Try-On Haul: Holiday Cocktail Dresses

Okay, friends! The long-promised and much-awaited holiday dress try-on haul is finally here! This post is going up super late today, but if you’re anything like me, you have events that are looming, and time is closing in, so I didn’t want until next week to share.

I have an event I’m shopping for, so this post is as much a personal search for the perfect cocktail dress as it is a resource for you. In fact, I’d love to get your opinion on which dress I should choose, if any. I’m conflicted, and even my husband and daughter are kind of wishy-washy on which one they think is best for the occasion.

I’ve decided that shopping for cocktail dresses when you’re in your 50s is a unique challenge. Suddenly, the sheath dresses that have been my go-to all my adult life seem to look somewhat matronly on me now, but more trendy styles feel too youthful. It’s a conundrum!

The event is my husband’s company holiday party, and the dress code is cocktail attire/black tie optional. I could wear a floor-length gown if I wanted to, but I’ve been ordering shorter cocktail dresses because they seem more comfortable to me.

Anyway, this intro is long enough so let’s dive on in! I can explain more as I show the dresses.

Holiday Cocktail Dress Try-On Haul

Please, note, these dresses are NOT styled how I would wear them. I did try to wear shoes that somewhat match the style and formality of each dress, but none are ideal. When I decide on a dress for my event, I will shop for the shoes, jacket, bag, and jewelry I need to complete the outfit to my satisfaction

SIZING NOTES: I’m 5’5″ and I usually wear a small in tops and dresses, a 29 in jeans, and a size 8 shoe. Gifted items are indicated by c/o; everything else I purchased myself.

Steve Madden Long Sleeve Sequin Dress

at Nordstrom (M) // Talbots slingbacks c/o (8)

I don’t think I ever would have noticed this one online, but one of YOU reached out to me about styling ideas, and I thought it looked like it was worth a try.

But alas, it’s not quite right for me. I don’t care for the length on me, or the large and in charge shoulder pads. I have built-in shoulder pads, thanks to my boxy shoulders, so they are the last thing I want inside my dress.

VERDICT: This dress went right back, but if you like a shift style, and you need the extra structure provided by the shoulder pads, this might be a great option.

Pisarro Nights Beaded V-Neck Cocktail Dress

at Nordstrom (6) // Marc Fisher pumps (8)

This dress is very much my style and follows my body type “rules” or best-practices. I don’t really like the idea of rules when it comes to fashion, but I do know that I look best in v-necklines, structured silhouettes, and traditional set-in sleeves. This is also a good color on me, and it looks festive.

So why do I feel like the whole look is dated? Maybe it’s the length, or the fabric and the design of the beading?

VERDICT: I can’t put my finger on exactly why, but this dress doesn’t make me excited to wear it. I just feel like I’ve seen it a hundred times before, even though I have never worn one quite like it.

Eliza J Blouson Sleeve Sequin Cocktail Dress

at Nordstrom (8) // Talbots slingbacks c/o (8)

I’m not sure why I ordered this because I detest keyhole necklines. Again, I can’t exactly explain why, but the always seem old-fashioned and matronly to me. Otherwise, I love the silver sequins and the 39″ length.

The blouson sleeves are pretty too, and they give it a more modern vibe, but they really aren’t my personal favorite. I feel like they overwhelm me and I’d prefer to showcase my slender arms, and the shoulder pads seem to take over with this one, as well.

VERDICT: I returned this one. I feel like I can do better.

Eliza J Blouson Sleeve Sequin Cocktail Dress

at Bloomingdale’s (8) // Talbots slingbacks c/o (8)

And yeah, no. I think you can tell by the look on my face how I felt about this one. Too low-cut, too much shoulder pad, blouson sleeves again, and I was beginning to think at that point that I didn’t even want to wear sequins or a beaded dress at all.

VERDICT: Returned it.

Sam Edelman Drape Neck Stretch Velvet Cocktail Dress

at Nordstrom (8) // Talbots slingbacks c/o (8)

I love velvet for the holidays, so I was excited to try this cowl neck number, but I really don’t care for that asymmetrical hemline. I would also prefer sleeves.

VERDICT: Returning.

Alex Evenings Side Ruched Velvet Cocktail Dress

30% off at Nordstrom (10) // old Stuart Weitzman heels

Another velvet option, this one with sleeves, and I love this burgundy color. I can see this is flattering, but I wasn’t sure about the ruching and draping and that big embellishment on the side.

It didn’t help that my daughter told me it looks like something that would be on one of her American Girl dolls, or something a child would wear to church at Christmastime.

But it’s warm and comfortable and flattering and a great color, so… I dunno. Why does that dreaded M-word keep coming to mind!?!

VERDICT: I’m holding onto this one; it may be a contender. As an aside, also love it with these shoes, but I don’t think I can walk in these 4″ heels all night. I wore them to a wedding a few year ago, and my feet were numb for days. I saved them because I love them, but I’ll be looking for something with a lower heel.

