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Winter Try-On Session – Skirts, Grey and White Denim, Dresses

January 14, 2022

Happy Friday! I recently ordered some skirts and dresses from Ann Taylor, and I’d like to share that order with you today. I’m also throwing in a few other random pieces I’ve received from Nordstrom, J.Crew and Talbots. And of course I’ll be trying these garments on with other things from my closet, several of them still available. Let’s get started on this winter try-on session!

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Winter Skirts Dresses and More


I weigh about 155 on a good day and I’m holding steady so far at 5’8″ tall. I have a pear or hourglass shape and balanced proportions. That’s just to give you reference when you’re looking to see how these items fit on me.

I generally wear size 8 in tops, bottoms and dresses. But at I sometimes wear the curvy fit size 8 if they are available. I generally wear a medium in all of those pieces, too. I wear a size 9.5 shoe almost without fail. So unless I tell you otherwise, those are the sizes I’m wearing.

SALE ALERT: Ann Taylor is offering 40% off today with code FRESHSTART. Many of the items I’m showing are from Ann Taylor.


Chain Print Midi Slip Skirt

This midi slip skirt is fully lined and fits nicely true to size. Like all skirts cut on the bias, it feels a little odd when you first put it on. A little crooked, if you know what I mean. But I quickly adjust to it. I actually wore this outfit Wednesday night when we went out to dinner for our anniversary, and we took photos that I’ll share next week. But the skirt is selling out, so I wanted to share it with you now.

Chain Print Midi Slip Skirt // Cropped Cashmere Cardigan // similar boots (mine are no longer available) // earrings // comparable necklace

The main thing I like about this midi slip skirt is that I think it will be in my closet year round. It’s light enough to wear in spring and summer. I think it looks best with a cropped length top, like the Cropped Cashmere Cardigan from Everlane that I’m wearing. But, depending on your body proportions and shape, you could wear it with a longer sweater or top, too. The midi slip skirt has an elasticized waist band and simply pull it on. but it has a flat, finished appearance.

Verdict: Keeping. I really enjoyed wearing this skirt out to dinner Wednesday evening.

Plaid Houndstooth Midi Slip Skirt

Other than the fabric being a little silkier and obviously a different pattern and color, this Plaid Houndstooth Midi Slip Skirt is really just like the above midi slip skirt. It fits nicely true to size and has that same flirty flounce at the end. It also features the elasticized waistband with the finished, flat appearance. So you could wear tops tucked in if you’d prefer.

Winter Try-On Skirts 2
Plaid Houndstooth Midi Slip Skirt // Cropped Cashmere Cardigan // similar boots (mine are no longer available) // earrings // comparable necklace

I still prefer this skirt with the cropped length sweater, too. But you could also wear it with something longer if you’d like. I showed it above with both boots and pumps. It might be fun to wear this midi skirt with a t-shirt, denim jacket and sneakers in the spring or summer, too.

Verdict: Returning, only because I don’t want to keep both. But I love this skirt. It was a hard choice.

By the way, the Cropped Cashmere Cardigan is from my closet, but it is still available in most all sizes. And it also comes in an oatmeal color and what appears to be a dusky mauve. I wear a low cut camisole underneath, and the buttons stay fastened nicely for me.

Floral Pleated Midi Skirt

Pleated skirts have been trending for a couple of years now, and fashion reports indicate that they’re going to get even hotter. So I decided it was time to try one. I think the key, especially for those of us who are not pencil thin, is to select a skirt with enough weight to it so that it hangs nicely. This Floral Pleated Midi Skirt checks that box.

Winter Try-On Skirts 3
Floral Pleated Midi Skirt // Cropped Cashmere Cardigan // pumps no longer available // cashmere sweater in almond heather (45% off) // Stella Knot Suede Loafers // earrings // comparable necklace

This 100% polyester skirt features a true elasticized waistband. While they do show the top tucked in on the website, I think that’s mainly to show the waistband. I probably wouldn’t wear it that way because that horizontal line will definitely emphasize the waist, and mine is not that small. So you could wear a cropped length top like my Cropped Cashmere Cardigan or you could do a little tuck, as I did on the right. But you can also wear a longer length sweater or top here, too. The proportions will just be different.

