Angie - thank you for patiently adding more advice. I will keep your suggestions on hand and see where I get with it. I think 2 complete outfits is the way to go. The larger capsule seems more than I would need. Cream is another great colour to consider. I bought a pre-loved BCBG Max A asymmetric zip-up vest thing in cream awhile ago and it might fit in somewhere. What do you think of metallic footwear in my case?

You have a great eye Lisa so don't lose confidence in your style choices which are always on point.

I think a metallic mule or elevated loafer or flat could be a great choice. Those along with some earrings would make even a black (I know you don't want black) top and pants feel more evening.

I agree, browsing does put those wild card options in front of us, but for some people it is not an option any more due to the lack of choice locally.

Do you still have those hot pink mules you got a while back for your holiday at-home? I thought they were pretty fab - and memorable, as you can see!

Bronze footwear to bookend your darker hair?

Ooh, Carla's got some great ideas. Bronze footwear would be fabulous. And if you can't find it this year, I bet it will show up next year, as the browns become fully established at retail. Would work with the right green, or burgundy, or navy...and I can really see you in a tonal outfit -- the pieces could be mixed and matched with more casual items at other times. As Sal says, you have a great eye and know your own style and have always looked sensational in the holiday outfits you've posted in the past.

I love the Naturalizer slingbacks -- can wear them for dressy or a bit less dressy. But they don't work for me in winter. Could work ok in a climate where you wear boots to venue and remove/ change shoes, though. Probably too classic/ ladylike for you, but the comfort is there for sure and they work surprisingly well with different types of outfits, so something like that -- metallic but a fairly flat shoe -- could feel less precious than a heel.

Also, you are right about shopping -- it is not the same since Covid. There are still a few boutiques and second hand shops here in Victoria, but most other options have disappeared. I have to go to Vancouver. Or online. Which involves more risk and sometimes cost.

One thing I did is buy a tulle skirt in burgundy and a pair of black velvet pants. I wear both with dressy boots and an interesting sweater or top. This has worked very well for me. I have seen some burgundy velvet pants lately. It might work for you. You always look very put together so I don’t think you will have a problem.

I'm nodding along with much of the excellent guidance on this thread! Fabbers are sooooo fab!!!

LJP, my pleasure, and two complete outfits are easier to pull together than a small capsule. Over time, you can build onto that part of your wardrobe, if you like. Irina, Janet, Suz, Carla and Sal have successfully done just that in the time that they have been on this forum. We saw it happen!

I suggested trousers because you're not as much of a dress or skirt person. Not black, and YES to metallic shoes. Any metallic. I think you wear it all! I'd keep them closed if your're after one pair. More versatile. Sandals might be your preference, but they are not year-round-shoes. (As Suz, mentioned).

My own dressy capsule is curated, and there are lots of modern classics. Simply because I don't tire of them, and I enjoy wearing them! I've had some of the items for 13 years! The gold shoes, the faux fur capelet, navy tulle skirt, short lace dress, jumpsuit, and cream Fulra are old! I feel great in them, they are gorgeous quality, so I continue wearing them with a happy heart. I also dress many items up and down - wear them with jeans and more casual items - and throughout the year. Lots of mix and match options.

I added the gold cabled polo sweater and cream lined trousers this year.

I find trouser suits very useful! Dress them up and down, and insulating. I can style them with many tops. I have two - burgundy and brown.

I also got every item on sale, and many off-season. Far less pressure that way, and cost-effective.

Anyway, didn't mean to write another novel! Hope this was helpful in some way

And your "cream asymmetric zip-up-vest-thingie" sounds like a great start to your dressy outfits!

It is get much harder than in the olden days for me to have a reliable dressy “ capsule” because I don’t trust my feet, or body shape changes, for longevity even if the clothing items are themselves rather timeless. Plus one promos is seasonality. I’m very temperature- temperamental, not a good all- season dresser and so sometimes get caught with summed vs winter event. Though in general, F/W is more likely for dressy events.