Vince Camuto Jacquard Fit & Flare Dress

at Nordstrom (8) // Marc Fisher pumps (8)

Okay, so this is a TOTALLY different style for me, obviously, but I was starting to feel like everything I was trying looked the same, so when I saw Cyndi style this last week, I thought I should give it a shot. It’s free to try, after all!

First of all, this is a size too small. It looks fine from the front, but I couldn’t get it zipped up past my waist. But that aside, I just feel like the full skirt looks really juvenile on me. Some women can pull it off, but it’s definitely not my vibe.

I do like the metallic jacquard print, though, even though my family assuredly did not.

VERDICT: Returning, but I would recommend trying it if you like it. It’s a pretty dress, and the metallic jacquard print is modern and fun.

Adrianna Papell Jacquard Sheath Dress

at Nordstrom (10) // old Stuart Weitzman heels

This is another jacquard print, and I love the shimmering metallic branches on the navy background, but the fit is off. I’m short-waisted, and it really needs to be taken up in the shoulders to fit right. It’s cut way too low under the arms, and the ruching across the chest region poofs out in a funny way.

I suppose it could be altered, but my husband was not a fan of the fabric, and since this is his work event, he gets veto power. Plus, I don’t feel like dealing with alterations if I can find one that fits off the rack.

VERDICT: Once again, returning, but I like the idea of this, and I would recommend trying it if you like it.

Halogen Jumpsuit

at Nordstrom (S) // Marc Fisher pumps (8)

Obviously, not a dress, but this metallic jumpsuit is really fun. It just didn’t fit me quite right. I have a hard time with jumpsuits because I have a high waist but a long torso. Let’s just say, it wasn’t very comfortable. I also don’t fee like it flatters me the way some of the dresses do.

VERDICT: Returning, but definitely try it if you like the idea. I think this could be really cute on someone.

Alex Evenings Embellished Ruched Sheath Cocktail Dress

at Amazon // at Nordstrom // old Stuart Weitzman heels

Then yesterday, this red embellished ruched sheath arrived. I found this one at Nordstrom, but the red was out of stock in my size, so I tracked it down and ordered it from Amazon. The other colors definitely have a Mother of the Groom vibe, but the red feels very holiday to me.

It has a similar design to the Alex Evenings velvet side ruched dress above, but I love the shape of the neckline on this one, and the fact that there isn’t as much fabric draping around the hip area.

This seems a little more streamlined and sophisticated, although I’m still unsure about the big embellishment on the side.

I’m wearing the size 8, above, but it was a little tight across the rear, so I tried on the 10 and added sheer black hose and closed toe shoes. (I actually tried it this way after I tried on the next dress, but for the sake of organization, I will include these photos here.)

The size 10 feels better on, but I feel like the 8 looks better. Am I imagining things?

Also, I’m not sure I like the black hose with it. It will definitely limit my shoe choices, but I also don’t know that I want to go without any leg coverage in December in Chicago. I might try a nude fishnet, if I decide to go with this dress.

VERDICT: Holding onto this one for now… it’s a contender, for sure!

BlankNYC Shawl Collar Faux Fur Jacket

at Nordstrom (S) // dress (8) // old Weitzman heels

I also ordered this jacket, even though I have the Gap Factory one. I thought the shawl collar might look dressier, but I think it overwhelms me.

Also, the fabric on this dress isn’t warm at all, so I might just wear my black boucle wool coat and check it.

Vince Camuto Sequin Long Sleeve Cocktail Dress

at Nordstrom

This dress also came in yesterday, and I almost didn’t try it on at all because I was so over trying on dresses, and I thought for sure I would feel like the Grandmother of the Groom with the center ruched design, but it actually has some potential. I think the shorter length saves it.

I just wish it was not quite so low-cut in the neckline. Plus, the shoulder pads are a total deal breaker. Just the same, I wore it downstairs to get some feedback from my husband and daughter.

They both rather liked it, but agreed the shoulder pads were an issue. After taking pictures, it occurred to me that it might be too big, and I remembered that I had also ordered the size 8.

So I ran back up and changed into a different bra and swapped the 10 for the size 8. Of course, that made it even shorter, so I added black hose, but there was still the issue of the shoulder pads.

I was dying to see how it would look without them, so I verrrrry carefully cut them out. I just had to know if that would make the difference I was hoping for.

(I won’t return it to the store without them, but I can sell it if I decide not to wear it.)

So tell me what you think, now. I feel it’s a huge improvement.

If I keep any from this post, I feel like it comes down to this one or the red ruched sheath.

My husband and my daughter aren’t any help; they say both look good, but truth be told, I don’t think any of the three of us are super excited about either.

What say you?

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206 Responses

  1. I absolutely loved the shape of the red on you but also liked the material of the black – definitely both my favourites of your try on haul. Thanks for sharing your struggles as (to me) you look good in everything!!!

  2. I think you look lovely in the last two you picked but in my opinion I think you might be able to find something better. When I put a dress or something on I instantly feel this is the one. So ,do you feel that way about these two dresses? If you have time don’t settle just yet. But, if not ,go with what you feel the best in. You look great in both!

