My Most Worn Winter Wardrobe Staples

As I get ready to transition from winter to spring content here on the blog, I thought I’d write a post about my most worn winter wardrobe staples.

Not too long ago, I did a post on My Must-Have Black Wardrobe Staples. In the comments of that post, or perhaps it was on Facebook, because I can’t seem to find the exact comment, someone suggested that I follow it up with a post about the supporting wardrobe pieces that I integrate with my black pieces to create complete outfits.

I loved the idea, and that got me thinking about what other wardrobe pieces I wear over and over again, which brings me to today’s post!

My Most Worn Winter Wardrobe Staples

These tend to be my investment items because they are pieces I find myself wearing over and over again. I’m willing to spend more on these because they add so much value and versatility to my wardrobe, and the cost per wear averages out to be quite low over time.

These are not trendy, statement pieces… although there is a place for those as well. I find myself wearing more of those in the warmer months, for some reason. In the winter, for whatever reason, I really gravitate to the basics.

1. Pullover Sweaters


Halogen // Old Navy

This will surprise no one. I am unapologetically basic when it comes to my winter uniform — cashmere pullover sweaters and jeans. I like to be comfortable, and I hate fussing with layers, and the easiest thing to throw on is a sweater and jeans.

I try to have a variety of necklines and colors, but most are pullovers, and most are about the same length too — my sweet spot is right around 24″.

I’m not a fan of tunics, as they make throw off my proportions and add visual bulk, making me look bigger than I am; and cropped sweaters just look weird to me. So if they are longer than 25″, I almost always front-tuck them; and if they are shorter than 23″, I usually pass.

When you know your sweet spot length for tops and sweaters, it makes online shopping SO much easier. Most websites offer that measurement, and you will notice when you start to pay attention to the measurements, that sweaters and tops often show differently on the models.

Oddly enough, they usually look longer than they are, even though models tend to be taller than us mere mortals. But anyway, my point is, it’s helpful to figure out your ideal sweater length. And that’s enough about sweaters!

2. Skinny Jeans


Good American // AG Farrah

Sorry, I had to… I mean, if #1 was sweaters, #2 had to be jeans.

If you’ve been hanging out around here for any length of time, you KNOW how much I love my skinny jeans. They just make so much sense in the wintertime because they tuck so neatly into boots, and they also work really well for my body type.

I know some of you can’t wait for skinny jeans to die, while others want to hold onto them for dear life. I’m excited to play around with some other silhouettes this spring, but I don’t see myself getting rid of my skinnies anytime soon. #sorrynotsorry

3. Puffer Coat

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The North Face

I love my wool coats and my shorter quilted coat, but this has been an extremely cold winter here in Philly, and my long The North Face puffer has been worn exponentially more than any other.

I really don’t have much else to say about that! I’m just really glad I invested in this coat during the 2019 #NSale. It’s hard to get excited about dropping a couple hundred bucks on a coat in the middle of summer, but that is definitely the time to do it.

Don’t shoot the messenger, but the 2021 #NSale is just around the corner! You may want to start budgeting now for next fall/winter wardrobe staples.

4. Ankle Boots


Vince // Sorel

In winters past, I wore a lot of tall boots, but for some reason I hardly wore them at all this year. Granted, I didn’t go many places, but I have a pair of casual OTK boots that I wore a TON the last few years, and this year, I don’t think I broke them out even once.

This year, it was all about Sorel winter boots and the Vince Henderson Chelsea boots. I actually ended up with several new pairs of winter boots this year, which is unusual for me. I guess I needed an update.

I wore them a lot, but not as much as the Vince Henderson boots — another #NSale purchase, now that I think about it! It really is worth budgeting for that sale, you guys. SO many of my winter staples were purchased during that sale over the past few years.

5. Joggers


Zella // Vuori

As we all know, 2020 was the year of the jogger, the year of loungewear, the year of life as we know it getting #canceled. I have never worn joggers until last year, and now I am the proud owner of four pairs.

Okay, I’m not exactly proud of it, but I’m not ashamed either.

I actually really like how versatile they are, and how stylish they can look paired with a fitted jacket and a quality t-shirt.

Joggers are going to forever change my travel uniform, if nothing else. When I drove C to Boston for her college visit last fall, I wore a very similar outfit to the one above with the Vuori joggers, and I was so comfy.

I have plenty of jeans that I find very comfortable and easy to wear traveling, but I’ll admit, the joggers are a whole new level of comfort. Yes, please!

6. Fashion Sneakers


P448 // Veja

Even though winter is usually for boots, I found myself wearing sneakers a lot this year… and not just with my joggers, although of course, that is part of the reason. But I also found myself wearing them with a lot of my jeans and sweater outfits.

My skinny jeans and sweaters are all fairly classic styles, and fashion sneakers give them a more modern, cool-girl vibe.

