What to Wear to Dressy Casual Holiday Events

6 Outfits to Wear to a Dressy Casual Holiday Party

What to Wear to a Holiday Party

For today’s portion of the Holiday Style Series we’re talking outfits you can wear to dressy casual holiday parties or events.  These can work for a ton of different events–basically anything that’s not super casual and anything that’s not super fancy–like an adults-only Christmas gathering, a holiday lunch or dinner for work, holiday concerts and kid’s performances, a Christmas party at church, or even to a Christmas Eve service if your church is fairly casual like mine is!

SIZING INFO: I’m 5’6″ and usually wear size S/M or 6/8 in clothes and 8.5 to 9 in shoes.

Black Moto Jacket + Maroon Swing Dress + Leopard Clutch + Black Booties Black Moto Jacket + Maroon Swing Dress + Leopard Clutch + Black Booties Leopard Clutch + Black Moto Jacket + Black Booties + Maroon Swing Dress Maroon Swing Dress + Black Moto Jacket + Black Booties + Leopard Clutch

Dress + Statement Necklace + Faux Leather Jacket
This is a way to wear those Old Navy “pajama dresses” (as I like to call them) in colder weather.  Dress up any solid dress with a statement necklace and a faux leather jacket.  Both of those pieces add a “harder” element to a soft and shapeless dress to add structure and polish it up.

To add warmth to a dress: I usually wear fleece lined tights (Old Navy has some HERE) which aren’t quite as warm as leggings or pants but are definitely warmer than regular tights.  I also layer a thin HEATTECH from Uniqlo, which I’ve talked about before.  They have shorter arms so they stay hidden under shirts.  I also prefer the scoop necks over crewnecks for that reason.  I wear THESE in size M.  They’ve also come out with an “extra warm” version HERE that I haven’t tried yet.

My particular dress is super soft and stretchy, which is why I call them pajama dresses.  You could sleep in them, they’re so comfy!  But note they are a bit shapeless so they don’t work well for body types that require more structure.  I own this dress in 3 colors in the long sleeve version and other colors in a tank version.  This one is the long sleeve dress which I got last year and it’s back again in several colors HERE!  They tend to run shorter than I want, so sometimes I order Tall and regular sizing to check length, and Old Navy has inconsistent sizing so sometimes regular work, sometimes tall works, and sometimes tall is the same length as regular!  There’s also a similar longer 38″ version on Amazon HERE in a variety of colors, plus it has pockets.  I tried them and they are thinner than the Old Navy version.  While size small in the Amazon dress was fine, I preferred a medium.  I didn’t find them as flattering on me as the Old Navy dress, mostly because the pockets competed with my hips.  However if you don’t have that problem, check out the Amazon version!

Shop for the Look:
Dress: Old Navy (exact–wearing M, similar)
Jacket: c/o Shein (similar
Fleece-lined Tights: Bare Necessities (similar)
Shoes: Nordstrom (exact–wearing 8.5)
Bag: Nordstrom (exact)

 

Holiday Office Outfit: Green Navy Plaid Top + Black Pants + Black Pumps + Black Clutch + Gold Pendant Holiday Office Outfit: green navy plaid + black pants + gold pendant + clutch Holiday Office Outfit: green navy plaid + black pants + clutch + gold pendantHoliday Office Outfit: green navy plaid + black pants + black pumps + gold pendant + black clutch

Printed Blouse + Black Jeans or Slacks + Pumps
Next is an outfit I’ve shown before but totally works for dressy casual everything.  This is a super simple outfit formula that works with any printed blouse.  Just wear darker jeans or black jeans to dress it up a bit more, and be sure to add pumps!

Shop for the Look:
Top: J.Crew Factory (exact–wearing M)
Jeans: Nordstrom (exact–wearing size 6)
Shoes: H&M (similar)

Necklace: c/o Dear Mushka (exact)
Watch: c/o Daniel Wellington (exact)
Clutch: c/o Sole Society (similar)

Here’s another printed top + black jeans outfit that uses colored pumps instead.  I wore this to sing for our church’s Christmas Eve service last year!

