This year I have two non-kid holiday parties to go to – like with other IRL grownup women, in stylish homes! I don’t think I’ve needed to dress up in anything beyond a holiday sweater since I lived in LA, and I miss it (we host 2-3 holiday parties/potlucks, but they are all in our home and with a ton of kids so more in the “ugly sweaters and slippers” realm which is fun in its own way). So yes, I get to dress up a bit, but I still need to be comfortable while sitting, and I still live in Portland (meaning, it’s inherently casual – no body-con sequin dresses needed). So in my attempt to be comfortable, casual, but cute in a slightly more cocktail attire way, I put together a few looks with “holiday-adjacent” clothes. Kaitlin wanted to shoot this with flash, like I’m at a party, which sounded fun to me, so you are about to see me fake drinking ginger beer by myself mid-laughter…I made some choices, folks!

Sweater | Skirt | Tights

This first one was Brian’s favorite – I hadn’t heard this level of outfit enthusiasm in a while (probably because I mostly wear sweatshirts and barrel pants). It’s definitely giving Martha in the 80s with the preppy sweater and bows (with the skin showing through the gaps). Then I paired it with a tiny pleated skirt that is so well-tailored in a plaid that feels really me. I suppose it’s my attempt towards the “Ralph Lauren Christmas,” but in a way that fits my style more. I bought the skirt and tights from Aritzia and am really loving the burgundy with the green/blue plaid. I bought the shoes from a consignment shop like 10 years ago, so sadly, I can’t link them. Oh, and I’m wearing a large in the sweater (the only size left at my local Target), which fits great as it’s pretty cropped.

Sweater | Skirt | Boots

This sweater is the softest of all of them, and I obviously like that the blue can be carried from fall through winter. The fair isle style of it gives “holiday,” for sure. But man is it comfortable, soft, and warm. 10/10. I paired it with a Sezane wool skirt and boots I’ve had for a few years (both still available). My concern here is if we have to remove our shoes (which is typical in Oregon homes). This outfit doesn’t work without the boots. Not sure what the current “house party” protocol is for shoes on/off…my feelings are that if it’s a casual party with a ton of kids, fine… shoes off – but if it’s any sort of adults-only dress-up party, shoes should be allowed, right?

Sweater | Pants

Another “conservative up top, a bit scandalous on the bottom” look. This cable knit puffed sleeve sweater has a really good cut – it’s wider at the bottom but still short, which is nice for the proportions (big puffed sleeves + long is just too much volume for me). I’ve had the pants for a while, and they are questionable for sure – super tight and flare-y at the bottom, so styling is key here to not look super cheesy.

I think this outfit could use a pop of burgundy – maybe a bow in my hair or shoes? But I felt good in it, the pants are splurgy (but are on sale right now!) and very flattering.

Cape | Skirt | Tights

Here she is, super sophisticated! A new company named Alice Walk reached out to send a few things with no obligation. Usually, I decline, not wanting more stuff I might not wear. But this cape is so beautiful that I wanted to see it in person – and it’s extremely well-made and pretty. It comes in a few solid colors as well, but of course, I was drawn to this pattern. It’s definitely splurgy (think Frank & Eileen vibes), but for someone with an office job that wants to impress, I think this is fantastic to wear around a city.

This is my first foray into the slip skirt (I know this trend has been around for a while, but this one stood out to me). It’s a gorgeous blue with black lace, and with the tights underneath, showed no bumps (this was my fear with these silk/satin slip dresses -they can show everything if not well made). I picked this up at Nordstrom, not realizing how expensive it is, but I know I’ll wear it as it’s easy to pair with sweaters for a pretty/sexy/sophisticated look.

Cardigan | Skirt | Tights

I was so comfortable in this outfit and felt pulled together in a way that I usually am not. The cardigan (also from Alice Walk) is so pretty, soft, and well-made, with pretty horn buttons. I really liked this tonal look, with the burgundy tights giving it a bit of an edge.

Pearl Necklace | Gold Pendant Necklace

I think for the party, I would likely add more layered jewelry, but this felt like a solid holiday house party outfit that checks all the boxes while being so comfortable.

Cardigan | Shirt (similar) | Leather Skirt | Tights

A fantastic burgundy cardigan that says holiday, without being bright red. I added a pop of black and white stripes, leather, and sheer black tights. BTW, I’m on a hair journey and trying not to get any highlights (it’s been a full year since I last did), so I’m doing just root touchups for now. I like being less bright blonde, but these photos are making me want to just get a few pops of brighter blonde around my face…

Sweater | Skirt | Tights | Belt | Boots

Another holiday adjacent sweater (fair isle) that is so comfy and easy to wear. I paired it with the J.Crew mini skirt, burgundy tights, and boots, but obviously so easy to dress down (leggings, denim, anything). I’m wearing an XS, so it’s pretty oversized. But super soft and lightweight – so easy to layer over or under.

Let me know if you’d want some casual/comfortable NYE looks. We always go to a family house party, but I typically wear something sparkly because I’m extra like that (while still being comfy). xx

*Photos by Kaitlin Green