My Daily Looks {Holiday Edition}

Happy 2020, friends!!! I share my daily outfits every other week Wednesday, and today’s the day.

I decided to take a break from year-end recaps and waxing eloquent over a new decade, and I’m kicking off the new year with an old-school What I Wore Wednesday post.

This post recaps most of my holiday outfits from the season.

Links to outfit details are beneath each picture, and the pictures are also clickable.

My Daily Looks {Holiday Edition}

First up, an outfit I wore out with friends to a local distillery on a Friday night a couple weeks ago.

Wearing a cardigan buttoned up is very “of the moment”, and I like how it basically simulates a v-neck top, which is particularly flattering on those of us with wide shoulders and larger chests.

This one is from Everlane, one of my favorite companies to support because of their transparency and ethical fashion, and I really like the attention to detail in the knit. It also comes in 4 other colors, and I sized up to a medium.

Also, these grey jeans have been on constant repeat since I got them, but I also linked up a less expensive pair as an option. The mules are old, so I linked similar.


I wore this next look on a Saturday to run errands with the girls. This is my go-to casual outfit formula for when I don’t want to wear a coat.

This vest is from last year, and I love the faux layer look, but it sold out. This one is by the same designer, and it comes in burgundy or black. (I have it in black, and it’s TTS; I have a small.)

These boots are waterproof and very comfortable. I wore them last year on a day trip to NYC, and my feet were very happy. They also happen to be 50% off right now!


That night, we went out to dinner with friends. I shared all about this outfit evolution in a post last weekend, but to sum it up, it was a cold night, and I wanted to be warm but look festive.

The sweater has some shimmer to it, so it’s both festive and warm, and the OTK boots add some drama, plus they kept my legs warm. The earrings are the perfect way to take the casual look up a notch. Both the earrings and boots are old, so I linked similar.

Also, the Gucci crossbody was my end-of-year treat yo’ self gift, and I’ve been carrying it pretty much non-stop. I love it, but I’ve linked a similar Tory Burch bag in my ShopStyle looks because it’s more accessible and comparable to the bags I typically feature.


This next look is from the following Sunday. I had a funeral to attend in the afternoon, and I wore this black sweater dress to church so I wouldn’t have to change in between.

The dress is from last year, so I don’t have a link, but these boots are super comfortable and 50% off.


I wore this next outfit the Monday before Christmas to work from home and chauffeur my daughter and her friends around. Pardon the grainy picture; I took it at night, and my phone was in night mode.

This sweater was an #NSale purchase and is no longer available, so I linked a similar one as well as a more budget-friendly option. I said I was putting it away for spring, but we had some unseasonably warm days last week, so I took the opportunity to wear it again.

My Mother skinnies are still on sale, and my Veja sneakers are getting hard to find, but they do have some at Net-A-Porter.


I met some good friends for lunch on Christmas Eve, and it was another mild day so I was able to get away with a leather jacket.

The sweater is front-tucked, but it’s actually a nice length with a contrasting ribbed hem.


That night, we went out for sushi with the family for my daughter’s birthday, and I changed into something a little more festive.

This sweater just came from Naadam — a brand I’ve been wanting to try for a while. It is probably the softest, most luxurious cashmere I’ve ever touched. It’s absolutely gorgeous, and actually not a bad price for the quality.

I mentioned it in my evolution of an outfit post last weekend, and I finally decided to keep it and wear it when we went out to dinner. It does fit snugly, and I sort of wish I’d tried the medium, but I decided to keep the small and wear shapewear, haha!

The shoes are burgundy, but they’re hard to see in this light. I’ve had them for a few years, and I wish they still made them. They’re the perfect 3″ heel height.


And this was Christmas Day! Paul and I made peach bellinis for brunch.


I spent much of the next day working, and I think I had to run out for a few things… I can’t remember.

The sweater was a Christmas gift from my mom, and the earrings were one of my gifts from Paul. In fact, the necklace was a gift from Paul too, but last Christmas.

We’ve discussed the pros and cons of front-tucking sweaters, but this one is a little long for me, and kind of a boxy cut, so I felt like it needed it. The details and quality are really lovely, but I think I need to put myself on a ban from buying anymore grey sweaters for a while! 🙈


Another day, another grey sweater… at least I know what I like! Unfortunately, this one is from last year, and I don’t have an exact link. I found a bunch of other options, though.


And this next look is from last Saturday, when I hosted Paul’s extended family for Christmas dinner and a gift exchange.

Nothing new here, but I did try a few different jeans before deciding on this pair.

Since the sweater is on the shorter side, I need a higher rise, and I really like this dark blue wash with the burgundy sweater. I also tried the grey (as seen above) and black, but decided on these.


I wore this to church on Sunday. Again, nothing you haven’t seen before!


And this sad picture is from Monday. I didn’t do a thing to my hair. 🤷🏻‍♀️

I had to run out for a quick meeting, but otherwise, I was home all day. It was rainy and dreary, and I was glad for my Sorels.


I spent most of yesterday at home working, but I did run out in the afternoon to get my nails done.


Then we went out to dinner as a family, and then over to a friend’s house for a New Year’s Eve party. Once again, I tried on a few outfits.

