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188 Comments

Black Tie Optional: 3 Holiday Outfits

Well, my big event is this weekend! As you may recall, I’m attending my husband’s company holiday party in Chicago, and I’ve been ordering and trying cocktail dresses like it’s my job.

And I guess it sort of is. Considering that I’ve made a business of sharing my personal style online and helping everyday women like me figure out how to dress appropriately for any occasion so they can feel good about how they present themselves to the world, I feel a little extra pressure to “get it right” for this particular event.

Plus, I just think it’s fun to shop and come up with “the perfect outfit” for any big occasion. Which, I guess is how I ended up with a fashion blog!

Eliza J. Faux Fur Capelet (S) // Norma Kamali Strapless Midi Dress (M) (more sizes) // Sam Edelman Kia in Gold (8) (also at Nordstrom) // Loeffler Randall Rhinestone Baguette Bag // Ettika Crystal Chandelier Earrings // old Victoria Emerson bracelet c/o // J.Crew necklace

In my last Try-On Haul, where I first showed you these three dresses, someone suggested that I style each one as if I’m going to the event and share them with you all and let you vote.

Even if I didn’t have this blog, that is exactly what I would have done, and what I recommend you do whenever you’re trying to make a decision between several outfits. So here we are!

The Considerations

When planning an outfit for a big event – or for any reason, really, but especially when it’s an event where I will be meeting people I don’t know or don’t see very often – there are a few things I try to keep in mind.

First and foremost, who is my audience? Not that it really matters what people think of my outfit, but I feel more comfortable and confident when I feel like I fit in rather than stand out, so I always consider where I’m going and how others will be dressed.

The other thing I try to keep in the forefront of my mind are my personal style goals. I want my outfits to look modern, polished, and understated whether I’m going to the grocery store or to a gala.

It can be tempting to dress for a different style persona when attending an event that is outside of your typical routine, but it’s more important than ever to be true to yourself in those situations, so you feel comfortable and confident and authentic in how you present yourself.

And finally, I want to be comfortable. Meaning, I don’t want to wear something I will have to fuss with all night, and I would rather not be excessively hot or cold. Although for this event, I’m willing to sacrifice a little bit of comfort to love how I look.

The Contenders

After trying on many dresses, I’ve narrowed it down to three… actually, two, but I’m sharing all three finalists here today because I have the photos, so why not use them?

Plus, it gives us an opportunity to discuss how I decided to accessorize each option, which is something many women struggle with.

First up, this Norma Kamali Strapless Midi Dress.

Norma Kamali Strapless Midi Dress – 25% off (M) (more sizes avail) // Sam Edelman Kia in Gold (8) (also at Nordstrom) // Loeffler Randall Rhinestone Baguette Bag – 25% off // Ettika Crystal Chandelier Earrings // old Victoria Emerson bracelet c/o // J.Crew necklace

I love this dress for its simplicity and understated appeal, and it’s way more comfortable and figure-forgiving than it looks.

The fabric is high quality, and I feel like it looks like I just pulled a dress out of the back of my closet at the last minute and threw it on and made it look fabulous with modern accessories. You know, kind of like… Oh, this old thing??? LOL!

But that’s also partly what’s holding me back from wearing it. I know that I did buy this dress with this event in mind, and while I like it more than I ever imagined I would, it still seems rather plain in comparison to most of the other options I tried. And accessorizing it has turned out to be more challenging than the others.

First, let’s discuss my jewelry choices. I tried the dress both with and without a necklace, and I like it so much better with a necklace. I feel like this J.Crew square faceted crystal necklace set in gold tone metal is perfect. It’s oversized and modern, yet in keeping with the simplicity of the dress.

I also wore crystal and gold statement earrings that I feel coordinate with the earrings but don’t compete too awfully much, although I wonder if a simple stud would be better.

And then I grabbed an old mixed metal cuff out of my jewelry box, but I don’t love it. If I were going to wear this dress to the event this weekend, I would want to come up with something else.

Because it’s so bare on top, I wanted some type of covering that I could wear inside if I feel I need it, so I pulled this faux fur capelet out of my arsenal. I’ve had it for a few years, but it’s still available, and on sale at Bloomingdale’s!

I like the look in theory, but I wonder if it leans towards matronly, and I also find it awkward to keep on my shoulders.

When it’s fastened, it looks more like outerwear, and when it’s unfastened, it feels like it’s going to slide off at any moment.

I’m not sure I’d want to wear it inside, anyway, and if I don’t, then I’m back to feeling bare on top.

The other option is a sheer metallic wrap, and I just so happened to have this silver one from a wedding a few years back, so I tried it on to see if I like the look. (I’ve ordered the gold, so I have it if I decide I want it.)

