I’m pretty proud of my cocktail dress collection, but when it comes to dressy occasions that don’t quite call for cocktail attire, I sometimes find myself a little stuck. Last weekend, Dave and I went to my office’s Christmas dinner and then straight to a friend’s holiday cocktail party, and since I couldn’t settle on a dress that felt quite right for both occasions, I decided to play around with a shirt and pants combination that still felt really festive.

I wear this shirt nonstop in December–the black watch plaid feels just right for Christmas! Mine is sold out online, but this and this are similar, and these pants and this skirt are really cute too.
I bought these leather-front leggings at Target almost two years ago, but this was the first time I’ve actually worn them! I like the way the paneling makes them feel less edgy (considering I am the opposite of edgy ;)), and they were really comfortable–even after an Italian dinner! These and these are similar, or you can tone it down with just leather stripes down the sides (these or these).
No matter what I’m wearing, I don’t feel dressed up until I have lipstick and heels on! I’m wearing Revlon Kiss Me Coral, which is one of my most frequently worn shades. My shoes are brand new–they were a fabulous Christmas gift from my mom and I love them so much! The suede feels just right for winter, and the color (“Ornamental Red”) is the perfect shade of orange-y red that I know I’ll wear a ton with my neutral wardrobe staples. This color is almost out of stock in suede, but the new periwinkle version will be ridiculously gorgeous for spring, and the gray is so pretty too. (The glossy leather version, on the other hand, is fully stocked and so much fun.)
Black watch plaid shirt, leather-front leggings, d’orsay heels, bracelet, lipstick, nail polish

This was only the first of three back-to-back days of Christmas parties–it was a fun weekend!–and I liked this outfit so much, I ended up wearing a top and pants with heels for all of them! I like to give myself a mental pass during the holidays to experiment with textures and accessories that are a touch out of my comfort zone. As long as they’re anchored with classic pieces and a bright lip that always make me feel confident, I still feel like myself…just a little bit fancier :)