But one thing that Angie mentions resonates with me. It is more useful for me to have complete outfits even if only 1 or 2- including footwear — than to have random things I think I will just mix and match. That is because I’m very proportions-picky ( long over lean, boxy or fitted over full) and footwear matchup.

It doesn’t mean I won’t COLLECT an outfit, but just more, I have to have a goal and get the pieces or change goal.

Got my metallic heels, which seem so specific, but somehow managed to go out in many ways. That is a great shoe to have around.

People love their metallic shirts, and their black dresses for holidays. If I were going to an event like this, though, I might get a richly colored shirt, like a deep green blouse. Or any comfortable dress in a current cut. Pants would be acceptable, but if I planned on dancing, I would do a dress or a skirt.

Lisa I really feel you here, on both the introvert and I-have-nothing-to-wear-anyway counts.

Somehow dressy/occasion clothing seems like it can often operate as a vicious cycle: I have a casual lifestyle, so I haven't really prioritized building a functional dressy capsule, then when an event comes along I cobble together something ho-hum, then I feel like I don't really know how to dress for occasions and there's no point in bothering to invest in this area of my wardrobe anyway, and the cycle repeats.

Anyway, the point is not woe-is-me but just to commiserate. You have gotten really good advice. I like the idea of building two complete outfits, going for a tonal look, and metallic footwear (for you and me both -- so thank you for the inspiration!).

I think for me a key piece of the puzzle might be some really large-scale statement accessories with a modern twist. Just offering that thought in case it sparks some wheels to turn for you as well.

So many great suggestions here. I will add that I think a little bit of avant-garde can be a great way to go, too. An "occasion" can be a time to wear something that you own and love but you feel is a little much for daily life and errands. I have a few pieces from OSKA that fit into this category: a pair of pinstriped wool flannel pants that are pieced with different width stripes in a subtly arty effect; harem pants in felted wool knit with raw edges; a bracelet-sleeve swing jacket in crinkled wool. None of these screams "holiday," and yet I've worn them on holiday occasions, with tops that feature silk, cashmere, or matte sequins, a bit of sparkle in some jewelry, and stompy boots, pointy heeled boots, or various pumps.

Wow, I loved to read all this thread, with so many solutions and ideeas to consider. And, I feel your pain-but like merwoman said, I would rather say YES simply because of getting a new experience itself. You don't have to attend all event to the end-so if it is ovewhelming your introvert self at a moment, you can always leave earlier-but you may also have some FUN!

I think showing some bare arms or shoulders (less cleavage!) is a good way to do dressy on some kind of events. I like it on youngers and even older girls who have the body to do that with confidence and dignity- so other than that you don't really have to dress very different to your normal style I think.

I can't do that anymore and I didn't want to be caught unprepaired so I have my fair amount of dressier items for this kind of life demands. I also am very picky of my dressy outfits to be suitable for the exact venue itself and I no way like to stand out by overdressing. But that doesn't mean I don't like to make a statement (in a good way) with my oufit and I would totally aim to feel good in it. We like to dance so a good shoe and a midi hem is crucial for me.

For the last New Year Eve (all night eating and dancing event with larger family and other folks at a fancy restaurant) I went with an olive background and small devorée black flocks tulle skirt, a more substantial black jersey V neck cami and a shorter open style black sequined flowy topper with the long sleeves scrunched up to the elbow-so that felt immediatelly not so dressy or fussy anymore. I was so happy about the arm coverage and the elasticated waist of the tulle skirt:-). (I wore a black matte buckle elasticated belt to hide the elasticated waist of the skirt itself without compromising comfy but my jersey top had the perfect length for just covering it so it was only visible maybe when dancing gone mad:-)).

I wore black sheers (which I always preffer to skin color) with a pointy toed, black matte suede low block heel and thin ankle strapped mary jane (something like Angie's gold shoe) with a flexible(!) sole, so it was the perfect dance shoe for me.

