Great skirt! Does the grey topper from 1 work with the tops from 2 or 6?

I do prefer a dress rather separates just because it's a wedding, so err in the side of being dressed up rather than dressed down. Of course, if it's a casual wedding, then my favorite separate outfit was #1.

The dresses with the grey topper and jewellery win in my book(!) Any of the shoes.

OOOH! More options! Fab!

From your THIRD set of pics here:

I like #2, 3 and 4 for the wedding!

I like the black dresses best with a slight preference for the sleeveless one. You can do so much with a black dress.

Agreeing with Angie's comment just above, from the 3rd set of pics - #2, 3 and 4.

That velvet jacket really is gorgeous!!

Though I guess I'm still stuck on the idea of a dressier shoe - relatively that is, of course. Something with shine or sparkle, patent maybe? Flats of course for comfort. Boots just feel a bit too casual for me.

Honestly, while a dressier shoe might be ideal, with the longer black dress and velvet topper, no one will be looking at your feet. The black boots blend in with the black dress and they certainly don't stand out. I also really like option two from the third set of pictures.

Thanks again everyone for commenting and offering comfort and suggestions! I really do have to rely on a mix of creativity and chutzpah to get myself together for this one.

I brought home a pair of patent loafers that I will try with a couple of things. I also brought home a *few* (that's an understatement) new contenders -- still looking for that magic combination that feels 'right' -- elegant, comfortable, not fussy, not too hot...

I'm with citygirldc in that I think dresses look more dressier at a wedding. I like the 2nd dress and think it would be fine for a wedding.

I really like the sleeveless dress with topper in pic#2 in last batch of photos. I think the boots work well for a fall wedding

There's the rub. I have lost 30 pounds so far this year, and I was hoping to get to something better than fine. I wanted to look and feel great, and I don't know that any of these makes me feel great.

The footwear you listed in your original post sounds really cool; you could make some slick outfits with any of them, imho. Look at Sally and Brooklyn’s posts. I’ve lost weight in recent years, so totally get you wanting to flaunt it at the wedding. Go for it!

I like the black dress and also the skirt and flowered top. The dress could be dressed up with a necklace. Your shoes aren’t critical to the dressiness of the outfit. You’re aunt of the groom, so no one expects you to go buy a new outfit and accessories. This is based on my experience. I live in the west, though, so take it with a grain of salt.

Carol I am sorry I am late to this thread and also just starting my first morning coffee but I have to say you have presented so many fabulous outfits here my head is spinning! I think the black dress is probably the way to go for the wedding (least worries and looks wonderful on you) but the first set of outfits is fabulous and you must wear them somewhere. I love the jackets, the florals, everything! Will take another look after I am more awake .

Thanks, Stagiaire Fash. I have gotten into way too much churn here trying to fit a standard for which I have neither the tools nor the temperament. I am guaranteed to "fail" if success is measured by my ability to wear a dress and heels.

So here I am churning away -- ! I have tops I like, but they don't go with the bottoms. Bottoms I like, but the tops don't work with them. Toppers I like that don't feel right with any of the other pieces. Shoes that don't really suit any of it.

(I miss the look of party shoes, even if I don't miss the feel of sore feet.)

If you want to still wear loafers/ Oxfords/ boots, have you considered attaching shoe clips ? Just to add a little bling without sacrificing comfort (attaching an example). You could also add a brooch to your jacket.

As for separates, are you able to do column of colour - e.g. grey top & trousers, black top & skirt? Or with the burgundy jacket in your original photos, do you have burgundy bottoms? That might look more formal.

Also if it's an indoor wedding, could you get away with rolling your cuffs/ showcasing a little ankle with your Oxfords/ loafers? I feel that usually helps to add a chic 'styled' element to such menswear 'with a twist'.

Those clips are cute Zaeobi -- I wasn't even aware of such a thing. I'll have to see if I can find some! Thanks for the idea.

And just to put it out there -- it's not that I want to wear oxfords, it seems to be all I CAN wear on my feet!

Thanks, Shevia -- it seems I can do office looks until the proverbial cows come home, but I am stymied on the dressup front!

I so didn't want to wear that sleeveless black dress again. It is old and has always just been "good enough". I wear it because it meets the requirement, but I have never felt particularly good in it. It won't kill me to do it again, but it won't thrill me, either. Sigh.

Right, when I say 'want' I meant wanting to SYC (rather than buy something new). I do understand the struggle - even most Clarks don't fit my wide forefoot (yet narrow heels), medium arched, high instep feet well!

Could you jazz the sleeveless dress up with a nice topper (maybe the burgundy?), or even a belt/ sparkly stole (pashmina/ throw)? I know it can be disheartening to wear something 'good enough' again, but don't forget to keep your eyes on the prize! In the long run, it will be worth saving the money now to buy something truly *fabulous* once you reach your goal. Eyes on the prize!

From your third set of pics, I think #2 and #4 look really great on you and would be appropriate for a wedding. Both outfits are chic, the footwear looks ok, and the beautiful topper adds some life and pizzaz. To my eye, it is always good to avoid too much black in a wedding.

Thanks, Zaeobi - New shoes are an option, but they have to be oxfords or flat boots. The burgundy shoes are new (on order to a local store). I could exchange the for plain black ones.

I have been trying, but there just aren't a lot of options available in my market that work for my for my wide forefoot and narrow heel. But the clips are a cute idea to try to spice things up!

Your point about keeping perspective is also well taken. Thank you.

I think that seeing you really don’t want to wear the dress in the third set of photos, that the dress in the second set of photos looks really good with the V neck at the front and the necklace you have on in that set. It’s newer right?- you didn’t get to fit it before you outgrew it? I prefer the Oxfords- the black ones are nice but if the burgundy fit and are comfy when they arrive they would perhaps be nicer, to bring in another colour. Then you could pick from your beautiful grey/silver topper or the burgundy one, and you would surely be looking pretty dressy by then?
I understand your not wanting to wear the dress you’ve never liked that much and that you’ve already worn several times.
I know it’s a nephew not a child but you still want to feel good, I can relate to that very well.

Thanks, Jenni. For sure no one is there to look at me. I was hoping for something that the oxfords would feel more deliberate with, and one never does think sparkly dress and oxfords!

The upside is that I do have options, so I won't have to attend in my bathrobe! Being very plain, the newer dress feels somewhat more in line with the plain shoes. But there is something to the fact that bare shoulders are better for a gal my age if there is a bit of dancing allowed. (I checked our public health orders last night and it sounds like masked dancing when all are fully vaxxed is allowed now).

I've started a new thread here with what I think will be my solution!

Love that first jacket and the shape of your skirt! Agreed that dresses (or jumpsuits, or suits) look dressier than seperates.
Seperates to me are daily work wear rather than dressy.