like pants and skirts in holiday colors and tailored but playful shirts.

Here I did a layered look for work.  I used a red plaid top, which is one of my must-haves for fall and winter and is especially great for holiday looks.  You can style it casually with a quilted vest, dress it up with a skirt and fancy necklace, or wear it for a daytime office holiday party like I did here!

This one has a ton of fun colors that you can pull out and incorporate elsewhere in your outfit.  There are so many options!  Here, I echoed the yellow in the print and paired it with this chartreuse sweater.  BTW, this sweater comes in 15 reallyyyyy pretty colors for both cool and warm skin tones.  So good!  See them all HERE.

While you could do this outfit with jeans and tall boots for a casual look, for an office holiday party I went with pants in a sophisticated, gorgeous green!  I finished it off with maroon pumps and one of my go-to statement necklaces.  I love how colorful this outfit is while still being sophisticated for an office!

Shop for the Look:
sweater – wearing S  |  plaid top – wearing S  |  pants – size 6  |  necklace


Shop More Items for Office Holiday Parties:



Grey Vest + Buffalo Check Sweater + Skinnies + Riding Boots + Statement NecklaceHerringbone Vest + Grey Sweater Buffalo Check + Riding Boots + Brown Bag + Statement NecklaceVest + Grey Sweater + Skinnies + Suede Riding BootsStatement Necklace + Grey and Black Vest + Sweater + Skinnies + BootsSuede Boots + Layered Sweater + Herringbone Vest + Skinnies + Shoulder bag

Casual Holiday Outfit: Sweater w/ Holiday Details + Vest + Jeans + Boots
I don’t know about you, but most of my holiday events are very casual to dressy casual at best.  This is an outfit you can wear to cookie decorating parties, a potluck at a friend’s house, or a casual holiday dinner.

I NEED to tell you about this top!  First of all, it’s one of those that looks like two pieces but is really one, so you get that layered look without the fuss of layering. It is a thin sweater and loosely fitted.  Super easy to wear.  Secondly, the buffalo check is an adorable subtle nod to the holidays.  And most importantly, it is so, so versatile and can be dressed up or down effortlessly!

Above I styled it slightly dressier with one of my favorite necklaces again, but you could dress it down with a simple short pendant instead.  Dress it up further with black jeans + black pumps + moto jacket.  Or give it chic, edgy twist with faux leather pants + black pumps + a black blazer.  Or go casual chic with faux leather pants + black slip on sneakers.  Like I said, it’s SO versatile!

If you can’t tell, I love this top, haha!  It’s gonna be my go-to piece for holiday events this year!  Check it out in sizes XXS to 3X HERE.

Shop for the Look:
similar vest
–wearing XS |  sweater–wearing S  | 
 similar jeans  |  necklace


Shop More Items for a Casual Holiday Gathering:



Lace dress + Leopard Bag + Brown Pumps + Statement Necklace Leopard clutch + Red lace dress + Leather jacket Lace swing dress + Statement Necklace + Leopard Clutch + Brown pumps + Cognac Bag Lace swing dress + statement necklace + Leopard clutchCognac Jacket + Red Lace Dress + Leopard Bag + Statement Necklace

Dressy Holiday Events: Dress In a Holiday Color or Jewel Tones
A maroon lace dress has become my go-to for dressy fall and winter events. It’s classy, elegant, and timeless!  I’ve shown a similar dress to this several times over the last 5 YEARS–that’s how timeless this is.  To this day I still get asked where you can find a dress like that, and THIS IS IT!  Except this one’s even better–better made, a more vibrant color, and better fitting!

This dress is fully lined, minus the sleeves.  It’s a shift silhouette that is really, really flattering.  There’s a bit of curve built into it, then it floats away from your body.  After Katie and I took these pics, I told her, “This dress is COMFY!” It doesn’t hug or squeeze you anywhere.  Honestly it felt like I was wearing a nightgown, except much classier!

It comes in 3 colors: maroon, black, and navy which are all fantastic for fall weddings, fancy holiday parties, a dressy Christmas Eve church service, or nice holiday concerts.  Style this for warmer weather with black fleece lined tights + black booties + black faux leather jacket.

See all 3 colors HERE!

Shop for the Look:
dress – size 6  |  similar shoes


Shop More Items for Fancy Holiday Events:



In case you want to take advantage of sales, here are some gift ideas!  I especially love J.Crew Factory for men’s clothes and gifts!



Check out more gift ideas from J.Crew Factory’s gift guide HERE!


Created in partnership with J.Crew Factory



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