  3. The Vince Camuto is definitely better without the shoulder pads. I’d go with that one, or the beaded one that you weren’t sure about. I really liked the beaded one.

  4. I like the two that you’ve chosen but I also liked the Pisarro dress. Yes, you’ll need something on your legs in Chicago. Try the Pisarro dress with sheer black hose and black pumps. If that’s too dark, why not go with a sheer nude-to-you hose (nylons, not tights).
    As far as the other two choices. I like the black dress neckline better on you and it’s perfect with the sheer nylons and black pumps. I would try the red dress with sheer nude nylons and black or nude pumps. I don’t like the sheer black hose with the red dress. Too much contrast and breaks you up.
    Keep us posted and maybe try these options also and post more pictures.

      1. The Pissarro dress was very pretty, but unfortunately the pattern made two “boob bullseyes” across the chest 😳

    1. I agree about the black hose with red dress. I will wear dressier shoes if I decide on the black sequin dress. I can’t get excited about the Pisarro dress. I will keep you all posted!

  5. Being the same age, I relate to this so much!! (Except you have better legs, lol) Between the two of them – I like the red better (without the black hose)…but I honestly liked the green velvet with the cowl neck the best…if it had a straight hemline (that’s no help, I know!) 🙂

  6. Jo-Lynne,
    Like you I feel I look best in a sheath. I wore this dress to a black-tie optional event in the fall. It comes in lots of colors and is even on sale right now. It ran a little small in the waist for me-I sized up and had it taken in on top.

    1. Thanks, Beth. I have seen that and included it in roundups but it didn’t occur to me to order it. I think because I prefer not to wear a strapless bra. But on your recommendation, I just ordered a black one to try.

  7. I like the Pissarro dress on you. It fits perfectly and is elegant. The red dress is a winner! It shows off your figure perfectly, is elegant but a touch sexy too, I would wear nude hose and shoes with it. The black seems harsh.

      1. The red is my favorite on you…keep for backup. I’d do a black patterned tight*. If you did a nude fishnet with black shoes, it doesn’t feel elegant enough. *Plain black looks outdated. I don’t know if any of the dresses came from Bloomingdales but they seem to have a ton of dresses.

  8. If you have the time, I’d recommend keep looking. You are so cute and stylish neither of these dresses quite make it. I *really* like you in flares… what about black flares and a super sparkly top with impossible heals?! Maybe everything feels off because you don’t actually want to wear a dress this season? (I don’t so I’m projecting!)

  9. Between the last two, I vote for the black one. Very flattering now that you took the shoulder pads out, and looks more appropriate for a black tie optional event. I actually really like the brocade dress on you (the first one from Cyndi’s blog). Totally different but trendy and fun. Also idk if it’d be dressy enough for your event, or what the quality is like, but I saw a really pretty green velvet burnout dress at Kohls. Somehow the burnout pattern made it look elegant to me.

  10. I think the hands down winner is the Vince Camuto black sequin dress (once you took the shoulder pads out!). It looks terrific on you. Personal opinion, the red looks rather dated. Don’t go the safe route, go for the sequins. It looks like it was made for you!

  11. I think the red dress fits you better than the black sequined one. Go with nude hose and be very careful about your shoe choice. That might be what is killing the vibe. The black block heel is screaming funeral vibe/matronly. If this event is in Chicago, then it will be cold as heck. What about a trendy bootie or knee length boot? That would break up the vibe that you feel is matronly. Gen Z always wears booties or boots with their dresses. It would give you a more youthful vibe while keeping you warmer. You have gorgeous boots, so change it up with that. Also, try longer dangling earrings and maybe your hair up. If you chose the black dress, same thoughts. Careful with shoes and try booties/boots.

    1. I totally agree about the shoe choice, but I don’t think boots are the answer here. It’s a conservative industry. That said, I do want to look modern, so… yeah. I have some work to do! I have no intention of wearing those block heeled pumps. I just put them on to have shoes on, but they are not dressy enough.

  12. Black dress black hose…great. Red dress black hose, no. I also .iked the deep color velvet dress. If the side embellishment is a no go, perhaps you could replace it with something else.

  13. I really like your 2 contenders. I think after you took the shoulder pads out of that one it looks so much better. I did really like the burgandy velvet one too.

  14. Wow, thanks for the visual fashion education thru all these pictures, Jolynne! Even just the shoulder pads made such a difference, let alone the length of the dresses! So many times WE are not the best judge of what looks best on us AND our family members can be biased or just want the questions to stop! 🙂 Tee hee! We appreciate you!

  15. Jo-Lynne,
    I really like the black dress after you removed the shoulder pads. I think it would be comfortable and you could pair it with some cute shoes that won’t hurt your feet.
    The red is a close second.
    Thanks for answering about the Field Sneakers— already ordered!

  16. I really like the fit of the red dress on you. I also think the green dress is beautiful and might like that one best!

  17. Definatsly no shoulder pads! The black dress looks much better without them but the red is my favorite, especially for a work event.

  18. The last two are definitely my favorites on you. The neckline on the red seems rather high.Taking out the shoulder pads on the black was a huge improvement. I would go with the black, or keep looking for something more in keeping with your clean aesthetic.