7. Crossbody Bags


R Minkoff // Gucci

I’ve always been a tote girl, or at least a shoulder bag/bucket bag/hobo bag kind of girl. I like to carry a lot of stuff, and I want plenty of room for stashing extra junk when I’m out and about.

In the past, crossbody bags were relegated to date nights and other dressy occasions. Whenever I took one out with me, shopping or wherever, I would always find myself needing something from my bigger bag that I left at home.

Enter Covid.

Actually, in all fairness, I downsized my handbag and purse essentials at the end of 2019 when I got the Gucci Soho Disco for Christmas. It’s more of an everyday crossbody, whereas most of my crossbody bags in the past had been dressier. Of course, it was a big investment, and I started carrying it a lot.

The large wallet that I always loved to carry in my totes and shoulder bags didn’t fit well inside the camera bag, so I found a mid-size wallet that works for me in all my bags. For a while, I switched my bags around a lot and carried the bigger ones sometimes still, but when Covid hit, I started carrying my crossbody everywhere.

It seemed more sanitary because I didn’t have to hold it, or set it in the shopping cart. I also don’t usually go out for long periods of time anymore, and over the past year, I realized that I didn’t need all the crap I was carrying in my bigger bags.

So, as it turns out, 2020 was the year of the jogger AND the crossbody.

And that, as they say, is a wrap! I could go on, but I think this covers the big ones, and I am eager to get a move on here. I plan to post a try-on haul tomorrow, and I still have some pictures I want to take, plus writing those posts always takes AGES.

If you see any issues with the new blog design, please let me know! We are working on ironing out all the kinks.

This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!

photos: Alison Cornell

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46 Responses

  1. Good post. The end of each season is a good tIme to evaluate your wardrobe essentials And replace them since retailers may be reducing prices to make room for the upcoming sEason.

  2. Great post! I’m the OPPOSITE with the handbags thOugh. I used to carry cross body bags a lot, because they weRe so much lighter and hands free. Now thAt i am doinG almost all shopping online and am rarely out for a long period of time, i find myself carrying a larger tote. It has room for extra masks and hand sanitizer!

  3. Love this post! I’m all about the essentials, and thanks for the reminder about the #NSalE. this is the perfect time for me to look At my winter wardrobe and Make a list FoR July. I Find it ImPossible to think about winter clothes In 100* weather! I bought the viori joggers In january 2019 thinking i was wearing On Our trip to france. Well, that Didn’t happen but They’ve been on repeat all fall and winter. Love the new blog look too!

  4. Hi Jo-Lynne, I really like posts like this. Your new blog looks great! You already know about having to write in all caps and about having to look for the comments. I read yesterday’s post this morning and everything looked a-okay. About 4 hours later, I read today’s post and now there is an ad that I cannot get rid of. It is covering about a third of the righthand side of the comment section. I am viewing your blog on a laptop. I thought that I would let you know.

  5. Congrats on the new website! I think once you make a few tweeks it will be pErfect. I noticed that the font seemed lighter and smaller or maybe it was just me getting Use to the new format? Great post but im Ready for some freash spring sytles and would love to Buy that Disco crossbody bag as ive been eyeing it for a year now, just cant justify the price. Does it ever go on sale?

    1. No, I don’t think Gucci goes on sale, but YSL is often included in some of the Saks sales. I was able to get one of my totes on sale. I also have the YSL Lou camera bag, and I like it a lot, although it feels tad dressier than the Gucci. I think it will have more longevity.

  6. Thanks for the heads up/reminder of Nord sale. You’ve talked a lot about investment pieces. I’ve found myself leaning that way this year with many Of my PURCHASES. Sometimes less is more. As others have mentioned, the pop ups bLock the comment section. Mine popped up 3 times while writing this. THere also seems to be more ads than usual.

  7. After reading this its nice to knoe that we share the same stapleS! I Like the new blog lAyout, only a few things: 1) when typing i could not use the line on my iphone that can insert the word you aRe trying to tyPe. 2) when i opened your email to read i had a hard time trying to exit out the block with your Picture to sign up for the daily emails as i am already a suBscribEr. Other than that and having all capitals it seemed fine.

  8. I really enjoyed this post. The website looks nice and clean and no issues at all that I noticed. I do look forward to next week and your spring series!

  9. I like the look of your new site but there is an AD on the right hand side that overlaps your page. I can’t see an X to click on to get rid of it. I read on an ipad. I prefer tHe obvious comment section to this hidden one.