I like that my shoulders are adequately covered, but it also covers up my waist and ruins the shapely silhouette that the dress provides, in a way that the fur wrap did not. Plus, the wrap is hard to keep in place, and I don’t want to be fussing with it all night.

Before I eliminate this option entirely, I’d like to try it tied the way the silver one is shown on the Nordstrom model and see if that works better, but I would still need another coat or jacket to wear to and from the event. It just seems like more trouble than it’s worth.

Okay, moving on! My second option is this one shoulder velvet sheath dress. I really like the combination of velvet and satin on this one.

The fabric combination seems like a good match for the formality of the event, and the satin foldover detail gives it the modern touch I need to feel authentic to my personal style, while still allowing me to wear my favorite sheath-style silhouette.

Eliza J. Velvet One Shoulder Dress  // Sam Edelman Kia in Gold (8) (also at Nordstrom) // Loeffler Randall Rhinestone Baguette Bag – 25% off // J.Crew bracelet & earrings – 40% off

I also really like the side slit, and although I feel like it could be a little shorter, I do like the below-the-knee length. It looks more formal than the shorter styles, and since this event is black tie optional and there will be some in floor-length gowns, I feel like this helps to walk that line of formality.

Also, Alison helped me figure out how I’m supposed to wear the satin foldover piece. I was wearing it on my shoulder, as pictured on the Bloomingdale’s website, and it was doing wonky things in the back. But she found another photo online where it was worn off the shoulder, as I’m wearing it here, and it looks so much better from all sides.

It’s also more comfortable than it looks. It stays in place when I move around, and it gives me just enough coverage to feel appropriate for a work event, but not so much that I feel frumpy.

This time I swapped out the shorter statement earrings for a longer pair, and I removed the necklace.

I really love these earrings, especially with this dress. I wish the clear crystal that I have wasn’t sold out. They’re lighter than they look because they’re on a fabric backing, so smart!

I also really love this square-shaped crystal tennis bracelet. I didn’t want to wear it and the matching necklace with the strapless dress, but since I’m not wearing a necklace with this one, I would definitely wear this bracelet.

I’m excited to add this Loeffler Randall Rhinestone Baguette Bag to my evening bag collection. It goes so well with these matte gold heels, and I know it will be nice to have in the future, as well.

It’s a bit of a splurge, but it’s currently part of the Blooomingdale’s Friends & Family 25% off sale, as is this dress, by the way.

The Eliza J. one-shoulder dress is probably my top contender at this point, but then there is this metallic sheath.

This dress has an entirely different vibe than the two above, and that’s what I’m unsure about because it’s a perfect fit, and I absolutely love it. I’m just not sure it’s the look I want to present at this event.

Vince Camuto Embellished Cap Sleeve Sheath Dress (10) // Sam Edelman Kia in Gold (8) (also at Nordstrom) // Loeffler Randall Bailey Pleated Clutch – 25% off // J.Crew bracelet – 40% off // Ettika Crystal Chandelier Earrings

I feel like you see the dress coming before you see me, and it has more of a fun festive aura about it that seems more appropriate for a New Year’s Eve party than a corporate black tie optional affair.

As an aside, I do not know why I look so awkward in these pictures! (All of them, except maybe the first one.) Shooting inside the house is weird. I can’t move around like I do when we’re outside, and I feel like I always look stiff and awkward, when in reality, I feel quite comfortable in this dress.

It’s also so easy to just slip on and go… although, now that I figured out how to arrange the satin foldover detail on the one-shoulder dress, it’s pretty easy too.

I kept on that gorgeous square-shaped crystal tennis bracelet with this dress, but I decided a black bag would look better than the gold, so I grabbed this pleated clutch about halfway through our photo shoot.

It has a gold chain that tucks neatly inside, but I will definitely use it at the event when I want to be hands-free

I went back to the Ettika crystal earrings for this one because the dress is such a statement on its own. I feel like these complement the dress without competing with it.

And I really should have taken this outside and photographed it with the black faux fur jacket I would wear with it. I think it would look so good together.

Here’s the dress with the gold baguette bag, but I feel like the black looks so much better. And I love the matte gold sandals look with this dress.

In fact, it is because I pulled them out to wear with this dress that I even bothered to try them with the two black dresses. I had ordered other options for those, but in the end, I think I’ll wear these no matter which dress I choose.

They coordinate perfectly with that gold baguette bag, if I end up wearing one of the black dresses, and they also look great with this dress and the black pleated clutch.

So yeah, after all that, I am still not sure which dress I want to wear. I’m leaning towards the one-shoulder because I feel like it might be more appropriate for the event, and it best exudes the overall vibe I want to present.

At the end of the day, they are both good options, and it really doesn’t matter which I chose, so I might just bring both and see which one feels most comfortable to me once I get there.

