DH and are invited to an evening “ event” related to , probably, fundraising and similar support for an institution of higher learning & related to our church. It starts out in someone’s home and then moves to a restaurant. Not sure how many guests but assume a smallish group and intended to be more intimate & relaxed . I do not have a dress code report but expect it to be “casual “ in the sense of, not a community gala event, not cocktail attire, not even dresses likely.

We might not even go due to potential schedule conflicts but I started thinking about “ what to wear” and trying on a few things and found myself unexpectedly coming up short of what I’ve imagined in my tiny mind. Something “ dressy smart casual- no jeans with a twist of elegance and for evening “. So you know, not “ trying too hard”. It’s winter but we may have better weather around that time 50’s F maybe, , but for me I still need to feel cozy.
I would wear pants ( not jeans) and would want a topper or 3rd piece. Somehow I’m having trouble with trying to avoid too dressy outfits that are more “ party” vs too “ workwear” or daytime looks. My blazers and jackets look too work- like, not fitted or special enough, and my cardigans too ordinary. Might consider the EF vest but not sure.
I’ll try to show some “contenders” and “ what does this outfit need” when I have time. I may start with one or 2 best black pants options and build upward.
I find myself annoyed that I’m having the “ lot of clothes and nothing to wear” feeling, which may emphasize I have too many basics and not enough statement items, but I ought to be able to come up with something! Maybe items I hadn’t combined before, to juxtapose dressy with relaxed. Or with jewelry.

ETA: Here are some outfit tries. I first tried various blazers and jackets and could not get the look I wanted--too business-like or something.

#1: very dark photo but is a lace-over-beige peplum top with pants and a slightly fitted cardigan, and Munro boots. The boots are for warmth and to casualize the lace top. This is a DARK outfit though better IRL. I have to have both an underlayer and the sweater to wear this in winter, otherwise could wear the top alone.

#2-5 is black BR ruffle neck shirt tucked into lightweight Trouve pleated pants belted with sweater over. A semi-tuck is almost too "studied" for this situation but it sort of semi-hangs up on its own with belt. Bernard low block heel pumps are to dress up/juxtapose the sweater but I have to wear footless warm tights + nude-for -me kneehighs in cold weather. Shown with 2 shoulder bags; love my Sorel blush/burgundy but it's not a great contrast with the taupey sweater; magenta is very casual. I like this outfit and wore a version to work with loafers.

# 6-8 is EF vest and Theory tuxedo pants with boots. 6-7 with BR ruffle collar shirt untucked, and 8 with a round neck black top which allows me to wear shiny necklace to liven it up.

I do like the dressy pumps and the weather's warmed from 15 degress to 50, and it's mostly sitting/standing, but they are a bit marginal for me in winter and maybe a bit dressy for the group, though I don't know. The boots are, I think, "safe", not too precious, warm and good for possibly having to park a few blocks from destinations.

Both pants have zips at hems. The Trouve pants are shorter and can work with pumps or boots, but are rayon and need more underlayer. The Theory I had hemmed but left a half-inch below zipper end, to wear with higher heels for dressy event, but that makes them really too long, too much scrunch, for lower heels. I may get them re-hemmed to remove that last bit. I can hike up the waist a bit to shorten them also.

I have a favorite but would love to hear your thoughts! I would like more color; I do have a bright lilac Talbots cardi-jacket and some options for it, but maybe too much trouble for tonight.