I’ll absolutely wear this Floral Pleated Midi Skirt with my black boots as well as my camel colored suede boots. But I showed it here with pumps and loafers, just so you could see some other footwear options. And yes, you absolutely can wear hose if you’d prefer (I probably would!). Just choose some that are very sheer and nude (your shade of nude).

Winter Try-On Skirts 4
Floral Pleated Midi Skirt // cashmere sweater in almond heather (45% off) // similar boots or these // earrings // comparable necklace

This Floral Pleated Midi Skirt features black, camel, ivory and a little bit of blue. I tried it with a blue sweater and didn’t especially like the results. But you could certainly give it a try. I was a little impatient with the process. But I love it with black. I just thought you might like to see the camel options.

By the way, I apologize that my black suede boots are no longer available. I purchased all of these skirts and dresses specifically to wear with those black suede boots. But then they quickly sold out. Ha! I’m linking to a few option for those and my camel boots (several years old) in the shopping widget at the bottom of the post. Keep in mind, it’s late in the season and sizes are picked over. They’ll go fast, too.

Verdict: Keeping. I like the accordion pleats a lot more than I thought I would and I definitely want to work with styling it throughout the year. So expect to see me style this skirt and the blue one above several ways through spring and summer. They’ll be sold out, but you can apply the same principles to other similar slip skirts and accordion pleat skirts. Both are very on trend.

Cashmere Blend Tube Skirt

I had very low expectations for this Cashmere Blend Tube Skirt because I tried several during the Nordstrom Anniversary Sale with no luck. But I think the very soft, stretchy cashmere blend fabric is the deal changer here. Yes, it is still body forming, but not body hugging. I am wearing light hold shapewear underneath.

This Cashmere Blend Tube Skirt is a Nordstrom find. And it’s pricey. But since it does indeed fit beautifully and wear nicely, I think I’ll get a lot of wear out of it. (I really didn’t think I’d be keeping this skirt when I ordered it!) It also comes in a tan portabella heather, and I think it would be absolutely lovely. The only thing preventing me from ordering it is the price.

Winter Try-On Skirts 5
Cashmere Blend Tube Skirt // grey shrunken cashmere cardigan // cashmere sweater in almond heather (45% off) // similar boots or these // earrings

Again, you can see that I’ve styled this skirt with a cropped length cardigan and another fairly short length sweater. But you could probably wear it with something more tunic length, too, especially in black. I think I also prefer it with my black boots or heels, but showed it here with snakeskin grey pumps and my tan suede boots. I’m wearing a size medium in the skirt.

Verdict: Keeping. I look forward to playing around with different ways to wear this skirt, too.


Midi Flare Sweater Dress

I hesitated to order this Midi Flare Sweater Dress because the color appeared somewhat purple on the website. Indeed, it is more dark violet than blue. In fact, it’s called “rich ultraviolet.” And when it arrived I still wasn’t sold on the color, but I decided to let it hang in my office and see if it would grow on me.

Winter Try-On Dresses 1
Midi Flare Sweater Dress // similar boots or these // earrings

Well, it did. Mainly because I love the dress itself. The polyester, viscose, nylon blend knit is very, very soft and has a lovely drape. So without a belt or anything, the dress just hugs the body perfectly and then falls so nicely from the waist. The dress is not tight at all, but just fits really nicely and true to size. It’s not lined, of course. I’m not wearing a slip here, but I will when I wear it. I’ll wear this slip because it works so well with form fitting dresses like this.

Verdict: Keeping. I wanted to wear it to church last Sunday, but we had rain in the forecast (and I wanted to wear my suede boots). And there’s snow in our forecast this Sunday. But eventually I will wear this beautiful dress!

Floral Collared Belted Shirtdress

I thought this Floral Collared Belted Shirtdress might be fun to wear with boots now and then with lighter footwear in the spring. It’s 100% lyocell, so it’s a smooth fabric that is a little richer than the cotton I might appear to be. It has a nice drape, too. I did steam it, but I probably would need to iron it for a better flow. (I just don’t iron garments unless I know I’m going to keep them.)