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photos: Alison Cornell

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188 Responses

  1. The off the shoulder dress is the one. From following you it strikes me as the most you. Keep the strapless and wear it somewhere less formal because it looks great on you. To me the sequins look like like you are trying to be festive.

    1. Definitely the Eliza J one-shoulder velvet dress!! You are beaming in that dress!! It is sexy, yet classy. Absolutely beautiful on you, Jo-Lynne! My husband knows I follow you, so I showed him all three and asked his fav. He immediately chose the one-shoulder velvet! Have a lovely time at the gala in Chicago!

    2. The off the shoulder dress is IT!!!!! Love it styled with the long earrings and tennis bracelet. You look like “you” if you know what I mean. It’s very appropriate for Black Tie optional.

      Amazing to see three outfits fully accessorized in photos BTW. Hope we get to see a pic of you two at the event!!!!

  2. You look amazing in all three of them, but my hands-down favorite is the one-shoulder. Very elegant. Simple. Gorgeous. I agree with you on the last one – it’s beautiful, but maybe a bit too much for black-tie optional.

  3. All are gorgeous! I agree, now that you’ve said it, that the gold patterned dress looks NYE-ish. The one-shoulder is stunning, and definitely looks like it fits into a black-tie-optional event. But really, any of them are a winner.

  4. I love the velvet on you….there is something about Velvet that just exudes class and style.
    THe gold is also pretty but the velvet gives you more shape. The strapless it just seems like you have to try too hard to make it work, honestly, I feel its over accessorized which then takes away the simplicity of the dress.
    I love just the earrings and bracelet with the velvet one, No necklace required.

    Have you tried putting your hair up? It might just add that bit of formality and show off your earrings even more.

    Have a great weekend.

  5. I chimed in for the Vince dress in your second round of dresses but now Im going with the one shoulder.
    I still think the Vince dress is perfect for you and that you can keep it for another time but the black one shoulder looks more fitting and elegant for this paricular occassion.

    You will stand out in the Vince dress and possibly blend in with the black dress.
    Sometimes I actually want to blend in and am more comforable with that …
    so something to ask yourself as well. You do look great in both!!
    PS Ive been waiting for this post lol

  6. All gorgeous but the one shoulder is the one. First one is nice but you don’t seem comfortable with it. The last one is amazing too but I think looks more New Year’s Eve party than pre-holidays. Enjoy!

    1. I agree with everyone else.. the velvet off the shoulder is THE ONE! They all look great but that one looks like it’s more appropriate for the event! Have a great time!

  7. We (my husband and I haha!) love the middle option (one shoulder). You look amazing in it, and it seems perfect for the event.

  8. I love the one-shoulder dress! That one seems to be the perfect combination of “appropriate for the event” and “true to your personal style”!!

  9. I love All 3 dresses on you !! I agree with the some of the comments, but hands down the Black off shoulder is Absolutely gorgeous on you !!

  10. I love All 3 dresses on you !! I agree with the some of the comments, but hands down the Black off shoulder is Absolutely gorgeous on you !!

  11. 3 solid choices but the 1 shoulder is my pick. Though if it were me, I’d take both that and the sequin dress and have a game time decision on how I’m feeling and then take into consideration how much walking I’ll need to do. Are you staying at the hotel where the event is? Or do you have to walk to get there or if it’s cold just Uber/Lyft. I hope you have a great trip and enjoy Chicago, it’s beautiful this time of year even if it is windy and cold. I was just there at Thanksgiving and just to warn you they turn the Christmas tree off at Millenium park at 11 CST, we missed it by 2 minutes our first ight since we were still on EST.

  12. I agree that the off the shoulder dress knocks it out of the park. Have a fun evening and know that everyone will adore you for what’s inside

  13. You look beautiful in all of them, but I vote for the one shoulder dress. It is perfect for the event and you look stunning!

  14. The one shoulder for sure…it’s stunning! All three are beautiful but I think you’ll be happier and more comfortable with the one shoulder. Enjoy the party.

  15. I’ve been dying to ask the venue for the event and range of employee ages… Hotel ballroom? Milleniels to Gen Xers? Go with the short blingy sheath, super fun. Smaller resturant? Gen Xer’s and Boomers? I would go with the velvet one shoulder 🙂

    1. Great consideration, Amy! I agree that the short blingy dress is more youthful and fun, would be perfect with a younger crowd. The off shoulder black dress is definitely more “mature” and elegant. Either way, Jo-Lynne should certainly keep both dresses for other events in the future. I really love that Vince Camuto dress!

  16. This series has been so fun to follow! Thank you! One shoulder dress is my choice too, elegant and sophisticated. You look beautiful and can pull off all of them, but you are right, for this event, it’s the best!💜

  17. The one shoulder dress is stunning on you. Classic and elegant with a twist. I also love the embellished Vince dress, it’s so fun. Take it along just in case. But, keep it regardless. My husband has had company parties in the past and I know how deciding what to wear becomes an all consuming task. Have fun!