I didn’t want to do another outfit evolution post for this, since it will kind of be irrelevant after the holidays, but I’ll share my options here.

Jeans and pumps was a given, but I was debating about my top. The choice of top would dictate which jeans and pumps I would wear.

I purchased this rib metallic sweater with NYE in mind, but I just wore it two weeks ago with the same group of people.

Of course, they don’t care, but I kind of wanted something different. I feel like every time I dress up lately, I go with the light neutrals.

The light grey Naadam sweater from Christmas Eve was another option, and I even considered the new one from my mom since it’s a casual gathering, but I also have a black shimmer pearl cuff sweater from last New Year’s Eve.

I actually went shopping with a friend that day, and bought it for the party I was hosting that night. It’s dressier than my other options, has a super flattering v-neck in front and back, and I haven’t done much black lately. I was thinking about wearing that with black jeans and black pumps for a chic all-black look.

But I was also debating this sequin cowl neck top. I love it and never had a chance to wear it, and it pretty much screams New Year’s Eve!

I tried it first with grey jeans, thinking the monochromatic look could be fun, and the casual jeans would tone down the dressy top, but I don’t like this combination. The jeans are too casual, and I just wasn’t feeling it.

So I swapped out the grey jeans for black coated jeans. This a great outfit, but I knew I’d feel overdressed — both at the restaurant, and at my friend’s house.

I could have gotten away with it if I really wanted to wear it. I mean, it’s New Year’s Eve, after all! But, I also was feeling self-conscious about how pale I am, and I wanted to try that shimmery black sweater before making up my mind.

So here’s the look with the black sweater…

It was exactly as I had envisioned it, and I was thrilled the sweater still fit. (I wasn’t sure how I’d feel in it since putting on a few pounds over the past year.)

Here’s a back view… the back of the neckline is really pretty too.

Plus I always make sure to check my rear view… sometimes you notice things that can be a deal breaker.

Also, you might have noticed these Marc Fisher pumps are new. I recently ordered them in the black suede because most of my pumps have a 3.75″ or 4″ heel, and my feet are starting to rebel. Ain’t aging fun?

These have a 3″ block heel, which is stable and good for walking, but the pointy toe is flattering and keeps them dressy.

So, this was my final look, with accessories and everything…

I wore the pave drop earrings from LOFT Outlet and a layered necklace from the Something Navy line at Nordstrom.

I debated toning it down with plain black jeans, but then I decided to own it and go with the coated denim, and I’m glad I did.

While I was still more dressed up than anyone else at the party, I felt comfortable and confident.

I wanted to wear something festive and fun and a little extra special, and I think this was the perfect compromise.


And that’s a wrap! Not only for this post, but for all of 2019.

I’ll still be doing a few more posts looking back on the year, but I’m also really excited to move forward with some new content. Stay tuned!!!

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13 Responses

  1. You look very nice in the outfit you wore last night!  I sure hope that David feels better soon, and that you can have some true downtime so that you can rid of it real fast.  Our moms always taught us to share, but there are some things we really should keep to ourselves.  Welcome to 2020!

  2. You look stylish as always! Love your NYE outfit. Happy New Year! I too have caught a cold…. Ugh……its like your body knows its downtime. May I suggest getting some sinutab – type of decongestants. It really helps at bed time when flat and stuffed up. Hope you feel better soon!

  3. I hope it’s just a little cold. I start on Zinc tablets when I first catch one. Feel better soon and thanks for helping me be more of a fashionista than I ever would have! Happy New Year Jo-Lynne!

    PS I’m 51 and my feet are quite rebellious as well…

  4. Always such a fun post!  Your final choice for your NYE outfit is perfect!  Glad you stuck with those coated jeans!  Sort of a strange question, but on days you’re at home working –  shoes or no shoes?  Do you wear something like a slipper?  Just wondering! As for me, I’m not sure if it’s good or bad, but I’m a barefoot type of gal. I’ll throw on slipper socks w/grippers if my feet get cold or my LL Bean Daybreak Scuffs, but I’m usually barefoot!  Happy 2020!  Looking forward to seeing what you have in store for us!  

  5. Great outfits! Thanks for sharing so many great ideas. All of these outfits are so my style!

    I have a question: I have metallic (pewter) Naturalizer pumps in my online basket with every intention to purchase. I recently lost a significant amount of weight and one of the many benefits is that some heels are not killing my feet anymore! So I want to rock them! But I can’t visualize an outfit. My style of fashion is similar to your’s – casual and comfortable, yet I like to think put-together. Do you have any jean outfits with metallic pumps that aren’t overly dressy in your archives you can share?


  6. Hi, great post, Jo-Lynne! I like when you share your back-story thoughts on outfits, and what works and what doesn’t.

    As to the cold, have you ever tried a Cold Buster from Starbucks? It’s an off-menu drink made from hot lemonade, mint tea, peach ginger tea, and organic honey. I order the Venti size every time I feel under the weather, via the drive-through so I don’t share my cold.

  7. Hope next Tuesday you are going to start the LIVE back up.  I like them.  Looking forward to 2020 and what you have to come. Happy New Year.  

  8. Darn those Blondo boots have a narrow shaft! They are the right price and almost flat AND waterproof suede! The tragedy of the 15″ calf continues….

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