Winter Try-On Dresses 2
Floral Collared Belted Shirtdress // similar boots (mine are no longer available) // earrings // comparable necklace

I do think the print is so cheerful and lovely. The colors look very modern and vibrant. The dress fits nicely true to size and feels great on. Again, I would wear a slip with it. It doesn’t button up the front, as you might would expect. Or at least, I thought it did. But it just has a split collar and you pop the dress on over your head (easily).

Verdict: Returning. But only because I decided I just don’t need it for my lifestyle. If I worked outside my home office and had more occasions to wear a work appropriate dress, I’d definitely keep it.

Denim & Blouses & Sweaters

White Jegging Jeans

I actually have ordered two pair of white jeans from Talbots, but the high waist straight leg jeans are delayed in shipping. These are the White Jeggings in the curvy fit. They also come in a regular fit, of course, but I’m very glad I went with the curvies. It’s worth noting that Talbots seems to have adapted their jeggings with the times. They are no longer as “jegging-like” as they once were. These simply skim the legs rather than hugging them. And I love that.

Winter Try-On White Jeans Grey Sweater
White Jegging Jeans (in curvy fit – here in regular fit) // wool and cashmere half zip sweater // Stella Knot Suede Loafers // earrings // comparable necklace

I really like the feel, the length and the fit of these White Jeggings. They have a nice high rise. Talbots never provides that information in inches, but I measured for myself and my misses 8 has an 11″ rise. They have a bit of stretch in them for comfort, but do not stretch out significantly with wear (any jean will stretch out some with wear). I wore these a good bit Saturday for videos.

Verdict: Keeping. I think these will be my go-to jeans for spring and summer. But I have a video coming up with ideas for styling them for winter, too.

I’m also showing the Vince wool and cashmere half zip sweater I recently ordered from Nordstrom. It’s still pricey, but this half zip sweater is 40% off and still available in a lot of sizes in this soft grey, a beautiful soft desert clay and black. I really wanted the soft desert clay, but convinced myself to buy the grey instead. I may swap. It has a huge collar on it, but I think that’s pretty on trend. It does create somewhat of a masculine look, so if that’s not your bag be forewarned. Otherwise, I love the tapered yet relaxed fit. It’s a hefty sweater, too.

Verdict: Undecided.

Animal print Chesterfield coat

Winter Try-On White Jeans Grey Sweater Coat
White Jegging Jeans (in curvy fit – here in regular fit) // grey shrunken cashmere cardigan // steel grey suede booties (TTS) // animal print Chesterfield coat // earrings // comparable necklace

Above I’m showing those same White Jeggings with the Animal print Chesterfield coat from Ann Taylor. I purchased this coat to show with the white jeans. I think if you want to wear white jeans in the winter (and you absolutely may!), then you do need the right accessories and outerwear to make them look appropriate. But I don’t really like to wear white jeans in winter myself. That’s just a personal choice, not a rule.

But back to the coat! Yes, I do love this animal print Chesterfield coat. It’s roomy enough at my true size medium to wear with bulky sweaters underneath. It’s a nice thickness and buttons up beautifully. This is a true coat, not just a fashion piece that looks like a coat. Know what I mean? It would truly keep you warm.

Winter Try-On White Jeans Grey Sweater Coat 2
White Jegging Jeans (in curvy fit – here in regular fit) // grey shrunken cashmere cardigan // steel grey suede booties (TTS) // animal print Chesterfield coat // earrings // comparable necklace

Verdict: Undecided. I love the coat. But since I don’t wear a lot of white in the winter I’m not sure it’s a wise investment for me. If I did wear white jeans, I’d snap it up for sure.

I’m also wearing another purchase from Ann Taylor here, my steel grey suede booties. These booties feature a 3 1/4″ heel, so I know some of my readers will not care for that. But I wore these to lunch and a little shopping yesterday with no problem at all. I feel no worse for the wear today. And I think the grey shade is a nice addition to a wardrobe that is heavy in grey or even navy.