  18. All look beautiful on you! My favorite is the strapless dress. It is just so understatedly elegant and classic.

  19. The Eliza J one shoulder dress is the winner to me, just beautiful and classy with the bracelet and longer earrings and bag. It looks comfortable too. The strapless is also so pretty on you but it seems like a more sheer wrap that is not as wide that would show through that the dress is strapless would be an option for another event. The black and gold is gorgeous too but maybe more appropriate for another event.
    I know you will enjoy your trip and event and will look beautiful as always!

  20. As someone who’s attended umpteen urban corporate holiday dinners in a previous life (NYC not Chicago, but close enough), it’s definitely one of the first two. I voted for the black strapless last time and I’d still choose that one if it were me, but it’s you, so I vote for the one-shoulder. I think you’re clearly more comfortable in that one and it still looks great for this type of event. The last one IMO doesn’t quite hit the right notes for this kind of thing even though it looks great on you.

  21. A great ride along on the dress journey. I’ve pretty much been team strapless, well accessorized, all along. The previous size of the one shoulder one threw me off and I questioned if it was an option at all given the fit. While I think the sparkly one is “okay” I’m not loving it visually across your shoulders. Maybe it’s too much coverage? I feel like there’s a horizontal line that’s creating some width there and it’s messing with me. The one shoulder in the size you’re showing here today is truly lovely. I know the dress is really important but in all of these any little not perfect detail will be unnoticeable with your fabulous smile. Have an absolutely luxurious time!

  22. Definetly the one shoulder one. I love how you look in it, accessorized it and it seems more appropriate for the occasion. I think the length is perfect; makes it more formal. I love the short gold and black one, as it was my first choice at first, but I think the one shoulder is better. I’d keep the gold and black one for another event. Don’t even bother taking it to see how you feel. Just make it simple and choose the one shoulder and go. lol. You look so pretty in it. Love the sandals. Someone mentioned wearing your hair up. I’d wear it down. It’s so pretty. By the way. I hope you show us what Paul ends up wearing. Be sure and get a photo. Have a great time. Are you driving or flying?

  23. Oh, the Eliza J one shoulder is the winner!! Save the other for NYE!
    You look stunning in all 3, though!
    Have a safe trip and enjoy the party!!! 🎄

  24. One shoulder for sure. Matches your style and the event and I imagine you feeling that feeling of peace at the event when you feel happy with what you’re wearing with a glass of wine in hand. Also buy the festive one and wear it for nye or a fancy holiday dinner out. Keep the strapless one in mind if you ever need a simple strapless

  25. Middle dress for the win. It clearly makes you the happiest. You look great but your attitude gives the edge at events like these. Have fun!

  26. I definitely like the second! Although they all look good! I’d be worried about meeting the third dress on someone else 😂!
    I have no doubt you’ll pick the one that feels right the day of and great idea to take all the options. I’ve done that to incase I change my mind 😉
    Have fun!!!

  27. Oh wow! Those two black dresses are great. The fur with first one looks so rich. You can walk in the room with confidence!
    Your hair has gotten so long, looks great!

  28. I love them all but in my humble opinion the one shoulder dress is the perfect combination of elegance and simplicity. It’s very flattering. I think you could be comfortable and confident snd not self conscious. But you wear what makes you feel the best! The best thing you can wear is a smile!

  29. You look amazing in all of the options, but I think the one shoulder is modern, flattering and just the right look for that event. Cheers!

  30. All lovely looks but the Eliza J one shoulder seems to check all the boxes! The strapless seems too plain and the cap sleeve one does look more suited for a New Year’s Eve party, as you stated.

  31. The satin wrap off the shoulder dress- it’s you. Classic, elegant and not trying too hard. The cap sleeve dress is very pretty on you as well but I agree it’s more NYE appropriate. Enjoy the evening!

  32. Go with the one shoulder, makes your figure look great. Runner up the last one. I too follow Susie Wright and feel she is “my style” but that black strapless is an evening style you would wear here in California or on West coast. Love your accessories. One suggestion if wearing one shoulder, you may want to wear your hair a little up or back a little…but leave curls. 😉 have fun at the event. You’ll probably be best dressed there.

    1. I was thinking of pulling one side back with a pretty clip but I tried it at home and it didn’t quite work. I’m terrible with hair. I hate to take the time to go to a drybar but that’s what I’d have to do if I wear it up in any way.

  33. You look stunning in all three but the one shoulder with those earrings wow! I hope you are keeping the Vince Camuto for another event. It looks amazing on you too. Have fun.