For You I think will indeed rather aim to do another monochrome/tonal than black and not really glitsy. Say artsy or an architectural but minimal cut matte/or subtly satiny shine something. High expectations, I know, but I trust your eyes and am sure you can find something fab over the next year, if you feel inclined to build up an outfit! Think rather to a gallery opening outfit than the common Xmass kinds. Wish you luck!

ETA: Oh, I see Sharan above said the same thing...

On the footwear front, I've found these Madewell mary-janes to be the solution to all my festivity woes. They are sparkly but still function as neutrals, and something about the toe shape and heel height seems to work with just about anything -- I've paired them with everything from corduroy trousers and cardigan for a daytime holiday party to a silky ball skirt and tailored gilet for an outdoor-formal wedding. And they have a thin rubber sole with decent traction compared to a lot of dressy shoes!

I picked up a comfortable sequined longer pencil skirt that I pair with a soft sweater in the same colorway. Festive, comfortable and feels like me.

I have to say that I never considered a dressier metallic shoe until this post. I never saw them as something I'd wear . But I'm warming up to the idea quite quickly !

And as for sounding like an awkward introvert, that's not so much the issue as is socializing with my coworkers. I see them every day and have no desire to do so on my own (valuable) time . I am fine in a big party with lots of people I know, but the days of entertaining among friend groups seems to have ended with Covid and never recovered. We used to host a big holiday cocktail party at our house/and then condo, but we've even stopped doing that. Half the fun of that party was planning my outfit !

Anyways, more thanks to those who have commented - I'm on my phone and can't comment individually. I'm getting my hair coloured tomorrow so maybe that'll spark some holiday spirit too :).

I saw a gorgeous/the perfect outfit on a hairstylist from the UK (IG called Silver Kat) - it was a longish black skirt with a back slit showing a white layer of some kind underneath, and a black leather jacket and pumps (eek) . If I could duplicate this look.....

I have a house holiday party coming up and have yet to figure out what I will wear. No young uns, no Gen Xers and maybe one Millennial. I think the majority are retired. I asked and was told it’s a Shoes Off home so I don’t have to worry about footwear, just the length of pants should I decide to wear them.

Shoes off for a holiday party ? Yikes . The hosts need to relax a bit . There’s nothing worse than a bunch of people standing around in their socks having cocktails and canapés . Ruins the whole look of an outfit .

The host talked about buying disposable booties for us to wear. I am thinking those hazmat things? My feet scream without padding so I may pack nonskid slipper socks. Thought I would give you more eye rolls lol.

I'm late to this thread but wanted to chime in. As an introvert I'm not a fan of company holiday parties, or anything that begs for volun-told participation. Unfortunately, as part of the leadership team, not going is not really an option for me.

My solution has been to wear my business clothing on the bottom half (black trousers, black heeled boots) paired with a "fancy" item on the top half. In the past my tops have been lace, satin, or sequins in black, white, or jewel tones, which jazzes up the business wear without having to resort to purchasing dresses or skirts that I'm only going to wear once a year to a company holiday party. I've never had a need to build out a large dressy capsule so having only 1 or 2 dressy tops that pair well with my solid bottoms has worked well for me.

Dressy here mean a wide range but often dark jeans and a "nice" top with some jewelry and maybe ankle boots. Or a fringe suede vest.
I guess I'm lucky in that as I don't like formal style dressing. But that said, I'd probably check out the venue to see what usual evening attire is worn there normally, and if it's not overly dressy, I'd likely go and just choose what I'd wear based on if I were going there on my own accord, like for a nice date night. No special shopping required. But that's me.

Many people will be panic dressing for these types of events I'll bet and they will often end up uncomfortable all evening, whereas if you wear what is "normal nice attire" for you, you will be comfortable in your own skin and probably be smiling while you're watching them fuss with their new clothing.

Wow, love it too!(Silver Kat's) but part of her outfit (and is an important one) is her white hair, matching the underskirt showing...just saying:-))