  19. I actually like the Vince Camuto fit and flare dress or the burgundy velvet dress the best on you. But of the two choices at the end, I like the red dress best!

  20. Lots of choices here and it makes me tired seeing all the changes. You are a trooper. Love that the last two choices with the black without shoulder pads the best. Can’t go wrong with black or red. But if you aren’t comfortable, keep looking. Definitely cocktail length dress tho.

  21. I find 3/4 length sleeves to be mumsy, so I would suggest the black dress. It’s also just a little more fun for a party.

    1. I agree with you about the sleeve length. The dress is very flattering otherwise, but the 3/4 sleeves push it into “mumsyland”

  22. My favorites are the burgundy velvet, silver keyhole and last black sequin,in that order. I don’t like the red, it just doesn’t seem festive enough, probably because we’ve been seeing so much red all season.

  23. Love this post and your even trying dresses out of your comfort zone. IMHO, the Alex Evenings Embellished Ruched Sheath Cocktail Dress in red is the clear winner but I’d skip the black hose and shoes in favor of champagne evening shoes and bag with a not-black faux fur jacket. It’s stunning on your figure and in it you have a fantastic Old Hollywood glam vibe. I also agree that some dresses are just too low cut!!!🥹🤣

    1. Yeah, I really like the neckline on the red. It’s high, but wide, so it works. In fact, I probably need a strapless bra, which is definitely a point for the Con column. I agree on ditching the black hose with the red dress. I didn’t think about a non-black fur jacket. I have this one. I might see how it looks with it.

  24. I agree the two finalists are the best of the bunch — but definitely not black hose with the red dress.
    I would choose the red over the other one, but you should keep looking.

  25. Really like both the red and the black sequin ones!! You look so pretty in both of them! Wear what feels best to you!! We’ve all learned that trying to make something work, just doesn’t!! Have fun at your event, it sounds so exciting – holiday party in Chicago!!!

  26. I really like the fabric of the black dress and agree that removing the shoulder pads is an improvement. I also like everything about the red one except for the side embellishment. However, I keep hearing you and other influencers saying, “If you don’t love it, don’t have it in your closet!” Hopefully, you still have time to keep looking for the dress that you love and that Paul really likes on you.

    1. I know, and that is what bugs me. I have something in mind, but I don’t know what it is. But then, I do have a few suitable options here, so if I don’t find anything better, it’s all good.

  27. I think the red looks best, and also looks like a holiday dress. I have been shopping for cocktail dresses and have concluded that I feel like a very covered up dress with long sleeves makes me feel unfashionable. Many of the styles are very bare, including strapless and sleeveless and I don’t like that style. I have settled on a cap sleeve sheath dress that is sparkly. That way I have something interesting but it’s not covered up. I also do not like the dark hose.

      1. What about this dress? It felt young but not too bare to me

        Vince camuto cap sleeve embellished dress. Nordstrom. Can’t get it to paste!

  28. I agree with Lisa, maybe the mental block is coming from no desire to wear a dress this year. A sequin maxi skirt with a pretty top with sheer sleeves, or even a jumpsuit (difficult to find I know, but can be so chic and stylish)–something different! The struggle is real, but there’s something out there!

  29. I love the Vince sequined cocktail dress – it’s the right blend of festive yet sophisticated. I’m not a fan of any of the red dresses (truth be told, I’m not a fan of red anything). I also like the Vince fit and flare. It looks fun and fresh. In either case, I’d opt for strappy heels as opposed to pumps with block heels, which lean to boring and office-like. Pumps with stiletto heels might work, if they have a sexy vamp.

  30. First, thank you for sharing your struggle and being so real! I love it! Now for the dresses…I love the red on you! It fits you like a glove! I would do a nude tight instead of black. The black definitely looks better without the shoulder pads, but that red is gorgeous on you!!!

  31. You do really well picking outfits and I’ve seen some really nice dressy dresses on you. None of these feel or look like THE ONE. Keep looking.

  32. Go with the red, it’s your color and very festive. Can you go with like a champagne hose instead of black with nude shoes?

  33. I’m in search of a dress for a black tie optional winter wedding so I appreciate the post. I like the red dress better than the black. I can’t really pinpoint why I like it better but I do.

    Good luck!

  34. I agree with everything you said about each dress. I like the last dress without the shoulder pads. I like the burgundy side ruching dress better than in red. You look great in it. After reading this I now know why lately I don’t like my sheath dresses anymore. I can’t find dresses I like anymore because they are either too juvenile or matronly. I do better with T-shirt dresses or sweater dresses. I have a high waist and long torso too but not long legs like you. 😞

  35. I love the red dress on you and great Christmas dress. However i dont think it looks good with the black hose. I think skin color or slightly darker hose would look best. I would have someone take that pin off the side if that’s a possibility.

    1. Yeah, I just can’t get excited about that one. BUT, maybe I should try more with silver sequins. I like that aspect of it a lot. Seems more fresh and modern than the red, black, burgundy, and green.