  34. I love all three! For your event, I say go with the one shoulder the way you’ve styled it. Re: the strapless, nice but get a different bracelet as you stated and since you’re already fussing over a wrap — go with the one shoulder dress. It looks timeless and elegant and you look like you (only fancy!). The metallic dress is great! But it does look like NYE to me as well not black tie optional. I think I would also like the black clutch and some black pumps better. The photo with the black clutch seemed to ground the look whereas the gold is too much with the dress. For what its worth — just my opinion. You look great in all of them – enjoy your event whatever you wear!!

  35. Hi JoLynne—I like both dress number 2 and 3. Dress number 1 is a definite no—if you feel like you have to cover up the shoulders, what’s the purpose of a strapless dress? Just wondering if you’ve decided on what outerwear you’d be wearing with dress 2 or 3 or does the event take place in the hotel where you’d be staying? If so, great. Your accessories you’ve chosen for dress 2 and 3 are perfect.

    For the future, have you ever checked out Whiting and Davis handbags? The best selection is from their own site. They’ve been around for years. They have lovely handbags.

    1. Oh yes. Outerwear. Definitely a black faux fur crop jacket if I were to go with #3. I’m still debating with #2, which I do believe is my final choice. I need to see how my jackets fit over it. I could possibly do that grey faux fur capelet. Or the black faux fur jacket. Or just a long black wool coat? Is the boucle one dressy enough? I do need something. We will take a Lyft from hotel to party venue.

      1. If you have time, can you take pictures with those outerwear choices with dress #2? I’m not in love with the gray faux capelet. I can’t place my finger on it—maybe the color doesn’t look as elegant or compliments your coloring and it seems to make your shoulders look wider (although that may be the angle of the picture). I don’t remember the length of your boucle coat. Will the dress stick out from the bottom? If so, I would go with a shorter jacket, unless you have a dressy black wool coat that would cover the length of the dress. Such dilemmas us women have to go through. It takes a lot to coordinate a full outfit.

      2. I believe I put my finger on it. The gray cape looks mousey to me. It reminds me of the older color furs that people wore back in the 50-60s. Black fur or faux fur would look more updated.

  36. Thank you for sharing your thought process as you make your dress selection. You’re so good at articulating important factors to consider!

    I recommend the ones shoulder dress; super flattering, stylish & modern!

  37. Such a fun ride with the cocktail party dresses, Jo-Lynne! Thanks so much for engaging us in your journey to find the perfect dress. I agree with most comments and choose the second dress, off the shoulder. The dress looks absolutely gorgeous on you! I also wonder what Paul will be wearing. Would love to see a few “pre” photos of the two of you together. Maybe that will also help you make a final decision. And, I too agree – make a decision before leaving on your trip. It will help you mentally prepare for the event. Whatever you decide, you will look gorgeous! Have fun!!

  38. My vote is for the one shoulder. It seems more appropriate for the event you describe. But I wonder if a different shoe choice would be better. I agree that the gold and black shorter dress looks great. Shoes, bag and all make it a great outfit. But it does not seem appropriate for the event. It seems more attention grabbing. Maybe not the look you want for this event.

    1. I agree with both points. I’ve been rethinking the shoes with the black dress. I may need to suck it up and wear the higher black Stuart Weitzman heels. The problem is, they have silver embellishment and all my accessories have gold. 🤪

      1. April may have a point, I was wondering about black shoes or sandals but figured you went with the gold because less of a contrast from your skin tone and not breaking up the long line especially since your dress is a little longer than you usually wear them.
        If the SW shoes work with the dress, I would purchase different earrings and bracelet, etc. with silver tone to blend better. Have you ever checked out the jewelry from Swarovski or Nadri? They both have beautiful pieces. I would carry a clutch which may be a little more cumbersome but I feel it looks for elegant.

        1. I didn’t even think about wearing the gold shoes until I put on the metallic dress, and they seem to work well with that one, but they’re a little more casual (which is in keeping with that dress) than I really want for this event.

          I ended up wearing them with all 3 b/c I like how they pair with that Loeffler Randall crystal baguette bag. I like that they are matte, and it is sparkly. The other shoes (the sparkly gold ones) seem too matchy, and that low heel and the cross-cross straps don’t seem to play as well with the longer skirt hem, but these don’t seem quite right either.

  39. Looks like overwhelming votes for the one shoulder. I really do prefer the strapless. That first pic of you outside in that dress and the wrap, so modern and current, much more than the velvet, in my opinion. But I get not wanting to fuss with a wrap. You will look fabulous in whichever dress you wear. Have fun!

  40. The one-shoulder for sure! It’s gorgeous, looks great on you, it’s very appropriate for a black tie event and the accessories are perfect. But keep the black and gold mini dress–it would be perfect for NYE! Then you can pull it out of the closet and when people compliment you say “this old thing?”

  41. #2 is the winner in my opinion. #3 is lovely but perhaps not quite formal enough for black tie optional. You will look lovely no matter which one you choose, so go with the one that makes you feel fabulous.

