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GenZStyle > Blog > Shopping > Dressing Up Holiday Sweaters For A Party (While Still Being Comfortable)
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Dressing Up Holiday Sweaters For A Party (While Still Being Comfortable)

GenZStyle
Last updated: November 22, 2025 6:35 am
By GenZStyle
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Dressing Up Holiday Sweaters For A Party (While Still Being Comfortable)
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There are two non-kid holiday parties this year. It takes place in a stylish home, just like the other IRL adult women. I don’t think I’ve ever had to dress up in anything other than a holiday sweater since living in LA, and I miss that (we host a couple of holiday parties and potlucks, but they’re all at home and we have lots of kids, so it’s more in the fun “ugly sweater and slippers” realm). Yes, you can dress up a little, but you need to be comfortable while sitting, and I still live in Portland (I mean, Portland is casual by nature, no need for bodycon sequin dresses). So, I’ve put together a few looks using “holiday-like” clothing to keep things comfortable and casual, but still cute with a little more cocktail vibe. Caitlin wanted to photograph this with flash as if I were at a party. That sounded like fun to me, so you can almost see me laughing and pretending to be drinking ginger beer by myself… I made some choices, guys!

sweater | skirt | tights

This first costume was Brian’s favorite. I haven’t heard this level of costume enthusiasm in a while (probably because I mostly wear sweatshirts and barrel pants). It definitely gives the Martha of the 80’s. preppy sweater and ribbon (You can see the skin through the gap). Then I paired it small pleated skirt It’s made with a plaid pattern that’s just like me. I think this is my attempt at a “Ralph Lauren Christmas” but in a way that is more in line with my style. I bought a skirt, tights I’m from Aritzia and I really like the burgundy with the green/blue plaid. I bought these shoes at a consignment store about 10 years ago, so unfortunately I can’t link them. Oh, and I’m wearing a large size in the sweater (the only size left at my local Target), and it’s pretty cropped so it’s a perfect fit.

sweater | skirt | boots

this sweater I like the blue color, which is the softest and can be used from fall to winter. Fair Isle style certainly gives you a “holiday” feeling. But it’s comfortable, soft and warm. 10/10. I paired it with cezanne wool skirt and boots I’ve been using them for several years (both are still available). My concern here is whether I have to take my shoes off (which is common in Oregon households). This outfit won’t work without boots. I don’t know what the current rules are about wearing shoes or taking them off at “house parties”…my feeling is that if it’s a casual party with a lot of kids, it’s fine…please take your shoes off. But if it’s like an adults-only dress-up party, shoes should be allowed, right?

sweater | pants

This is also a “conservative on top, a little scandalous on the bottom” look. Cable knit puff sleeve sweater It’s a very good cut. The hemline is wider, but still short and proportionately good (large puff sleeves and long lengths are too voluminous for me). i had pants For a while, and they’re certainly questionable – they’re very tight and flared at the hem, so styling here is key to not looking super cheap.

I think this outfit could use a pop of burgundy – maybe some ribbons in the hair or shoes? But I felt good wearing them, and the pants were luxurious (but… Now on sale!) And very flattering.

cape | skirt | tights

Here she is, very sophisticated! A new company called Alice Walk reached out to send some things with no obligation. Usually I say no because I don’t want any more things that I might not wear. but This cape It was very beautiful and I wanted to see it in person, it was very carefully made and very nice. There are some solid colors available, but of course I was drawn to this pattern. While it’s certainly luxurious (think Frank & Eileen vibes), I think it’s perfect for wearing around town if you want to make a good impression at the office.

This is my first foray into a slip skirt (I know this trend has been around for a while, but… This one It stood out to me). Gorgeous blue with black lace, tights There were no bumps underneath (which is what I feared with these silk/satin slip dresses; if they weren’t made well, everything could show). I bought this at Nordstrom and didn’t realize how expensive it was, but I plan on wearing it because it’s cute and easy to pair with a sweater for a sexy, sophisticated look.

cardigan | skirt | tights

I felt very comfortable in this outfit and felt united in a different way than I usually do. cardigan (Also from Alice Walk) It’s super cute, soft, well made, and has cute horn buttons. I love how this tonal look gives the burgundy tights a little edge.

pearl necklace | gold pendant necklace

I know I’ll be wearing more layers of jewelry at parties, but this felt like a solid holiday home party outfit that checked all the boxes while being super comfortable.

cardigan | Shirt (similar) | leather skirt | tights

amazing burgundy cardigan It is not bright red but indicates a holiday. Add a pop of white and black stripes, leatherand sheer black tights. By the way, I’m training my hair and trying not to get any highlights done (it’s been a whole year since I last got them), so for now I’m just doing touch-ups at the roots. I like blondes that aren’t too bright, but these photos make me want to put a little lighter blonde around my face…

sweater | skirt | tights | belt | boots

another holiday adjacent sweater Very comfortable and easy to wear (Fair Isle). I paired it with J.Crew mini skirt, burgundy tightsand bootsbut obviously it’s very easy to dress down (leggings, denim, whatever). I’m wearing an XS, so it’s quite oversized. But it’s so soft and lightweight that it’s easy to layer over or under.

Let me know if you want a casual/comfortable NYE look. We always go to family house parties and I tend to wear something sparkly (while still being comfortable) because it’s special. xx

*Photo provided by: caitlin green

Source: Emily Henderson – stylebyemilyhenderson.com

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