Winter Fashion Try-On Haul: Holiday Party Looks + Winter Sweaters

Happy Friday, friends! I’ve got another winter fashion try-on haul for you today. This is mostly holiday party looks and a few more casual winter sweaters. And yes, even more cocktail dresses!

I got a few more in and took pictures before I did the photo shoot for yesterday’s post. Even though I didn’t keep any of the latest additions, you might find something you like in here.

Winter Fashion Try-On Haul: Holiday Dressing

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.

First up, some fun holiday tops, casual winter sweaters, and a versatile sweater dress!

Carla Velour Top

at Evereve (S) // AG Mari (29) // SE booties (8) // old J.Crew earrings

This blue velvet top has such pretty details. I appreciate the length; it’s short enough to leave untucked, but you can give it a front tuck if you want the effect. The v-neck is flattering, the smocked cuffs are really fun, and the puff sleeves don’t even bother me.

I paired it with washed black straight leg jeans, and I added black suede pointy toe booties to elongate the line of the leg and keep the dressy-casual look going. The crystal statement earrings make sure it looks holiday-festive.

VERDICT: Keeping! I’m sure I’ll find an opportunity to wear this.

LOFT Ruched Ruffle Neck blouse

at LOFT (S) // GF velvet flares (29) // Marc Fisher boots (8)

This green blouse looks way more expensive than it is; and I love this rich green color.

I paired it with black velvet flares and black leather pointy toe booties above, for a more casual-chic holiday look. And then with luxe black pants and black suede pumps below, for a more classic, office-ready holiday look.

VERDICT: Keeping!

J.Crew Ribbed Cashmere Turtleneck Sweater

at J.Crew (S) // MOTHER Dazzler (29) // LØCI Origin logo-patch sneakers (8)

I love the styling on this sweater, although I wish it weren’t quite as roomy through the body. It fits me the way it fits the model, but I feel like it would look better a size smaller.

That said, the ribbed knit, raglan sleeves, and funnel neck are perfectly lovely! Plus, the luxe cashmere is simply divine. I just wish this pink color weren’t quite so bright.

VERDICT: Returned it; I might re-order in the XS in a more subtle color.

Adia Sweater Dress in Morning Fog Heather

at Banana Republic (S) // boots (8)

I’m a big fan of a sweater dress in the winter, and this one has great details. I love the design in the stitching, but it’s a little snug. It’s also a tad shorter than I prefer. I wonder if I’d prefer the medium.

VERDICT: I returned it; I might re-order in the medium. It would be nice to have for the winter.

Waverly Off Shoulder Jumpsuit

at Evereve (S) // Marc Fisher pumps (8) // Ettika earrings

So, this is a fun holiday look. I like this jumpuit way more than I expected, but I don’t get the off-the-shoulder thing. I like it better on the shoulders, I think.

It’s stretchy and comfortable, and it slips easily on and off. It has just the right amount of drape, and I love the subtle sparkle to the fabric.

VERDICT: I would totally keep this if I had the right occasion to wear it. I just don’t know that I do, and I’d hate for it to go unworn. I might keep it for a week or two, to be sure, but I’ll keep the tags on if I want to return it.

Sanctuary Perfect Sequin Top

at Evereve (S) // GF velvet flares (29) // Marc Fisher pumps ???

I think I tried this top last year and didn’t like it, but for some reason, I like it more now. Maybe I paired it with straighter pants; it looks really good with these velvet flares.

The sleeves are still a little wide, but it sort of works. I’m not sure I like the pumps, though. I might prefer pointy toe booties.

VERDICT: Holding onto this one for a while; it might be nice for NYE, or a holiday concert.

Save The Duck Bridget Reversible Faux Fur Hooded Jacket in Burgundy Black

at Nordstrom (S) // Jenni Kayne sweater (S) // MOTHER Hustler (29) // Vince booties (8)

This jacket caught my eye as I was wandering through Nordstrom last week. I love the color, and it is soooo luxe and soft, but it has a rather swingy silhouette, which I’m not sure I like. It’s reversible, too. I left it there, but I wanted to share it in case someone might like it.

Vince Faux Shearling Coat in Fig

at Nordstrom (S) // Jenni Kayne sweater (S) // MOTHER Hustler (29) // Vince booties (8)

This fig color must be in this season. This is another faux sherpa (shearling) jacket that caught my eye.

I love the longer length and one button closure on the front. It has such a nice, minimalistic styling, and it’s soooo warm. I feel like it would be perfect for my Chicago trip this weekend, but it’s also very pricey, so I couldn’t commit.