  42. I’m leaning on the one shoulder for this event. All 3 are fabulous! What is Paul wearing? Sometimes it helps to see you both side to side? The one shoulder with those amazing earrings have just the right amount of holiday party special look! Although I did favor the strapless, after seeing the wrap issues, I changed my mind.

  43. You look absolutely stunning in the one shoulder dress with the velvet! Classy and striking for such an occasion!

  44. The first dress with fur topper is so great. It feels like something Jennifer Aniston would wear. Modern, beautiful, elegant. That said, they are all truly beautiful and you have to wear the one that you feel is “the one”! Have fun!

    1. You did NOT just play the Jennifer Aniston card! Now you have me second guessing, lol. She is my style icon. I felt like the fur capelet might be aging. And the accessories didn’t quite come together but I could always shop in Chicago, I guess! I’m sure Paul would looooove that. 😂

      1. Haha! I love Jennifer Aniston’s style too and that comment would definitely make me keep it! I’d still wear the velvet for this event (seems a little dressier for some reason). But I’m sure you’d find an occasion to wear the strapless. Also if you wear it in the summer, you wouldn’t have to fuss with a wrap or jacket.

  45. all things considered (as you laid out), I vote for the one shoulder, velvet/satin combo. the metallic dress is fabulous but I agree it’s more NYE than formal company event.

  46. Coming to you here from Sunny Chicago! Third dress ALL THE WAY. It’s fun, festive and looks great on you! Definitely not too New Years Eve. Enjoy our glorious city this weekend!!!

  47. I definitely vote for the Eliza J! It just seems to hit the right notes for this specific event. But they all look great, I’d prob be tempted to buy all 3. You never know when you’ll need a black and gold sequined dress, right?! Wear whatever you feel most comfortable and confident in. And have fun!! Did you say y’all are going to Chicago for this event? Hope you can turn it into a quick little couples getaway trip!

  48. I really like them all, but the heavily beaded one the least.
    The one shoulder is the most striking and it really does look lovely. I also love the longer earrings. Would you wear the black faux fur coat with that one? or the shruggish thing? I think they’d both look nice.
    Meanwhile, your husband just has to put on a nice suit and he’ll look like a million bucks. It isn’t fair! But then, they also don’t get to do the sparkles.
    Have fun!

  49. I absolutely love the 2nd dress … nothing to fuss with and you can enjoy the evening and being at a beautiful party with Paul ❤️

    Have fun !!

  50. Though my first vote was for the Vince black and gold, I’m going with the velvet off shoulder with simple accessories. It’s elegant and sophisticated, while still feeling modern. I love your choice of gold shoes and bag, as opposed to black, which seems so expected and ordinary. The length, especially with the demure side slit, will be appropriate for black tie, yet still look youthful and festive. The Vince black and gold is so so cute, but definitely seems better suited to NYE or other less formal event.

    I’m curious if this is the first Christmas party like this for Paul’s Company you’ll be attending (I’ve only followed you since 2020, when corporate events like this were curtailed) and what the demographics of the attendees will be (age/generation, female S/O of an employee vs female employee…). Can’t wait for the post event recap!!

  51. Love the one shoulder dress for this occasion! It’s perfect! The other two are not-enough and too-much. Hope you have a wonderful time!

  52. I absolutely love all three dresses on you!!
    Also agree that the one shoulder dress seems to be what you feel most comfortable in. However, it will most likely be what every other woman will be wearing. Do you want to blend in or stand out? For me, my pick would be the last dress. I would want something different than everyone else. Just a different take.

  53. They all look beautiful. I like the first one with the faux fur wrap, the second one as a stand alone, and I think you could make the third one look more formal and less playful if you wore a black sling back, high healed, pump and a black faux fur jacket or wrap. Then for New Year’s you could drop the wrap and wear with the gold sandals.

  54. Definitely the one shoulder dress for the event you are describing. You definitely rock it! The sequined one for NYE.

  55. I very seldom comment on your posts but I have to tell you that the one shoulder dress is stunning on you and YOU just have to pick that one. You will not be sorry having this dress in your closet. Enjoy your party.

  56. I love both dresses! I would take both and decide depending on my mood. You are stunning! Your accessories are classic and beautiful.

  57. My 19 year old son happened to be in the room with me while I was reading this post, and I asked him which one he liked best. He immediately said the second one, the velvet with one shoulder. So there you go! 🙂

  58. Jolynne,

    I think they all are good contenders, but I love the black one shoulder dress. It looks very elegan and makes a statement. The last dress reminds me of something that could be worn to a wedding or as you said NYE.

    HAVE FUN!

  59. One shoulder dress for sure! Can you take a link out of that tennis bracelet so it fits better? Not tight but just not quite so loose?