  36. Ohmigod I juuust went thru this with buying a dress for a wedding and i thought the same thing—why dont my “go to” sheath dresses work?!? i agree that the red in the smaller size looks better and the black without the shoulder pads. But i gotta say, that Vince Camuto metallic looks fabulous on you!

  37. You have a lovely figure, so I like the dresses that are form fitting, especially the red one and the Vince Camuto emerald green. If you really don’t like the asymmetrical hem—which I do like!—could it be altered so the hem is even? It really is pretty and festive. I like the long-sleeve wine colored dress, too, but thumbs down on the jumpsuit and the poofy skirt. Have fun at the party!

      1. Your two contenders are lovely but each have their flaws IMO. The red shows off your figure, is festive but unfortunately has way too much fabric going on. The black is a dress that I would wear at age 70. Covers saggy arms, poochy stomach but I’d still feel good in it. I’m from the Chicago area (snowing today! ) and have attended my company’s formal Christmas events for years. The weather never stopped the younger women from wearing sleeveless or more bare dresses. I think the green velvet was stunning on you. Really showed off your figure, beautiful color & the asymmetrical hemline looked very modern & dressy to me. Enjoy those slender arms while you can! I understand if it just doesn’t do it for you. Good luck!

  38. Wow, so many choices! I actually love the green velvet on you most, although I know you don’t care for the hemline. The two finalists are both nice, but I agree you could do better. Feels like the right cocktail dress should be an instant “wow, this is it!” It doesn’t sound like you feel that way about either.

    Not sure if it’s dressy enough, but I keep thinking I want to try that velvet floral Evereve dress. The coloring would be gorgeous on you, although reviews are a bit mixed.


  39. You usually know yourself so well and I have learned so much from you! I only thought these 2 were options also and I prefer the black without the shoulder pads. Refined and elegant!!

  40. I LOVE the red dress on you! I agree with the others that the black hose and shoes are too harsh. Silver metallic shoes might look nice and coordinate with the embellishment at the waist.

  41. If you are going to a black tie affair in Chicago, I would wear the black one for sure. I am from Chicago -where is the party at? Have fun!

  42. I like the red dress and the Pisarro dress. For some reason I think there’s something else out there for you? i really like the Sam E. green velvet dress too? I get the hem length too. I realize time is probably of the essence and you have to decide soon. It seems like lots of dresses for women of our age (50’s) just seem so matronly or lol as you said grandmother of the groom.

  43. Honestly think they are all too old fashioned. Of them all the final black is probably the best, but I think you need a more current look. Honestly think there is so much more out there that is better. Sorry!

    1. I agree with Michelle. The very first black sequin one and the silver one are the only two that I think have a modern style to them. All of the others feel like what we’ve all seen for years. I know you didn’t like the shoulder pads on the first dress and I agree they are *too much* but I think the shape of the dress looks very current and un-matronly. I know it isn’t form fitting but that allows your great legs to take center stage! To some extent I think it is the form fitting style of the other dresses that makes them feel dated to me. If you’re going to go with any of the ones from this try-on I think the final black dress with shoulder pads removed is the best. The red fits you beautifully but something about it just feels sort of off. What about trying some other colors like champagne or navy for a twist on the traditional Christmas party look? Thanks for sharing the trials and tribulations of your hunt!

  44. I really like the last one, VInce Camuto black without the shoulder pads; it looks more youthful without trying too hard. I loved the green velvet one but sleeveless can be a drawback sometimes. The comments your daughter makes sometimes cracks me up!

  45. I REALLY appreciate you trying on all those dresses, what a feat! Between the 2 contenders, I think the red is more festive. Can you try and return things on from Rent The Runway? I don’t envy your predicament. I am grateful my holiday party circut will include my husbands Italian car club party where at 53 yrs old I will most definatley be one of the youngest in attendance. I am excited to see what you choose.

  46. Cindy styled a really cute velvet dress from Kohl’s about a week or so ago – you might try that one. Black is too low cut and Red is ok.

  47. Oh this challenge! Went to a wedding in Chicago last December that was semi formal. I wore the Spanx nude fishnets you recommended in the past! With open to sandals, just folded the seam under my toes and threw away any thought of wearing them again. All the young people were wearing open toe shoes – not at all strange. For the record, at first glance, the red dress fits you beautifully. I understand your avoidance of “matronly” because I do the same. You look great in both dresses, I lean to the red dress for first glance appreciation of fit. Keep looking if you want, knowing you have great choices already! And don’t worry about wearing closed toe shoes. It was really no big deal!!!

  48. I Ike both of your finalists as well as the burgundy with side embellishment. The black looks the dressiest and is VERY flattering. (Without shoulder pads) You look beautiful in all of them.

  49. I think you found the two that are the best, but I still think you can do better. If I have to choose between the 2, I vote for the black. Good luck. I despise dress shopping!!

  50. Black one!! It totally looks fantastic!! It also fits the cocktail/black tie optional dress code.

    The red one is totally more business dinner attire.