VERDICT: I’m still thinking about this one. I might put it on my Christmas list. Paul is always asking me what I want, and I never know what to tell him other than jewelry.

Michael Kors Stand Collar Walking Fur Coat

at Nordstrom (S) // Jenni Kayne sweater (S) // MOTHER Hustler (29) // Vince booties (8)

I also tried this shorter option. I like the color, and it’s super soft, but sorta shapeless.

VERDICT: I didn’t bring this one home either. The one I did bring home, for some reason, I didn’t get a picture of. I will photograph it later this week!

Sundry Stripe Crew Pullover

at Evereve (1) // MOTHER Weekender (29) // Vince boots (8)

So this sweater is kind of fun. I love the color combo, and I’m kind of tired of neutrals and solids. It’s thin and stretchy and soft.

To be honest, I’m not sure the price matches the quality; but I do love the fit, the style, the length, the colors, and the design.

VERDICT: I’m undecided. I like it, but I’d prefer to get it on sale.

A Few More Holiday Party Cocktail Dresses

Okay, so I know you thought I was done with holiday dresses, but I tried these on before I took the pictures for yesterday’s post. I figured I’d share them in case anyone is looking for cocktail dresses for upcoming weddings or holiday events.

I also took pictures of the top 3 contenders with a few different shoe and accessory options when I was showing them to Paul and trying to decide how to style them.

Aidan Mattox Satin Sheath Midi-Dress

$50 off at Saks (8) // Stuart Weitzman heels (8) // Ettika earrings // J.Crew bracelet // Loeffler Randall bag

I love this idea of this one. The fit is perfection, it aligns with my personal style goals, and the color is gorgeous. I also love it styled this way, however, it does not look like a holiday party to me. It’s perfect for a wedding guest dress, though!

I would probably have it shortened an inch, if I were to keep it, but I like the ladylike below-the-knee length.

If you need one, and this aligns with the level of formality for the occasion and your personal style goals, grab it now!

SALE ALERT: Use code SHOPGCSF for $50 off the dress and this bag, and FREESHIP for free shipping. Also, these shoes are marked down to $296.80 from $495, the bracelet is 40% off with SALETIME.

VERDICT: Sadly, this got returned. I’m not one to keep dresses like this “just in case” because I don’t have many semi-formal events to attend.

Aiden Maddox Cowl Neck Cocktail Dress

$50 off at Saks (8) // 25% off at Bloomies (8) // Stuart Weitzman heels (8) // Ettika earrings // J.Crew bracelet

This dress is by the same designer, and I think it’s the same material, but I do not care for the design at all. That cowl neck thing is overwhelming me, and I prefer the way the skirt is designed on the first one.

SALE ALERT: Use code SHOPGCSF for $50 off the dress, and FREESHIP for free shipping. Also, these shoes are marked down to $296.80 from $495, the bracelet is 40% off with SALETIME.

VERDICT: I’m not at all sad about this one; it’s also been returned.

Sachin & Babi Carmen Sequin One Shoulder Midi Dress

$50 off at Saks (8) // Stuart Weitzman heels – 35% off (8) // Ettika earrings // J.Crew bracelet – 40% off// old box clutch

This sequin one-shoulder dress is a huge splurge, and I’m not quite sure why I ordered it, given that it is most decidedly not my color. I think I was feeling desperate at the moment.

I was expecting such an expensive dress to fit like a dream, but it doesn’t do much for me at all. It is definitely going back.

SALE ALERT: Use SHOPGCSF for $50 off and FREESHIP for free shipping.

VERDICT: I returned this one yesterday.

Elliatt Cassini One Shoulder Dress

at Nordstrom (L) // Stuart Weitzman heels // Ettika earrings // J.Crew bracelet

I really, really wanted to love this dress. It’s the first one I ordered after I realized how frumpy and matronly I felt in the first batch of dresses.

To feel more current, I wanted to find a dress that showed a little more skin, preferably in a satiny fabric with some drape. Plus, I adore this shade of green. It makes me feel like a modern day Scarlett O’Hara.

After all, tomorrow is another day!

Unfortunately, the first one that came in was too small… and it was a medium. Talk about a blow to the ego.

Nevertheless, I persevered.

I told myself size is just a number (or in this case, a letter) and re-ordered in the large. It took for-ev-er to arrive, and when it did, womp… womp… I was underwhelmed.

I think I need a medium in the top and a large in the bottom. I guess I can thank breast reduction surgery for that, but that’s okay. I have no ragerts.