  60. I also love the off the shoulder dress! You look great in all three but this one seems perfect for your occasion. Hope you both enjoy the event and have a wonderful time. Merry Christmas and Happy New Year to you and your family.

  61. Gorgeous dresses! I still pick #2 for me! So elegant and you wear it beautifully! Whatever you pick you have a great selection.

  62. I know most people love the one shoulder option and I do too. However what will you wear over it to stay warm on your way there or while you are there if it is freezing?

  63. I don’t like the first one. It seems to do strange things at the bust line, seems less formal, and not as classy as the other two.

    My favourite one is the off shoulder one. It hits all the points – fit, comfort, style, appropriate for black tie, and figure flattering. And, those earrings are stunning! Love the heels and the baguette bag, too. You look very elegant in this one.

  64. Dress number 2 looks incredible on you! The longer length looks more formal and the silhouette is perfect. You’ll look beautiful no matter which but that’s my pick! Such a treat to get dressed up and attend a party in another city! Have a blast!

  65. I think you look great in all of them but for how you described the event I would vote for the second dress. Love how you styled it. So classy!

  66. The dresses are all lovely, but I like the black on shoulder fold over the best. It’s festive, shows your figure & is so pretty. But I’m sure whatever you were you’ll look fabulous!! Have an incredible evening!

  67. The off the shoulder velvet looks great on you and probably will feel better wearing that to the event vs the gold print dress. Have fu and enjoy, looks great on you.

  68. I thought you were a little nervous about the bird. I love the 2nd and 3rd look on you. The first one looks nice but not as nice as the other 2.

  69. You look gorgeous in all three of these! For this event, I think you should wear #2 exactly as you have accessorized with the long earrings, bracelet and gold handbag and shoes. I feel like the gold bag and sandals give the outfit the modern edge you want.

  70. I love the one shoulder velvet sheath. Love it with the long earrings and bracelet. The epitome of “effortless elegance.”

  71. The black off the shoulder one looks perfect on you! It is classy and elegant for a black tie event. You look great in all of the dresses but you want to enjoy the party and not have to fuss with something to cover your shoulders. The third dress looks good but more like New Years dress to me.

  72. You look amazing in the one shoulder, it looks very classy yet still young. I think for a work event it’s the one!

  73. I vote for the one shoulder dress! It looks super classy and chic on you, though I do really like the shorter metallic sequins one as a runner up! Also, it may just be me, but I think the strapless dress would look better if it weren’t so narrow at the bottom.

  74. Ok the one shoulder is beautiful and fits the bill perfectly. But that third dress stands out! You still got the leggs!

  75. The Eliza J velvet dress!! Looks beautiful. Love the jewelry choices. The satin band IS a beautiful “necklace” so no other is needed!

  76. The one shoulder looks amazing, great choice!! If I may offer a suggestion to raise the satin shoulder up a *little* bit more, give it a more interesting angle? I would like to see it personally 😊 it looks a tiny bit constricting on the shoulder to me…could just be me though.
    Also. I say this next tip with lots of love, to use a hand moisturizing glove/wrap treatment right before the event, it’s so dry out, especially in Chicago, and the pictures will look all the better for it 💓

  77. Forgot to mention, your hair looks so pretty curled like this! I know others have suggested an updo but I’d definitely wear it down and curled like this. If you choose the one shoulder dress, you could pin a couple strands behind your ear on the strap side; the asymmetrical hair would echo the dress.

      1. I’m terrible with hair but I’ve done that style a couple times. It helps to part it a bit off center so you don’t have as much bulk on that side. But I do struggle with anything that involves bobby pins, especially if I’m trying to get them not to show! A dry bar could be a fun way to relax before the party.

  78. I really like the second and third dresses. I’m not crazy about the first one. Given what you’ve said about the event, I vote for the one shoulder dress. I like your idea of taking two with you and deciding there. You look very nice in them. Have fun.

  79. I agree with you – the black velvet/satin one shoulder dress seems more in line with a more formal event and the shorter metallic dress seems more of a party dress – but I do love the way it looks on you!

    But either one will be fabalous!

    Hope y’all have a safe trip and a wonderful time!

  80. Hello Merry Christmas!!
    Love all … my favorite the last
    Vince so party ready!
    I live in Chicago … cold wet for Saturday..
    Your new short fur coat perfect!

  81. I vote for the one shoulder dress. The strapless one is cute with the fur thingy too. But I think you’ll be more comfortable with the one shoulder one. I don’t think I like the gold one as much anymore. I like your hair too. You’ll look beautiful. Go with what makes you comfortable.

  82. Of course they are all great, as you wouldn’t narrow it down to options that aren’t. But my favorite is by far the first option. It’s such a modern, on-trend length that is flattering and chic. I also love that it’s strapless. It is definitely not a plain gown. I haven’t worn anything strapless in years.

