What to Wear to Dressy Casual Holiday Events

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.

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)

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!