Style Bee - Winter Closet Assessment

Winter Wardrobe Assessment


Today it’s time to talk Winter Wardrobe Assessment! With Spring previews and sneak peeks everywhere it’s easy to ignore the fact that we still have some time left with this season (no matter what a silly rodent has to say). So before we get ahead of ourselves it’s important to embrace the now, so to speak, and make sure the closet we’re working with is working for us.

I’ve been doing these ‘assessments’ informally for many seasons now and I always find Winter the hardest to face. Unlike Spring, Summer and Fall, Winter in Ontario is long, unpredictable and downright brutal at times. Having a functional closet that I also love wearing was a relatively foreign concept until I started paying more attention to my lifestyle and the items that really work for me. The good news is, it’s really easy to do and will absolutely make a difference for both this Winter and next.

A Winter Wardrobe Assessment goes like this:


  • What do I wear and feel comfortable in most often? 
  • What has spent the most time on the shelf or hanger?


  • What have been my favourite looks to wear?
  • Which outfits do I already plan to repeat this season and next year?


  • While you’re still living in the season make a note of some items you know would integrate well and enhance your closet. This way, when you’re ready to shop for Winter again you won’t be as blinded by the ‘newness’ of things and will shop for items that will really be of use.

To give you an example of how it all looks, I’m sharing my Winter Wardrobe Assessment below. So let’s see!

Style Bee - Winter Closet Assessment


I like to start my assessment with a general inventory of what I’ve been wearing most. To do this I simply pull out (or jot down) the pieces that immediately jump out in my mind as favourites. These are items I’ve worn at least 8+ times so far this season. This is usually a super quick step since they’re either already on my clothes rack or on the edge of my closet shelves.

Then I take a moment to consider any surprises. This time around I was surprised by just how many items I really wear on a regular basis. This indicates that my closet is working well and that the items are versatile interchangeable and very wearable, HOORAY! Another reason why so many items have been used is because of our varied weather this year. For most of January it was very mild so I got to play with some lighter layers and didn’t have to worry about super cold temps and snow the entire time.

Count them up. It’s a good idea to count how many pieces you really wear often in a season. This is an indicator for how well your options are working and how lean a selection you might be able to get away with.

This Winter I have 31 Items in my regular use inventory. I didn’t plan on having a specific number and I wasn’t deliberately trying to include or exclude anything. I just made a list of all the pieces I’ve enjoyed wearing regularly over the last couple of months and that was the number! This includes accessories too but not loungewear, gym clothes or jewelry.

What items have stayed on the shelf? Now it’s time to note the pieces you don’t turn to often and acknowledge that there may be some redundancy or there just might be some pieces that don’t fit your lifestyle all that well. That’s okay! You don’t necessarily have to get rid of them. Instead you might try wearing them to either reinvest or figure out why they weren’t being used in the first place. It’s all about learning what works and what doesn’t, not about what stays or goes.

For me I was surprised to find that my sweater dresses (and dresses in general) haven’t been worn much, my T-Sweater has barely been out and a couple of crew neck sweaters hadn’t been getting a lot of outside time either. The reasons are as follows:

1 – My sweater dresses are dry clean only so I treat them a little like they’re ‘special occasion items’, plus they collect fur easily and the turtleneck on them is very big so I get kind of hot. I might try wearing one to a family dinner this weekend to see how it goes.

As for dresses in general, well, they’re not really applicable to my lifestyle during the Winter. I like to be warm and my activities a relatively casual, so I usually just style up a pair of pants with a cute top and some accessories. I’ll have to keep an eye out at the weather warms up to see if I reach for dresses (like my Georgia Midi, Jersey Swing or Painter Dress) more often.

2 – My T-Sweater is great and I love it but unless I’m wearing a long sleeve tee underneath it’s not warm enough and then the sleeves are so big I can’t wear a coat. So perhaps it’s not the best layering piece for the winter. I might try it again soon with my Capote Coat though!

3 – I’ve become quite fussy about the length of my sweaters. If they’re too long to front tuck in a high-rise pant but not long enough to be a tunic I feel a little off so I don’t wear them much. These might be an indicator of redundancy since I wear my cashmere crews from Everlane all the time. So perhaps I could let one or two of the bench warmers go.