  51. I think you can do better. My recommendation is to stick with the style that you know is most flattering for your body, but instead of black or a traditional Christmas color, look for something unexpected, as I’ve noticed you prefer that in your less formal holiday attire. I think that will also help you to feel more modern and less matronly.

    1. I get that, I typically do not like to wear red at Christmas, but I felt like a red dress has a certain wow factor that is different than the predictable red sweater + black pants. And it’s a trending color this season. But I think the combination of red with a traditional style is that is throwing this one off. If I do red, it needs to be in a more modern way. And black is always safe and I love it and it looks good on me, but yes, so predictable. It also needs to be a more current style to look modern in the way I want to present myself. I think I need to look for a satin fabric with some more trendy elements. I’ve ordered a few more options.

  52. Ohhh I’m probably going to blow our friendship to smithereens here …. These are all a {hard} pass. Most of them you are not old enough to wear. I’m excited to see round 2 of the Christmas party dress search!

  53. Hi Jolynne! I really like all of these drssses but like the red dress the best. I’m struggling just as you are for exactly the same type of event also in Chicago! I haven’t read all the comments so someone may have already said this, but have you thought about a sequined skirt with a blouse or sweater? I’m considering this type of look as I’m thinking it may look more current and less as you’ve said “matronly.” Not you look that way all!!! But I do understand the way you are feeling!!! Thank you so much for sharing this post!! Blessings! Krista

  54. I agree that if you chose from this line up I’d say the same two you posted at the end. I like the black one better than the red and for sure without the shoulder pads. But, I also feel you should keep looking. You’ve had some really nice dressy dresses over the years for weddings I’ve loved on you. Since this is a work party, probably no one would know if you wore a dress you have. I think one was black and one blue if I’m remembering right. The black one here is just alittle too low. Anyway to sew it up some….. higher?

  55. Sequence one for sure. The red one is ok…but maybe too Christmas predictable. It’s missing pizazz. The sequence one is fun but also classy.

  56. I thought the side ruched burgundy velvet with those uncomfortable heels (Lol) was elegant. The velvet kept it from being a matronly fabric. Your heels so complemented the side broach! I thought the black sequin looked like just any “off the rack” dress that is sooo common!
    The red in the 8 fit better than the 10. Once again, I loved the uncomfortable shoes! Dresses are the worst to shop for. Good luck

  57. These are definitely the best two of what you tried. And I definitely vote for the red… I’m not at all a fan of black for cocktail parties because that’s what 95% of the women are wearing so to me it’s boring. 🤷🏻‍♀️ As good as I think the red looks, I think you’ll find better 😊

  58. You look fabulous in both !
    Red dress-sexier, very figure flattering, vibrant, younger look
    Black sequins – without the shoulder pads is a definite win! Classier , more elegant, and Richer-looking all around

  59. Did you see these two? The first one is more your traditional sheath style but the off the shoulder neckline keeps it from looking matronly. The second is a totally different cut but still a straight shape vs A-line or fit and flare. I agree with others that it might be worth doing a second round up. Keep us posted!



    1. I’m not a big fan of off the shoulder dresses on me because it creates a horizontal line across one of the widest parts of my body. But I love the idea of that Eliatt dress! I ordered both; it can’t hurt to try!

  60. Also this one is a similar cut to the one Beth suggested, but in a red satin.

    1. Yes, I like that. I think one of the issues I’m having with the dresses I ordered is the fabric. Satin is trending right now, and the drapey styles are too… It just looks COLD to me. But I’ve ordered a few to try.

  61. I like the black best, but having seen enough of your try-on posts to know what you dislike, I think the low cut neckline will bother you in the end. I don’t think any of these are it, sadly.

  62. The red dress is the winner in my opinion! Festive and fits you perfectly! The color compliments you and is not showing too much cleavage. Not a fan of it with the black tights, though. You would need a different option. I am looking for an outfit, too, for my work holiday party. But I just can’t do the dresses as its way too cold out! lol

  63. Hi,
    Thank you for sharing the struggle so many of us have experienced.
    I agree, the black or red is your best option.
    I have this fantasy that SOMEONE is going to step up and offer a full like of flattering, fashionable clothing for the woman over 50.
    You sharing your struggle ,helps us realize, it is not just us….
    Hope you feel good and have a great time at your event…

  64. I vote for the last one (black sparkly Vince Camaro) with out the shoulder pads. But, actually, YOU look great in everything you showed us!

  65. Had to shop for a late November wedding ,a couple of years ago, and know how challenging this is.
    Now Im on a mission with you lol

    came across this one and thought it could work …


  66. I love the final two, but my first choice is the black. I think it’s a little more black tie and a little more current. If you’re still looking, try Dillards or Von Maur.
    And, which one does your husband prefer since it’s his company party?

  67. I really like the red dress. I would be interested to see what it looks like with different shoes, etc. like you said.

  68. Go with the black dress you cut the shoulder pads from. Having voted for that one… I really liked the style of the dress your husband didn’t like 😂.

  69. I like the red one. I think it is the sleeve length on the black one that is off. You look better with a shorter sleeve. I really struggled this year too. Both my party and my husbands are less formal so I ended up with an emerald green silk skirt and a matching emerald green sweater. I’m going to wear some sparkly jewelry to amp it up.