VERDICT: Back it went!

FRENCH CONNECTION Sonya Ribbed One Shoulder Mini Dress

at Bloomies – 25% off (M) // Stuart Weitzman heels // J.Crew earrings // J.Crew bracelet // Loeffler Randall bag

This dress has potential, but the fabric looks and feels cheap, and the big bow on the shoulder is not my cuppa tea. It’s cute, tho!

VERDICT: This dress is already on its way back to Bloomingdale’s.

Norma Kamali Satin Cowlneck Sleeveless Midi-Dress

$50 off at Saks (M) // Stuart Weitzman heels (silver)  // Ettika earrings // J.Crew bracelet

I was hoping that I’d love this one; it seemed like a nice alternative to the Norma Kamali strapless dress that I also like – simple and elegant – but still a little outside of my comfort zone (in a good way).

The satin fabric on this is right on trend, the drapey cowl and bias cut skirt is typically very flattering on curvy bodies like mine (curvy in body shape terms, not as plus-size) and the quality is there.

However, it just didn’t do much for me. The cowl is way too low (it’s more revealing in person) and it sits awkwardly over my hips and rear. I was already wearing heavy duty Spanx, so there’s not much more I can to to improve that situation, and I don’t like the neckline anyway, so back it went!

SALE ALERT: Use code SHOPGCSF for $50 off the dress, and FREESHIP for free shipping. Also, these shoes are marked down to $296.80 from $495, the bracelet is 40% off with SALETIME, and the bag is 25% off (no code needed).

Norma Kamali Diana Dress

at Bloomies (M) // Stuart Weitzman heels (8)

One of you, dear readers, told me about this Norma Kamali dress with the built-in Spanx. I was too curious NOT to try it, so I placed the order from my phone one night, and it came in record time.

It took me about 20 minutes to wrestle myself into it, which was a deal breaker in and of itself, but I also don’t really care for the style either. I feel like I’m wearing a toga.

VERDICT: Another dress on it’s way back! I bet the mail carriers love me.

Vince Camuto Embellished Cap Sleeve Sheath Dress

at Nordstsrom (10) // Sam Edelman Kia (8) // Ettika earrings // J. Crew bracelet // Loeffler Randall pleated clutch

I’m sure you’re sick of seeing these next dresses, but I tried them all on with different shoe and accessory options the night before my photo shoot with Alison, so I thought I’d go ahead and show them to you.

This was the first time I tried on this dress in the right size; it was too small in last week’s Try-On Haul. This dress is the easiest, most comfortable cocktail dress I’ve ever put on my person.

It just slides right on (it’s fully lined) and zips up the back, no special bra or undergarments needed. Easy peasy! I feel like it fits like it was made for me.

I like it with the gold sandals and black bag, and the crystal earrings. I wish I had the occasion to wear it! It just doesn’t seem to fit the office holiday party I’m attending this weekend.

VERDICT: I still have this but I will probably return it. I don’t attend enough fancy occasions to warrant keeping it “just in case.”

Eliza J. One Shoulder Velvet Dress

at Bloomies (10) // Stuart Weitzman heels (8) // J.Crew earrings // J.Crew bracelet // Loeffler Randall bag

This is the Eliza J. one shoulder velvet &satin sheath with the sparkly gold heels and the crystal embellished baguette bag. I like it, but I’m afraid the shoes and bag look too matchy-matchy.

I love it with my black & rhinestone embellished heels from a few years back, but the 4″ stiletto is too much for my aging feet.

Plus, you can’t see it here, but the rhinestones on the shoes read silver, and the bag (as well as the metal in my jewelry) are gold.

I brought out these Sam Edelman Kia gold heels from last summer to go with the Vince Camuto metallic sheath, and I love how it pairs with the baguette bag, so I thought I’d try them with this dress.

In these pictures, I feel like it works, but I’ve been second guessing them after seeing the pictures in the post on the blog yesterday. I’m not sure they’re quite dressy enough.

VERDICT: At this point, this is the dress (and the entire outfit) I’m planning to wear, although I won’t lie. I’m scheming ways to shop for different shoes in Chicago.

Norma Kamali Strapless Midi Dress

25% off at Bloomingdale’s (M) // at Revolve (M) // Stuart Weitzman heels (8) // J.Crew bracelet // Loeffler Randall bag

This is obviously the strapless Norma Kamali dress, and I wanted to try it on again with and without a necklace.

A few of you suggested in last week’s try-on haul that it might look better without, so I was curious to see how it looked both ways.