  10. I don’t understand why blogs can’t determine that if you’re alread a subscriber, you don’t need the pop-up. I clicked on my daily email and immediately got the “subscribe” pop-up. just seems obvious but apparently isn’t. and you weren’t kidding about the hidden comments section. i had to really look even to find it.

    love most of your winter choices. i don’t have one real cashmere thing, but maybe i’ll consider it next year. I am able to wear jeans for the first time in my 40 years of working, and this would elevate it some. i actually liked all the choices except the joggers. they just look like sweat pants to me — fine for home but not for out and about if you want to look stylish. but i’m old haha. and there’s no way i could carry a small bag. i try but i just have too much stuff!

    i hope you can get the blog whipped into shape like you want it.

    1. Yeah, it’s annoying. I will probably ditch it. I hate them when I’m on other sites, so why would I do that to you all? 🙂 I just hear they’re very effective and thought it might be worth a try.

  11. Agree with you about cross body purses, joggers and puffer coAt: I wore mine lots. Agree with the other comments about large ad on right side blocking the screen. Its tricky to find the comments section at the bottom…… it was easier to find it at the top before plus showed tHe number of Comments. The geek in me found that interesting 🤣 i use my ipad or Macbook pro or LG phone to view your posts.
    Stay safe and warm!


  13. I commented on facebook YESTERDAY that the website looks great aNd it odes – very clean and fresh. I like the Font. Just as feedback, i’m reading on my iPad so don’t know how it Shows up on a computer but im nOt crazy about how the paragraphs and actual part to read are only on the left 2/3rds of the page. I know there are info boxes at the top but as you scroll, its 2/3rd writing and 1/3 blank. Not a big deal but between that and the ads at the bottom and in the middle, there is a lot of “real ESTATE “ taken up by non blog mAterial.
    Hopefully the cAps aren’t too Wonky here.

  14. I REALLY like YOUR new design. Okay, I did until I found out that the prompts are not working, I GUESS DUE To THE ALL CAps. I rEally lIke today’s post. A lot of the things you mentioned are true for me also.

  15. I love this! My staples were pullover sweaters, skinny jeans and sneakers/sneaker boots as well! Along with my small crossbody bag – I do curbside pick ups, so no big purse needed. This one tucks into my console easily and holds a mask and my drivers license and a credit card. I wonder if I’ll even want or need to go back to a larger purse even when I do start shopping in person again? Oh – and the subscriber box did not show up this time!

  16. I am still trying to figure out the Joggers. I am 5’10” and they just seem to be too short for me. Does anyone make joggers that are for us taller ladies? I would love try on a pair.

  17. Is your Rebecca Minkoff Love crossbody the small Love or the regular? And do you know what the color is called? I’m looking for one on eBay (I don’t think it’s available anymore on the RM site). Thanks!

  18. Good overall choices I think. I wish those gucci bags would go on sale haha. No way this girl could ever afford one. The new website is fine – and yes annoying to search for the comments, but now that I know I have to look for it, I will find it. So onward and upward.

  19. Very nice job on the new site. First, I totally agree…… make the comment section where you can see it without searching and that you don’t have to click a link. 2 nd the pop up to subscribe is annoying but if it’s going away later than we all can be patient.:) I’m sure it may help others subscribe, but wouldn’t new comers subscribe later toward the end of blog after they’ve read it and looked around? Looks like a lot of work you’ve put in to make it so nice. Lots to look at and search. Fun. I like your post today. Do you wear your Live Inn Zella joggers much? You seem to grab the others? I bought them and they do seem a little high waisted. Do you find that? So comfy though. I had a old pair for years almost the same when they first were out. They since have worn out and look too big. I need to invest in another pair to have two. Can you still keep eye out for cute ones for Spring? I might need to buy the vuori ones. 🙂 Hope you are still enjoying your snow. Ours came and went too fast here in Oregon and I wanted it so bad. I love to get it in the Winter but not after Feb. 🙂

  20. PS. Hey… just started to read others comments after I just commented and I’m on my 10XR IPhone and the comments I’m reading don’t fit all into the screen. I have to scroll to right to catch end of sentences. Also as I’m typing this it’s moving left to write as I type. Is this how you wanted it? So when I go back to proof read my comment before sending, I have to scroll left to write to do it. Hope this all makes sense.

  21. Nice design. Took me a minute to find the “leave a comment” section but obviously i found it 🙂 – I am reading on a desktop too.

  22. The pop up makes it impossible for me to read your posts on my iPad because the X is not accessible, so the pop up just obscures the post. I can get rid of it on my iPhone but my iPad.

    1. Hey Sharel, I am hearing this, and I am so sorry. I am waiting for my developer to get back in office, and I will have him take it off. More trouble than it’s worth. Meanwhile, I’m going to poke around on my end and see if I can figure out how to get rid of it.

  23. Hi Jolynne,

    I love your blog. I was wondering if you could do a post sometime on “quality T-shirts.” I have trouble finding good ones.


  24. LOVE the new blog look and color PALETTE! Can you share the brand/style of the jeans YOU’RE wearing in the photo of the Vince boots? I like the way they work with the booties. Thanks!

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