  83. I like the black Eliza J dress on you best. The metallic dress looks great on you but it may be a little short for black tie optional? It seems like the first dress was too fussy (as in how to accessorize) for you but you look beautiful in it and it looks appropriate for the event.

  84. One shoulder one definitely! The first one makes you look too heavy with the wrap. I like the print dress second.

  85. fab-uuuu-looks!!!!! Love the first 2!
    I like #3. It’s definitely a safe choice.
    You look great & confident showing some skin,,not to mention 🔥. I vote you step out of your comfort zone, go with 1 or 2.
    Beautiful lady!

  86. You can’t go wrong with any of the three. I like the Eliza one the best on you u.You look stunning!
    There is nothing wrong with a dress or outfit that you see before the person. Perhaps there are times when this what we want!!! I like the Camuto also..

  87. Number 3: The black and gold is the best and looks the best on you. Everything about this look fits together perfectly. Its feminine and very flattering and looks very comfortable and unfussy.
    The first two are not flattering, especially the first one. The fur stole and the shimmery wrap and the purse look out of form….nothing seems to go together. It’s also matronly and not in a good way!
    The second black dress is better but again, just okay and this looks has been seen before over and over.

    Choose #3 and have a great time!

  88. You look lovely in all of them, but I definitely prefer the black one-shoulder dress. It just looks more elegant and is very figure flattering.

  89. You look fabulous in all three dresses, but I think the one shoulder dress strikes just the right balance for this event and how you’d like to feel that evening.

    I think the strapless dress might cause you to feel just slightly less than 100 percent comfortable that evening… but it would be fabulous for another event.

  90. I vote for #1, or #2. These both allow the jewelry, and YOU, to shine! You look stunning, either one. #3 looks more like New Year’s Eve to me.

  91. My vote is for the black one shoulder dress. You look amazing in all, but this one is the perfect mix of elegant and current.

  92. My favorite for you for this event is the velvet one shoulder. You look stunning!
    But the black/gold Vince dress looks awesome now since you found the correct size. It fits you much better in these photos.

  93. You look stylish in all three dresses but that one shoulder dress steals the show. If you feel comfortable, then it’s much easier to enjoy your evening.

  94. The velvet off the shoulder looks wonderful on you – very elegant and modern. Your makeup looks great as well. Can you share what lipstick brand and color you are wearing?
    Have a wonderful evening!

  95. Please wear the one shoulder dress! Modern and classic especially with black shoes! The strapless is fun for another occasion!

  96. I love all three looks! It’s really hard to decide, but ultimately from what you’ve said, since all three fit well, are comfortable and accessorize beautifully, I think it comes down to the one that exudes the vibe you want to present at this event. So, my vote is for the one-shoulder dress!

  97. Love these choices. You look more comfortable in these dresses than the ones you were trying to make work. I don’t think you can go wrong with any of the 3 above! Have fun!

  98. While my top pick is the Eliza J off shoulder dress, I know that you will look fabulous in whichever dress you wear, and that Paul will be so proud to have you by his side. I hope that y’all have smooth flights nd an enjoyable weekend. You know that we want to see a picture of the two of you.

  99. Love the last two and I agree with you that the one shoulder is more event appropriate. The gold and black is a definite winner, though so youthful and flattering and gorgeous – great New Year’s dress.!

  100. I absolutely love the one shoulder Eliza J dress with the statement earrings, no necklace, and the bracelet. Also the gold shoes and purse are perfect! I think the one shoulder is more updated than the strapless one, and the 3rd one seems a lot more casual than the one shoulder. Like you said, maybe for a NYE party?

  101. I know everyone is gaga over the one-shoulder, but I prefer the black tube dress with fur stole. I think it’s different, but not crazy out there for your style, and it’s current and sexy on you, in a classy. way.

  102. That one shoulder dress doesn’t need another vote but it has mine anyway! Perfect in fit and for the event.
    I bought the J Crew necklace for myself and one (plus bracelet) for daughter-in-law. They are beautiful pieces.
    I wouldn’t bother with an updo hairstyle. The dress is dramatic enough. Also for some reason I think hair worn down looks more youthful and modern.

  103. I love the 2nd dress (off shoulder) – you look extremely elegant and put together, especially with the earrings! I agree the 3rd option is probably more suited for a NYE party, and frankly, i’m not crazy about option #1, especially not with either of the wraps. Whatever you choose, I’m sure you will look beautiful and have a great time!

  104. You look beautiful in all three – I like the 3rd dress best. The one shoulder is elegant and would really pop with some red shoes.

  105. The off the shoulder dress has my vote. Love the long earrings and the tennis bracelet. I wouldn’t wear the fur wrap, it looked like something I wore in middle school. You looked simply elegant and very classy,

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