JENN! I love the little black dress. It is gorgeous on you. You look so glamorous!

You'd look great in something really different - like a velvet wide legged pant and tunic - you know, EF styles

Lisa, I have thought about something like that, but dress code is cocktail, and I think I’d feel too casual in pants.

You look fab in the LBD. I would not blame you for repeating it.

Tbh, I’d forgotten exactly what you bought instead of the dress. I’m glad you’re enjoying the tunic.

I’m the outlier here, I guess. While you look great in both pix, the outfit is my favorite by far. The shapes are perfect for you, and those textures....

If you wear the lbd, can you add velvet or other cushy, wintery fabric, maybe in a shrug or something around your waist (tricky with fit n flair)?

I'm all about separates, so I usually add a piece or two each year - sequins, velvet, etc., and remix. Regarding photos, I don't think I would be too concerned, myself. Then again, I am tall, so would be stuck in the back row and mostly hidden anyway. Unless the outfit is significantly stand-out and unique, would most people notice if it were repeated? And if they did (and in a catty way) that speaks more about them, I think.

I think the lbd is so fantastic on you, a true classic. Others have mentioned a statement necklace, velvet choker, and/or glitzy stockings/shoes to mix it up. Would you try a hair piece like a fascinator or blingy headband? Or some waist detail like a sash, ribbon, or thin metallic belt? Or make your wrap a bold swath of satin - magenta, turquoise, etc?

I've got a LBD, and a velvet jacquard legging, silver top combo I repeat. I might spend money on a wash and blow out at the hairdressers for the money I save by using a recycled outfit.

I'm another who thinks your LBD is fabulous and that you might want to just play with it.

La Belle Demimondaine has a really good attitude, I like everything she said and now that you've posted photos I would say you definitely can re-wear any of these pieces. I agree with La Belle that women look more at themselves in photos!

I think you look gorgeous but I don't like time travel backwards by wearing the exact same outfit so maybe new shoes? A necklace?

I relate this question to family weddings and events where there are always group pictures. I wouldn't mind wearing a quiet dress more than once, but am thinking of the last wedding that I wore a print and it stood out in pictures (not in a bad way I hope) and I won't wear that again for a while.
I would totally repeat a simple dress with a new sparkly jacket though.
Good luck with your busy season!

What an absolutely gorgeous dress that LBD is, and you look fantastic in it!

If I were in your shoes, and that dress looked that good on me, I would make a point of wearing it every year, but change up the accessories every time. Some examples: a velvet shrug; a white faux-fur stole; a long-sleeved black lace blouse worn underneath; a cluster of sparkly brooches; a contrasting belt, maybe rhinestone, or red patent with a bow. And I'd make sure those pictures documented my creativity for posterity!

YES. I get a new holiday outfit every year. I'm a fashion stylist! I remix my holiday pieces with casual items throughout the year though.

I pretty much never get a holiday outfit. We don't do parties often, and when we do there either family or 12 step fellowships parties where formality is not required. Sometimes I wish we did, because I like fancy outfits; but that would mean socializing, and I'm actually pretty socially awkward in real life.

Your LBD is fantastic!

To answer your question, no. I generally only have one dressy holiday event to go to, or none. During the rest of the year I may only be able to wear a formal dress again if someone gets married, which is rare.

I often dress up a dress that I can wear to work with fancier accessories for holiday parties. This year I MAY buy a new one but am not sure if that’s a wise idea or not.

Ok, hold up, Angie's solution is delightful AND super practical, so now I'm voting, yes, get something new IF it makes you feel more holiday and just remix the lovely pieces you wore before into regular wear.

The photo thing is a bit annoying. If it were my company party I might want
to wear something new. But for my husband's party, I am not sure the photos would bother me much - unless they were important keepsakes for us, like the only time of year we got dressed up or something. Assuming that's not the case, if I only saw the photos at the party, I would just try to assume that the other party goers are unlikely to be focused on what I am wearing as a spouse of an employee, and this is exactly the purpose of a simple black dress - to not stand out.

On the other hand, if you want to buy something, and maybe have a nice photo taken of you and your husband for your own use - go for it!

That LBD is so beyond fab on you that even though I generally like to mix things up, I think you could absolutely adopt staysfit's approach and rock it every year.

To chime in again and answer your original question Jenn: I don't buy a new dressy outfit every year. It possibly works out that I buy one every couple of years. I buy when I really like something that would fit into my wardrobe for more than one occasion. So when I get a wedding invitation, for instance, I generally have something suitable I can wear. I don't like that feeling of "I've got nothing to wear". I love your LBD, you look stunning in it!

Jenn that LBD is the bomb! Looks made for you.

I've seen metallic sparkly "sleeves" (forearm only) worn with dresses. It might be too casual for your event, but something like that with festive hosiery would change the look.

I am so appreciating all your thoughts, advice, and experiences. L'Abeille and Sal, your suggestions were particularly helpful to my thought processes. Sal, I loved that dress you wore this winter with the fur coat. I'm leaning towards doing a similar look with fishnets and a faux fur stole/wrap. And I'll do my hair up, which will change things up.

None of the photos from these events are formal... they're all candids and photo booth snaps. Other than that, it's a dark jazz club, so the exact details of the dress won't stand out. I do notice and remember what other women wore in the past, but I realized I'm not bothered if other people repeat at all, so why should I assume anyone else cares?

I like Angie's advice, but also think that if you have something that's fab on you, then you should wear it again (and again) if you feel like it. Just change up the accessories.

I've worn the same outfit to my office holiday party for 3 years (or maybe it's 4 years) in a row and no one ever noticed. This year I'm finally going to wear something different.

As far as you being all about functionality and repetition, maybe you could hold back a new purchase and make this party be the place for the debut of new pieces.

If I had holiday parties to go to I'd probably take Angie's approach, especially as I have the magpie gene and happily wear glitzy things year round (and winter seems to be the best time to get those pieces). You have a little magpie too, don't you? Could be an occasion to add something that you'd continue to wear later. That said I am glad to hear you're considering the LBD with a faux fur stole, as that's exactly what I was going to suggest after seeing how gorgeous you look in that fabulous dress! You've got some great options to pursue.

BTW, and I know you are busy so don't reply if a hassle, I wonder what did make you decide against the Sundance dress in the end, and what fabric it was after all, silk or rayon. I did like the dark floral tunic you bought that was a similar floral. I'm also curious as to whether you stalked the dress to see if it dropped in price.
My best ever stalking was some 2013 green sandals, looked like patent leather but actually synthetic, that I would not buy as never came down enough from original $150. Then in 2016 that shoe chain had a warehouse sale. There was my size for $ 19! 17 wears since then and summer has just started!

Jenni, I’m still stalking. I didn’t purchase, as it isn’t really all that practical for my lifestyle, but if it ever goes on clearance in my size, I’d still consider it. I’ve worn the other floral dress 7x in the month and a half since purchasing.

Our companies no longer have parties and not many friends do either. Finally ditched the LBD for something more comfortable and festive. Bought a cute wine velvet dress for holidays .. Me n hubs will do a few date nights n stay home for the holidays this year and kids will be coming home.

https://m.macys.com/shop/produ.....oryID=5449

Jenn, you look amazing in the LBD. However, if I thought that I was about to go to a function where they would show photos of what I’d worn previously I would change it up and find that as an excuse to buy something new. When it comes to LBDs accessories can make a huge difference. I also like having a little white and / or red dress to wear for special events.

This is my “special event” dress for the holiday season.