  70. You are more a pants person than a dress person – are pants a possibility? Like wide, flowy velvet or satin pants, with a fancy top and great heels? You do need to be a little careful with the M word with this look as well, but I feel like I’ve been seeing lots of good options for velvet or satin pants that look very current and chic.

    1. I don’t look that good in flowy pants, though. I love a good velvet bootcut or flare, but that’s not really black tie optional attire, unfortunately. I like dresses, but I find them a lot easier in the summer than winter.

  71. I personally dont like black hose with the red dress. I would wear nude. Both dresses look very nice on you especially now that you removed the shoulder pads from the black one.

  72. You look gorgeous in both but the red absolutely is my favorite! It is so fun and eye-catching and festive. You will stand out in the best possible way in that dress. 🙂

  73. It seems like the dresses are all the same, year after year, nothing new. None of them wowed me. I would say the red dress is your usual look so if it makes you happy then that’s what matters:)

    1. Yep, I feel the same. Too much of the same. But that’s what I ordered… there are lots of other options out there, but these are what resonated with me. Until I tried them on, anyway, ha! I’m still trying…

  74. I personally thought that the Pisarro dress was the best looking dress on you. It is very flattering on and the color is beautiful!

  75. A vote for the black sparkle – including because you could get the red, too, and wear it to dinner or a show but the sparkle is fun for an event. I also really liked the green dress on you. In the end whatever makes you happy right?! 🙂

  76. Vos robes, à mon sens sont trop prévisibles,trop attendues .
    Personnellement je choisirais un modèle midi .Plutôt une jupe noire ,en mousseline plissée, avec un haut a sequins noirs ,avec un décolleté bardot par exemple , ou un haut corset a sequins multicolore. Il faudra porter des escarpins a talons hauts.
    En France nous avons le culte de la petite robe noire ,très discrète ,dont la beauté repose sur la coupe et la qualité du tissu .

    1. Je suis d’accord et j’adore l’idée d’une petite robe noire élégante avec des diamants scintillants et des accessoires.

    2. I love hearing your perspective. And I agree that these are all too predictable and expected. Unfortunately, that seems to be what works best for my body type! But I’m willing to sacrifice the perfect proportions for something that makes me feel more modern and fun. I’m still looking. 🙂

  77. I read this last night and thought I commented but couldn’t find it (reading on my phone still makes everything go into one long column on the left). Anyway, I just reread the whole thing more carefully and wanted to comment that I’m not sure any of these are the best choice. I DO think you look fabulous in red though and it’s a Christmas party after all so why not be festive-in-red. Black sequins are more of a NYE dress to me. What struck me is how short all these dresses are (if I tried them on me they’d be mini-dresses) and why all the 3/4 length sleeves which is what makes the dresses more matronly I think. I also need a dress for a holiday party (not black tie though) but it got me thinking about one important element: Who’s your audience? I always try to think about not only the location, but who’s going to be there. Is the crowd likely to be trendy? Are they your age? Older? Younger? Does that make sense? I saw one of your followers comment here about wearing booties like the younger crowd does with dresses, but if it’s a fancy holiday party with 50+ year olds and a more conservative crowd I would definitely not wear booties. Anywho…..I hope you find the right dress and can’t wait to see more of your try-ons! 🙂

    1. Absolutely, I always try to consider my audience when choosing what to wear to pretty much any event or occasion. This is a conservative industry, and the company employs a range of ages, but the people we will be socializing with are older. It’s also in Chicago, so I assume more dressy than what I’m used to here in the Philly suburbs.

      I’m sure any of the dresses I tried would fit in, but I don’t feel like any of them quite represents the modern/urban components of my personal style.

  78. Good post! And no, it’s not a unique challenge in your 50s (unfortunately!). Wait until you are in your “youthful” 60s and imagine being a mere 5’2″. Not a matronly 60, but a young 60 with a reasonably good figure all things considered. As an event co-chair for an upcoming museum gala event, I’m really struggling to find something appropriate yet stylish. Probably pulling out what I wore 2 years ago and will hope no one notices!

  79. I think the black is more fun. I agree they both fit your body well, but the embellishment on the red would bother me. Can you take it off? Bonnie

    1. I wouldn’t want to mess with that, but I did get another one in today that I am curious to try that is similar but with no embellishment. I think it still looks too mature for what I want, though.

  80. Jo-Lynne,
    After reading through the comments, I see we’re as much help as your husband and daughter! Ha! The American Girl doll comment made me laugh out loud! 😂
    A. Know that you couldn’t on your least favorite of all of these and still look better than anyone else in the room.
    B. Keep looking.
    C. I’d love to see you in this: httpss://www.nordstrom.com/s/7345189?color=002
    D. Have a great time at the party!

  81. This may be an unpopular opinion, but, I think that the red and the burgundy are both really matronly. I think it is the beaded accent at the hip combined with the sleeves and the ruching. It just seems like something a woman 20 years older than you would wear. I also do not like the ruching with the short fur jacket. Something about the visual seems off. That being said, I love the black sequined dress on you without the shoulder pads. And, the more I come back and look at the pictures of the green velvet dress, the more I like that one too.