Verdict: Keeping. I like the narrow, high shaft for fitting them under slim fitting jeans. And they feel great true to size. I’ll wear them with grey and navy for sure.

Sculpting Pocket Mid Rise Taper Jeans in Natural

When I was looking for white jeans, I discovered these natural colored Mid Rise Taper Jeans and thought I’d give them a try. I think for a different body type they may work well. But the mid rise just doesn’t work for me. I really prefer a high rise jean or pant at this point. With my balanced proportions and hourglass shape, that silhouette just fits me so much better. The mid rise hits me very uncomfortably and sort of pulls at the crotch. Maybe that’s because I try to pull them up and make them be high rise. Ha!

Winter Try-On Ivory straight jeans 1
Sculpting Pocket Mid Rise Taper Jeans in Natural // floral essential shirt // steel grey suede booties (TTS) // earrings // comparable necklace

Plus this length of pant is just not what I want for winter. I know some women continue to wear the cropped length jeans during the winter, but I just prefer full length. So I don’t really know why I ordered them??? Anyhow, the natural color is nice and the fabric is great. So there’s that. And they seem to fit true to size…if they fit. But they just don’t fit my body.

Verdict: Returning. They’re nicely made jeans, but just not for my body.

floral essential shirt

I’m wearing the with Mid Rise Taper Jeans with the floral essential shirt, also from Ann Taylor. In fact, you may recognize the print from the dress above. But this floral essential shirt is made from a different fabric. It’s lighter weight and 100% polyester. It’s going fast, too. Again, I think this color and print is vibrant and a fun pick-me-up for winter.

Winter Try-On Ivory straight jeans 2
Sculpting Pocket Mid Rise Taper Jeans in Natural // floral essential shirt // steel grey suede booties (TTS) // earrings // comparable necklace

Verdict: I’m keeping the floral essential shirt. I wore it yesterday with blue jeans and my black leather blazer, and I really enjoyed wearing a blouse for once. By the way, I sometimes struggle with blouses because my upper arms are a little large and many blouses are too tight on me there. But this one fits. It’s not loose, mind you. But it fits comfortably in the arms.

Winter Try-On dark wash straight jeans blazer
straight leg jeans (I cut them off) (curvy fit) (plus size) // floral essential shirt // steel grey suede booties (TTS) // earrings // comparable necklace // similar blazer // leather belt (wearing medium)

And here’s a peak at yesterday’s outfit without the jacket.

Winter Try-On dark wash straight jeans 1
straight leg jeans (I cut them off) (curvy fit) (plus size) // floral essential shirt // steel grey suede booties (TTS) // earrings // comparable necklace // leather belt (wearing medium)

Okay, back to blouses and ivory jeans.

High Rise Boot Cut Jeans in Ecru

I thought I’d also try out the High Rise Boot Cut Jeans in Ecru from Ann Taylor. I could tell these were longer and I liked the fact that they are high rise. Sure enough, they do fit and feel better. Oh, and I’m also wearing the curvy fit. BUT, I’m not a big fan of bootcut on me unless they are longer. Right now shorter bootcut silhouettes are trending. But I just haven’t gotten on board yet.

Winter Try-On Ivory boot cut jeans
Floral Tie Neck Raglan Sleeve Top // High Rise Boot Cut Jeans in Ecru // steel grey suede booties (TTS) // earrings // comparable necklace

So these High Rise Boot Cut Jeans in Ecru are really great jeans, but they’re just not for me. If you love or are looking for something similar, I can tell you that they run true to size. And I definitely appreciate the higher rise. You might want to size up for a looser fit, if that’s something you enjoy. These feel snug on me, but if I sized up I fear they would look too roomy.

Verdict: Returning.

Floral Tie Neck Raglan Sleeve Top

If you’ve watched yesterday’s video you saw me wearing this Floral Tie Neck Raglan Sleeve Top. It’s soft and features fuller sleeves with a bell shape at the bottom. You can tie the neck tie or leave it open, as I did in the video.

Floral Tie Neck Raglan Sleeve Top // High Rise Boot Cut Jeans in Ecru // steel grey suede booties (TTS) // earrings // comparable necklace

The raglan sleeve top is 100% and machine washable. It’s a nice print for wearing with blue denim, too. A great way to add a little color and cheer to a winter wardrobe.