I like it much better with a necklace, but it still felt kind of bare, so I tried it with my grey faux fur capelet.

I also swapped out the sparkly sandals for the matte gold ones, and I feel like the combination works really well with this whole look. The visual weight of the cylindrical heel offsets the more bulky faux fur capelet, but I still feel like the color of the fur looks old fashioned and a little mumsy.

Next, I tried it with my black faux fur jacket… I don’t know, it all kind of blends together in this dim lighting.

That’s when I thought about my silver wrap. At first I thought I liked this option, but it’s fussy and sort of hides my shape.

VERDICT: I still really want to like this dress, but it’s just not coming together with the accessories, and I feel like it’s more trouble than it’s worth.

Reiss Macey Cutout Long-Sleeve Velvet Maxi Dress

at Bloomies (6) // Marc Fisher pumps (8) // J.Crew bracelet // Loeffler Randall pleated clutch

I had pretty much decided to wear the one shoulder dress when this dress arrived. Initially, it seemed to solve all the problems the others presented.

size 6

The long sleeves would keep me warm, the body-con styling is super slimming and figure-flattering, but also thicker and a little more forgiving than the fabric on the Norma Kamali strapless.

Reiss makes a really nice quality dress, and the cut-out detail and midi length are both modern and in keeping with a black tie optional dress code.

But it does something really weird in the back. See how it wrinkles, almost bubbles in the back, at the waist? Basically, the dress is too long in the torso for my short-waisted self.

size 6

It’s also verrrry snug in the size 6, which is what I’m wearing above.

The size 8 fits better, but it’s even longer in the torso. It’s hard to see here, but it sits weirdly at the neck and shoulders, as well as doing that bubble thing in the back.

size 8

When the size 6 came in, I tried it with a few different shoe/bag options, trying to convince myself it was a contender.

The silver SW Strapeze heels and J.Crew sequin bag seems to be the most modern option, as silver is very “in” right now, as are the oversized sequins on the bag, but something about those shoes in the silver really bugs me. They seem to illuminate how pasty white my feet are, lol!

size 6

The black pumps and black bag look nice, but they’re rather predictable, and I feel like they’re too conservative for this dress.

I love these Stuart Weitzman 4″ heels that I keep hanging onto because I can’t bear to part with them, even though I can barely walk in them. They seem to go perfectly with just about everything.

I especially love them with this feather Santorini bag. I mean, how fun is this!?!

But at the end of the day, I don’t love the fit on this one, and I feel like the cut-outs get lost in my hair. I’m not good with putting my hair up, and I don’t really want to spend the time when I’m in Chicago visiting a Drybar to have it done for me.

I think I’ll just stick with the one shoulder black dress and the accessories I photographed with it for yesterday’s post. If I end up shopping at all when I’m in Chicago, I might look at other shoe options, but I’m not going to stress over it.

And that, my friends, is a wrap! I hope you all have a great weekend!

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32 Responses

  1. I absolutely love the white sweater dress/tan boots on you. I don’t think you need a bigger size. It is very flattering

  2. I never comment but have to say that of all the dresses you posted the one shoulder was, IMO, the most flattering!!! Great choice and you’ll look awesome in it. Have a great time at the event 😊

  3. I’m actually really sad you didn’t keep the blue. It looks fabulous on you in a way that none of the others do. I’m going to try and make an argument for you to repurchase 🤣

    1. Blue isn’t any less of a “holiday color” than black… in fact I’d say it’s a lot more festive and it IS a holiday color (Xmas isn’t the only holiday this time of year).

    2. The pain (at least it looked painful to me 🤣) that you’ve gone through in finding a dress for this event is exactly why I buy event dresses when I see the perfect thing and have no event. I then have the perfect thing to reach for when that event comes up. I think you should absolutely have this dress available for the next event.

  4. The white sweater dress with the boots! This is one of my favorite outfits on you. I always love winter white and this dress fits perfectly and compliments your coloring.

  5. Jo-Lynne,

    The colors of those jewel tone cocktail dresses look stunning on you. (The cobalt Aidan Mattox Satin Sheath Midi-Dress, the emerald Elliatt Cassini One Shoulder Dress, and the ruby French Connection Sonya Ribbed One Shoulder Mini Dress). My favorite of them is the cobalt blue one, and the style looks fantastic on you as well.

    The Eliza J velvet one shoulder black dress you chose for your event is winner. Sophisticated and perfect for the occasion.