    1. I hear you on all counts. I feel like the black sequin (no shoulder pads) is a good backup, but I’ll keep looking in the meantime. If I don’t find something I like better by next weekend, I’ll start figuring out shoes/accessories that I like with that.

  82. I went through the same thing 4 years ago when trying to buy a mother of the bride dress! They all seemed old looking and too matronly on plus very heavy! So I finally went into a boutique with my daughter and found the perfect dress when I had given up hope to finding what I had visualized in my head I actually found it!
    Satin and velvet are having a moment have you considered a satin dress?

    1. Yes, I’ve gone back and ordered satin options. I think I didn’t gravitate to them at first b/c they look cold to me, and it will be Chicago. But I do think I need a softer fabric than what I’ve been trying.

  83. I attend several formal work-related events each year, and choosing a dress can be a struggle! WHBM has some nice options, here are two worth a look:


    1. And one more from Bloomingdale’s, the sheath shape you prefer with some modern details:

  84. Holiday dresses are hard.
    Your try ons really ran the gamut, and not a keeper in the bunch.
    The red ruched sheath looked the best on you….but I will tell you that my mother wore that style cocktail dress in the 90’s complete with the embellished piece over the hip.
    Sequins just scream dance recital to me ….just way over the top rather than flattering, or elegant.
    Lately in Boston & NY the trend has been soft metallics or mesh of lighter weight with metallic threadlines.
    Even structured sheaths, and form fitting pieces are in softer fabrics. soft velvets even
    I know I feel like I’m looking at the same dresses every year… You look so good in form fitting dresses sometimes something simple in an unexpected fabric or color or shape can surprise you and turn out to be just perfect. Like a higher neckline with a “V” back? Good luck

    1. “The red ruched sheath looked the best on you….but I will tell you that my mother wore that style cocktail dress in the 90’s complete with the embellished piece over the hip.” Okay, that is all I needed to hear, lol! I will find something else.

      “Lately in Boston & NY the trend has been soft metallics or mesh of lighter weight with metallic threadlines. Even structured sheaths, and form fitting pieces are in softer fabrics.” That is the realization I’ve come to. The fabrics and structure of the dresses is what looks dated to me. I have ordered some satin options and some with softer lines.

  85. I went through all the dresses on you and when I saw the red one and the other black you narrowed it down to, they were both winners in my opinion. The red one is my favorite on you though!! I did agree with all the faults on the other ones, before I even read what you said was wrong with them.

  86. You look great in the last 2 but I think you can do better. In my opinion, they both sort of seem a bit outdated. Can’t put my finger on it but they don’t seem modern or understated enough. However, with that said, you look good and I am just so picky about making sure i LOVE what I buy now that I am over 50. Thanks for always being so open to comments & suggestions. You are so helpful.

  87. I think the 3/4 sleeves look matronly. The long sleeve dresses look more on trend. The black sequin dress has my vote with nude stockings and different shoes.

  88. Between red and black, I’d chose the black dress. Unpopular opinion – I really liked the Eliza J silver dress the best out of all of them.

  89. Of all these dresses, I like the black sequinned Vince Camuto on you the most! It is fresh and fun, not stodgy, and very festive. You can wear black hose with it and black shoes, and look fabulous! If you keep looking, I suggest trying Bloomingdales, Dillards, and Anthropolgy, for some different points of view. Thanks for doing this for us!

  90. Random question, you mentioned selling the black one after you cut the shoulder pads out. Do you sell your gently used clothing locally or online? I’m the same size as you with similar proportions and would definitely shop if you sold them online.

  91. I like the red one, but it looks a little strange at the neck. I also like the length way better than the black. I’m 63 and once loved shorter dresses, but now, and even at 50, I think a little more conservative looks classier! My favorite for you was the burgundy one. The large embellishment was a little weird for me, but not a “deal-breaker”!
    Some of the clothes you say are not your style actually look good. I do think you need to step out of your comfort zone! You styled a casual, white, collared blouse some time ago and commented it wasn’t for you. It looked great.

  92. I think you look great in both; to me your legs look longer in the black but I like the red’s festive color. I wore a dress similar to the red one (but in blue and with bell sleeves) to my son’s wedding last year and it was my favorite dress ever, but there you go, I’m a matron for sure.

  93. Jo-Lynne… TheRedTheRedTheRed. It fits you so well. No substitute for that. I get it about the embellishment, and for that reason you could keep looking. But as a back-up, the red is more than acceptable. Forget the black one. It’s fine but a distant second to the red. Forget about the dresses for a week or so. Then go back and look at these pictures and I think you will see the clear winner.

  94. I loved the black one. My question is what tights are you wearing?

    I am with you on the rest of them I would’ve returned them also!!

  95. Between the last two I like the red best. But, I really like the Pisaro one. Maybe not with the black pumps. What do you think about trying it with nude or gold shoes? It looks like it has gold in it.

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