Verdict: Keeping.

Slim ankle jeans in stratus wash

I also purchased the Slim ankle jeans in stratus wash from Talbots. Now these I love. I really like the idea of grey jeans year round. While I prefer to pull out my white jeans fresh each spring and summer, grey jeans work for me all year. These Slim ankle jeans in stratus wash are a mid rise, measuring at 10″ on my misses 8s. They have comfortable stretch and feel great on.

Slim ankle jeans in stratus wash // floral essential shirt // steel grey suede booties (TTS) // earrings // comparable necklace // wool and cashmere half zip sweater

The Slim ankle jeans in stratus wash have a straight leg, skimming the body. But they really read a lot like the white jeggings above, other than that 1″ lower rise.

Verdict: Keeping. I’ll be featuring these in an upcoming video on wearing grey in winter.

J.Crew Cashmere cable-knit relaxed v-neck sweater

This cable-knit relaxed v-neck sweater is marked down and you get an extra 50% off with code EPIC. But it is final sale. I’m wearing the medium and it’s a roomy fit, but I think that’s by design. If you want a slimmer fit, I think you could easily size down. It is very comfortable and super soft.

J.Crew Cashmere cable-knit relaxed v-neck sweater // straight leg jeans (I cut them off) (curvy fit) (plus size) // earrings // comparable necklace // Stella Knot Suede Loafers

On the negative side, the cable-knit relaxed v-neck sweater is a little thin. I usually wear a camisole under it, but didn’t bother to put one on for this try one session, and you can see that it’s a bit sheer (see my blue jeans showing through?). But with the camisole, it does fine. The cable-knit relaxed v-neck sweater comes in a few other colors, too.

Verdict: Keeping. I’ve already worn this sweater a bit and enjoyed it.

Stella Knot Suede Loafers

I’ve shown the Stella Knot Suede Loafers a few times above, so let me fill you in on those, too. I purchased those mainly to wear this spring. I like the idea of wearing suede in softer colors in the spring because those are still cool days here where I live. And I think they look great with white, too. However, the Stella Knot Suede Loafers do fit a little loose. I’m keeping them and I’ve worn them a bit. They stay on with no problem, but they just definitely fit me looser than Talbots flats usually do. So just keep that in mind.

Alrighty! That’s a wrap. Let me know if you have any questions. I’ll try to keep a watch on the comments and get back with you asap. Also I’ve filled two shopping widgets below with items in today’s post plus other similar items that I like.

SALE Alerts!

Ann Taylor is offering 40% off with code FRESHSTART. That includes a lot of items in today’s post. Also at Talbots is wrapping up their Red Hanger Sale with 50% off all markdowns PLUS an extra 20% off. You’ll also enjoy an extra 5% off if you use your Talbots credit card. AND Talbots will give you 30% off one full price item (difference shown in bag) this weekend only. That’s the most they’ve offered off this newest line.

J.Crew is offering an extra 50% off markdowns with code EPIC (exemptions apply). And I think all or almost all of the items I showed from Nordstrom are marked down. But don’t forget that the Zella activewear I featured earlier this week is 20% off (or more) just through Monday (and selling fast!).

Shop the Post:

You can shop the look through the links in the copy above or through the shopping widget below. Sale prices are not always reflected in the widget, so click through to get pricing info. Remember, if you purchase anything through these links I potentially earn a commission, but at no cost to you. Thank you for shopping through Dressed for My Day. I am grateful!

And here’s the widget that contains Talbots’ fashions:

Don’t Miss a Post:

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Blessed for My Day

Some days the circumstances of life can cloud our vision and prevent us from seeing beyond the hard things we are going through. Those are the days when we must doggedly choose to believe what we cannot see but know to be true. One way we can clear our vision a bit is to recall what God has done for us in the past as well as who we know Him to be.

Why not spend a few minutes right now remembering the way God has brought you through hard seasons before? Recall how He worked even when you did not yet know He was working. Remember the way He never left your side but was always near…even if you could not feel His presence at the time. And recollect how He not only answered your prayers but also tended to the groaning of your heart.

