Dressy Holiday Outfits for Colder Weather

Dressy Holiday Outfits For Colder Weather

Huge thanks to Macy’s and ShopStyle for sponsoring this post

Anyone get STUMPED on how to dress up when it’s chilly outside?  Dresses with bare legs and open-toe shoes look fantastic, but in case that’s not practical for your climate, today’s post is for you!  When thinking about dressy holiday outfits for colder weather, I always rely on a few go-to tricks to pull together a fancy holiday look without freezing my buns off.  Today I’m partnering with Macy’s and ShopStyle to share my tricks and show you some dressy holiday outfits!

Growing up, Macy’s was my go-to store for dressy attire, so I knew it’d be the perfect place from which to showcase dressy holiday looks.  Macy’s has tons and tons of dresses, dressier pants, blazers, and tops at super affordable prices, and I can’t wait to share some of them with you today!

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


red and black floral dress + black tights + black flatsblack tights + red and black floral dress + black flats  black flats + red and black floral dress + black tights black tights + red and black floral dress + black flats

Dress + Fleece Lined Tights + (Jacket)
I know most people loathe dresses in colder weather, but sometimes, especially for dressy holiday events, you’ve gotta wear one.  One thing I always recommend to stay warmer while wearing a dress is fleece-lined tights.  Yes–tights LINED WITH FLEECE! 🙌🏽 These are a game-changer for dresses!  Check out the ones I’m wearing HERE.  I wear size S/M.

I assume you’ll wear a coat while commuting to your event, but in case you need to stay warmer indoors, I also recommend wearing a thin layer on top underneath your dress.  One extra layer can go a long way!  Also, add a cropped moto jacket, blazer, or cardigan on top!

To make dresses work in colder weather, I always look for one that I can wear with black tights since most fleece-lined tights are black.  This is fairly easy around the holidays because popular holiday colors like red, dark green, maroon, and jewel tones look fantastic with black.

The dress I’m wearing above is SO GOOD.  It’s got a really flattering fit and flare silhouette.  The ruching at the waist makes it even more flattering.  The print is perfect for dressy holiday events, like a Christmas concert, ballet performance, or Christmas Eve service at church.  The top half is stretchy and comfortable to move around in.  And it has POCKETS.  Done deal, friends!  See it HERE.  I wear size 6.

I topped off the outfit with a pretty red clutch.  PERFECT for holiday looks!  It’s available In red and black HERE and currently 40% off!

Shop the Outfit:
Dress: c/o Mac’s (exact–wearing size 6)
Tights: c/o Macy’s (exact–wearing size S/M)
Shoes: (similar)
Clutch: c/o Macy’s (exact)


If you’re looking for more dresses that you can do combo of fleece lined tights and a moto jacket with, check out some in the widget below:

black velvet leggings + colored sequins top + maroon velvet blazer + black booties maroon velvet blazer + colored sequins top + black velvet leggings + black booties colored sequins top + maroon velvet blazer + black velvet leggings + black booties

Velvet Blazer + Sparkly Blouse + (Velvet) Pants
Another trick I rely on to stay warmer in dressy holiday outfits is to wear velvet!  Velvet is luxurious and adds a rich texture that dresses up your outfit.  Velvet items also tend to be thicker, which keeps you warmer. 🙌🏽 Here, I’m wearing velvet blazer by INC that is made just for Macy’s and comes in 8 colors!  I’m wearing the color Port, but many of the jewel tones like Hunter Forest and Royal would be fantastic for holiday looks, too.  Or, go with straight black, of course!  See all the colors HERE.  I’m wearing size XS.

You could do this look with black jeans, black slacks, or ponte pants, but I went with velvet leggings!  They are VERY stretchy and very, very comfy.  These have faux back pockets, which I find helpful in smoothing out the rear a little. 😄  Check them out HERE.  I’m wearing size S.

For a stand-out outfit, I went this sparkly rainbow sequined tee by INC, which is only available at Macy’s.  Isn’t this thing amazing?!  It was kind of intimidating at first since it’s pretty bright in person.  But, I also LOVED the sass and vibrancy!  Pairing it with the maroon velvet blazer helped tone it down, and I ended up LOVING this outfit!  If a rainbow sequined top is still too much for you, there is a dark silver version that would be fantastic for classy holiday looks, too!  Check out both my rainbow top and the dark silver version HERE.  They’re 30% off right now!

Shop the Outfit:
Top: c/o Macy’s (exact–wearing size S)
Blazer: c/o Macy’s (exact–wearing size XS)
Leggings: c/o Macy’s (exact–wearing size S)
Booties: c/o Macy’s (exact–wearing size)
Clutch: c/o Macy’s (exact)


I hope this helps you dress up and enjoy your holiday parties without totally freezing!  Got any events to wear one of these outfits?



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