Navy Floral Print Top + Black Jeans + Maroon Pumps + Black Faux Leather Jacket Navy Floral Print Top + Black Jeans + Maroon Pumps + Black Leather Jacket

Shop for the Look:
Top: ModCloth
Jacket: c/o Shein (similar
Jeans: Nordstrom (similar–I wear size 6)

Shoes: c/o Naturalizer (exact–I wear size 9)

Watch: c/o Daniel Wellington (exact)
Skinnies + Graphic Tee + Tan Blazer + Black Pumps Tan Blazer + Graphic Tee + Skinnies + Black Pumps + Clutchblazer + dark wash jeans + heels + graphic tee
Graphic Tee + Blazer + Jeans + Pumps
A blazer with pumps can dress up nearly any graphic tee or graphic sweater!  Use a graphic tee with a holiday theme, and try adding at least a bit of sparkle.  My earrings are champagne shimmer and my clutch is glittery.  The touches of sparkle help dress up the look just enough for a dressy casual holiday party.  I’m still super in love with this outfit and I can’t wait for the holiday parties to start so I can wear it!
I’m so glad a ton of you scored the penguin tee and blazer during the huge sales, but in cased you missed them they are both still hugely discounted!  (Shop them below.)
Shop for the Look:
Top: J.Crew Factory (exact–wearing S)
Blazer: J.Crew Factory (exact–wearing size 4)
Jeans: Nordstrom (exact–wearing size 4)
Shoes: H&M (
similar)
Bag: Amazon (similar, similar)
Earring: c/o Nickel & Suede (exact–wearing size M)

 

Black Moto Jacket + Lace Top + Black Pumps + Statement Necklace + Clutch Black Moto Jacket + Clutch + Black Jeans + Black Pumps + Statement Necklace Maroon Lace Blouse + Black Skinnies + Black Clutch + Pumps Lace Blouse + Black Moto Jacket + Skinnies + Black Pumps + Statement Necklace

Solid Top w/ Detail + Dark Jeans + Statement Necklace + Faux Leather Jacket
This is a variation of Outfit #2, but if you’re going to use a solid top as opposed to a printed one, try finding one with interesting details to take it up a few notches.  Go for something with lace, ruffles, a bowtie, pleats, etc.  My top is sold out, but two maroon alternatives with interesting details are this really cute high neck top with subtle textured hearts all over it HERE and one with a geo print neckline HERE.  Then add a statement necklace to add some shine and a focal point!

Shop for the Look:
Top: LOFT (exact–wearing M, similar, similar)
Jacket: c/o Shein (similar
Jeans: Nordstrom (exact–wearing size 6)
Shoes: H&M (similar)
Bag: c/o Sole Society (similar)
Necklace: c/o J.Crew Factory (exact)

 

Red Plaid Button Up + Black Sweater + Leopard Print Red Plaid Button Up + Black Sweater + Leopard Print + Black Jeans Red Plaid Button Up + Black Sweater + Leopard Print AccessoriesRed Plaid Button Up + Black Sweater + Leopard Print

Plaid Button Up + Pullover Sweater + Leopard Print Accessories
Lastly is an outfit I wore to a holiday Christmas party last year.  I’m not huge on pattern mixing, but I do love plaid with leopard print!  This is an easy way to dress up a red plaid button up.

Shop for the Look:
Top: J.Crew Factory (similar, similar)
Sweater: Nordstrom (super similarsimilar)
Jeans: Nordstrom (similar–I wear size 6)
Shoes: Sole Society (similar, similar)
Clutch: c/o Gray Monroe (exact)
Watch: c/o Daniel Wellington (exact)

Got any events you could wear these outfits to?  If you need something fancier or something more casual, check out the rest of the Holiday Style Series!  Coming soon are looks for Outdoor Activities With Kids and Cozy Casual Gatherings With Friends!

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