I will remember the deeds of the Lord;
    yes, I will remember your miracles of long ago.
I will consider all your works
    and meditate on all your mighty deeds.” ~ Psalm 77:11-12

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xoxo, Kay
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22 thoughts on “Winter Try-On Session – Skirts, Grey and White Denim, Dresses

  1. Hi Kay! That blue/purple dress is stunning. Plus you look great in it. I have no use for a dress right now or I’d be tempted to order it.

  2. I like all of your looks today. I especially like the chain skirt, black boots, and black sweater as well as the blue dress. Interesting slip thanks for including the slip. My daughter lives in southern OH on the Ohio River and she is preparing for the storm. I hope it is not bad in Cincinnati. Have a blessed day.

  3. My favourite item is the Animal print Chesterfield coat, which looks very slimming and modern. It really suits you. I don’t tend to wear white jeans in winter either, but perhaps it could be worn with pale grey jeans, which I think is the background colour? It looks so good on you it’s a pity to send it back, lol!

  4. I have gray as a base from charcoal to very pretty pearl grey. I love 1/2 zip sweaters and this looks wonderful with the gray pants and black boots. But….I’m just not sure I like that much collar. It looks like it might take effort to put a jacket on over it. I like the blue and black/white skirt but no pleats for me. Pink and navy blouse is a winner. Love that outfit! WHEW!

  5. I think the blue dress looks fabulous on you, too! I don’t wear my white jeans in the winter, either, but for those who do, I really like that animal print coat!

  6. I absolutely LOVE all the skirts!! The dresses are nice except I’m not fond of the pink patterned one. You did a great job!!

  7. Kay, I loved your video yesterday. Getting older is not fun but you put a positive spin on it which I really need.
    In todays post I loved all the skirts paired with boots . They looked more modern and regal that way.

  8. I don’t usually remark but I was not impressed with the clothing shown today. The skirts and dresses were just a no and all the florals just looked frumpy. The tans and pale greys do not look right with your light hair and coloring. These colors do not do your beauty justice. Sorry but just my opinion!

    1. Interesting. Kay, I appreciate that you recognise that we are not all fair with your proportions, style and taste. Thank you for showing such a variety of options that are available in store and discussing your thoughts and verdict on each piece. We are mature women who can follow suit. My take home message is that I wouldn’t wear the pink floral print in a dress but it is appealing as a blouse with dark jeans. I am so keen to incorporate skirts into my wardrobe this year and you highlighting the different shoe choices and ways of styling the skirts has made me see how I would choose to do it. Always good to keep an open mind. If you only ever wear what suits you, only your clones could subscribe .Thank goodness we don’t all hit the streets wearing the same clothes!

  9. I want to share how God has helped me. I am 5’8”, like you, though I’m 65… a few years older. In September I was a solid size 14 and many more pounds than I should be. I made changes. As of today, January, 14, I am 155 and a size 8. I ‘m not saying everyone should be that size or proportions, but I wasn’t happy and I want to lose a few more pounds. However, I asked God to help me and he did. I feel it is important to thank Him. No fad diet just day by day faithfulness both ways. He never fails.

    1. That is wonderful, Chris. Thanks so much for sharing. And congratulations on your success. I know that was hard work. I’m so happy for you. ?

  10. I loved the skirts and dresses that you shared, They are cost prohibitive for me. Could you share something for those on a lower budget sometime? I get lots of ideas from your videos but can rarely afford anything. Thank you for your consideration.

  11. Great haul. You got a lot of cute things and I agreed with most of your keep/return decisions; however, I wish you had kept the pink dress. I thought it looked FABULOUS on you and you could have worn it a lot this spring and summer.

  12. Rarely comment, but this was a fabulous post–lots of great looks in something besides jeans. By the way, you look like “a million” in that ultraviolet midi flare sweater dress!

  13. I agree with many others who said how stunning you look in that ultraviolet midi flare sweater dress.
    I assume Jeggins will fit into calf high boots like skinny jeans. Can you confirm?