I'm going to be what Angie calls "a mare" about this and insist that when your life doesn't call for dressy very often, this is when it's really important to keep that outfit in reserve.

If you dress up all the time, the likelihood that you will panic when a dressy occasion arises is low. It's those of us who live in jeans and boots who will not have a go-to source for dressy clothes, who will not own the right evening shoes, who will not own an evening bag, AND who will not be likely to own a dressy coat to go over your dressy outfit if your event falls in the dead of winter. (Ever notice how many dressy dresses are sleeveless? Not great when it's January in New York. And you're 53, with 53-year old arms.)

Janet, all your points are spot on, so I'm suggesting that it's important to keep the dressy outfit ready-to-go. Try it on, get it tailored if need be. Make sure you have one for warm weather and one for cold, if applicable. Get the right shoes and the right bra.

This is a fire drill, ladies. Don't wait until that heavy envelope shows up in your mailbox. Sure, you'll probably get a wedding invitation two months ahead of time. But there is no guarantee that in those two months, anything seasonally appropriate will be in the stores.

Absolutely right, April. Although my lifestyle is fairly casual, it's important to me to be appropriately dressed for any occasion that may crop up.
This probably sounds a bit morbid, but recently I've spent time and effort putting together a funeral capsule. If ever there were a time to avoid a last- minute- panic situation, that would be it, I think.

Going to be the contrarian here and say I don't keep the dressy dress on call. by the time I need it again it's out style. So I consign or donate.

I also learned my lesson on the "black pant" I have about 3 pairs that are either too big/small that I bought because

So you need to be aware of what you/I need more than anything.

I live within 10 minutes of the most shopping malls around so I am lucky that I can go shopping for what I need, so that is a factor as well

No rules

Chadya, this was me too. I used to have a formal dress because my grandmother felt it was important; ended up not even needing it for my HS or college graduations, never did get worn. I have some simple, streamlined dresses that can be dressed up or down. I have a dressy-enough black coat for winter events. My feet have gone up half a size since having a child, so my old dressy footwear had to go, practically unworn. Would like to replace those, but I have picky feet (and eyes!) so it takes a while to find something. Even in a simple frock with just a necklace and flats, I'm often the dressiest person at family weddings and memorials. If I needed a cocktail dress or similar, I would check the high-end consignment shop in my town first, and would use rental as a last resort.

DH is in a similar situation. The old suit his parents bought him roughly a decade ago is too formal for his industry, even for conferences, and now it reads as very dated -- like, "that one suit I bought just in case but never wore."

But see, LP, I think you're doing just what I'm suggesting, in a way that makes sense for you.

"I have some simple, streamlined dresses that can be dressed up or down. I have a dressy-enough black coat for winter events." And therefore you are ready for an event to come up. I wasn't. I didn't have anything that could sub in for an event, I was thrown into a panic, and my solution has been to keep "event wear" at the ready.

Where I live, "event wear" is significantly dressier than a simple, streamlined dress, which would be what I might wear on the daily, as the kids say.

Fair enough -- environmental norms are a big factor.

I just got my brocade pants shortened to a more fashionable ankle length...should last another 5 years.

Sometime in the late 90s/very early 2000s, I was in an Ann Taylor outlet with a friend and I tried on a black velvet sheath dress just for s&gs. Well. It looked stunning on, it was ridiculously marked down, and my friend convinced me that I would be a fool not to buy it. Surely I would need a winter cocktail dress at some point. That dress hung sadly neglected in my closet for years. When the day came that I had an event that I might have worn it to, I'd lost a little weight and it was now too big. I eventually donated it with the tags still on. I hope someone somewhere eventually wore it, because it was a beautiful dress.

I feel like keeping an outfit in reserve that you may or may not need for a couple/few years works much better for people whose weight does bounce up and down 10-15 pounds routinely. It's why when I recently bought the dress I've mentioned in other threads to fill the "conservative semi-dressy occasion in freezing weather" hole in my wardrobe, I went for a sweater dress, knits being much more forgiving of weight fluctuations than, say, dress pants or a blazer. And it's why I won't buy another cocktail dress "just in case", no matter how tempting.

AH, I do see your point.

Part of mine was "make sure the dress-in-waiting always fits" -- so if your weight changes a lot, try that dress on seasonally!

Hah! Dressy clothing for me is close to never wear for me, but I have a beach wedding to attend in 2018. Or at least I do unless they discover that it is not feasible. I have two dresses from 2012 that might work if they still fit; one fit'n'flare and a jacquard sheath they end up in a church. I just don't have dressy events in my life and pretty is not my style.