  6. Wow. That is a lot of work to do post like this. I don’t know how you manage all the orders and returns. Your credit card must be crazy to keep track of. I think you made the perfect choice for your outfit for Chicago. Don’t stress on the shoes. It looks great. No one is going to pick your outfit apart but you. Just enjoy your trip. Can I ask why his holiday party is so far from home?

    1. Yeah, I’m sure you’re right about the shoes, and I’m not stressed. If I find something I like better, that’s fun, but if not, I’m good! Paul’s company has offices all over the country, and he works with the Chicago office a lot, so he was invited to their holiday party this year.

      1. Yes…. Could be fun to shop for shoes there. I love shoes. That is neat you get to attend this party. How fun. Enjoy.

  7. Red looks so good on you and I liked both red dresses.
    Some of the dresses, Norma Kamali and the Aidan Mattox Satin Sheath Midi, make you look like an Hollywood glam movie star from decades ago. I mean that in the most positive way. Sapphire blue is another great color on you.
    I do think the Eliza J dress is a fantastic choice. I’ll be curious to see hear if you find different shoes in Chicago.

    My experience is that a lot of J Crew’s sweaters run roomy in the body. I do they need to work on their sizing.

    Enjoy the weekend.

  8. I love your blog & especially the try-on posts. I have one request though: if you don’t like the garment you are trying on (for whatever reason), could you not make a face & just smile like normal? There are times that I really like what you have on, but when I see the funny expression on your face, then I start second-guessing if it would look good on me. I’d just like to read why it doesn’t work for you in your written description, but let us look at the style in the picture without the negative influence of your expression. I would appreciate that.

  9. I liked some of the first batch of dresses you posted but that black velvet dress that you plan to wear is absolutely stunning! Clear winner.

  10. I like the blue and green tops and the velvet flares a lot. Same for the cream dress and boots. I still like the one shoulder dress best of all. I really don’t like midi dresses that are narrow at the bottom. They make my hips look bigger but maybe that’s the point to create that hourglass body. I think you went with the right choice. I think the shoes you picked are good. No one’s going to be looking at your feet. They’ll be looking at your beautiful face and hair. Have fun.

  11. I love the sweater dress with the boots! And that pink sweater is a nice change from the dark colors we often wear this time of year!
    I’ve been looking at sweaters that very color!
    Definitely put that fig colored coat on your wish list it looks so cozy and warm!!!

    1. I think you should wear the blue Aidan dress to the party! It looks perfect for your figure, and is by far the most modern. I think a lot of the other dresses look pretty matronly.

  12. Does the long sleeve velvet come in a petite version? I know it wouldn’t make it in time for this party, and I think the Eliza J is the best option for this party anyway. But if you would keep this for future use, try a petite if available. I’m short waisted too and have found when dresses bunch like that one me (often it’s the zipper?) a petite solves the problem. Love that dress tho, it’s gorgeous!

  13. I love the one shoulder dress on you, but I also think the red velvet long-sleeve dress is STUNNING and so flattering on you! The roll in the back is a bit weird, but I’m sure I wouldn’t notice it if you hadn’t pointed it out. With the heels and that feathery bag – what an amazing holiday outfit!

    1. Yeah, it’s weird in person. The 8 is way more comfortable but it’s really too long in the chest and shoulders. The 6 isn’t so bad there but it’s skin tight and also has the weird roll in the back. It’s just too expensive to settle for those imperfections. But I agree, the whole outfit with feather bag and the shoes I can’t walk in (lol) is amazing.

  14. I actually really love the black dress with the faux fur capelet. I don’t think it looks mumsy at all. I think it looks pretty chic.

  15. I really like the bright pink sweater; of course, bright pink is one of the best colors for me to wear. I hope you will tell Paul about the long one button coat for your Christmas. You look fabulous in the black one shoulder dress for the party, but I have to say that the red would have been a contender for you, in my book. I pray that your flights will not be impacted by the various weather systems that are sweeping across the country this weekend.

  16. I love that sweater dress and boots, such a lovely combination and flatters your figure. It reminded me of my younger days when I knitted myself a dress, gosh it took ages to make something I’d probably never have the patience to do now with over 20 balls of wool. I used to wear mine with black knee high leather boots.

  17. Another way to view it… She’s sharing HER opinion of what she’s got on. It’s ok. If she was an employee of a company that required her to have a positive viewpoint about everything- that’s a different scenario. In life, if you’re solid on the choice you’re making do you let outside influence in? I hope not😊 Jo Lynne’s expressions shouldn’t sway you either if you like something. Feel confident about your choices.

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