Otherwise all my usual warm weather items from Spring and Summer are waiting patiently for their time to shine. Come on Spring!!!


Style Bee - Winter Closet Assessment




Style Bee - Winter Closet Assessment


I always find it really helpful to make note of my favourite looks and silhouettes so I’m not so tempted to add things just because I can. If it makes sense, great, but when I know I have over a week’s worth of great outfits I can’t wait to wear again, it makes shopping for new things much less tempting!

Remember what your lifestyle really calls for. This was where things always used to go astray for me. I would have lots of cute fantasy Winter looks at the ready, but none of them were actually applicable to my real life so I’d end up in the same uninspired outfit all the time. Now that I’ve come to terms with what I really need and said goodbye to the impractical pieces, I get so much more use out of everything in my closet.

Here’s a look at 8 silhouettes I’ve found really wearable this Winter season.

Style Bee - Winter Closet Assessment

LOOK 1 – Cozy, simple, chic. I love this one so much. The Formula: A slim cashmere sweater tucked into my Kamm pants with knee socks, Pistol Boots, a beanie and my Capote coat.

LOOK 2 – This one proved that I don’t need a parka to be super cozy. The Formula: A slim cashmere sweater over skinny jeans pants with faux fur-lined Chelsea Boots, a beanie, my sweater coat and a wool coat to top it off.

LOOK 3 – This one I discovered in 2015 and have been wearing it since. The Formula: A striped heavy-weight cotton top over skinny jeans with ankle boots, my sweater cape and a big scarf. I just swap the sweater cape for a wool coat when I go outside.

LOOK 4 – Another forever favourite that I love with flares but since the sidewalks have been salty I’ll swap them for skinny jeans. The Formula: I add my cocoon coat to the tunic sweater, skinny jeans and ankle boots, plus with an alpaca knit beanie I feel both toasty and polished.

LOOK 5 – These wool clyde pants have been a game-changer for two winters now. They’re like wearing sweater pants but they’re super warm and totally presentable. The Formula: I love them over a fitted turtleneck with my denim duster and a wide brim hat. I’ll sub in a wool coat and a beanie when it’s blustery.

LOOK 6 – I really hope Everlane keeps making these cropped sweaters because they pair perfectly with high-rise pants and there is nothing better than a fuss free look that just works. The Formula: Cropped crew over a bodysuit with my Kamm Pants, knee socks and chelsea boots, topped with my black coat and a big scarf.

LOOK 7 – This one is my current go-to. The Formula: Fitted turtleneck, tucked into my Kamm Pants, a leather belt, cozy socks, pistol boots, floaty scarf and a black coat topper.

LOOK 8 – I love how this one came together. The palette is so simple and the result was a really functional but still standout look. The Formula: Slim turtleneck, tucked into thick black tights, under a buttoned up oversize cardigan (or a sweater dress like this), with socks pulled up and Pistol Boots.

Style Bee - Winter Closet Assessment


The last step in the process is to establish what you need to improve functionality within your wardrobe. I’ve said it a bunch and I’ll say it again, I swear by my Wish Lists! Creating a short, well considered, practical wish list is probably the most integral step in maintaining a lean, functional closet. Learn a bit more about how to create a useful wish list here and see my previous ones from Spring, Fall (2016) and Winter (2015). 

I’ve mentioned a few times how I like to make them towards the end of a season when my options are fresh in my mind so that I can refer to it the next time I’m ready to shop for that weather. After doing just that, these are a few pieces I’ve got in mind to add for next Winter. I won’t end up getting them all and I’ll probably swap one or two out for something else but it’s really helpful to have this list handy. Then when I’m tempted to buy something impractical for my winter life, I’ll be reminded that it’s probably not a great idea.

Style Bee - Winter Wardrobe Assessment

LONG GREY WOOL COAT – I searched for a long, relaxed fit wool coat in marled grey or herringbone all season. I guess it wasn’t meant to be but it’s #1 on my list for next year! This one was very close to coming home with me but I lost my nerve at the last-minute!

LONG GREY CARDIGANMy sweater cape is great but picks up fur and lint and my cardigan sweater coat is glorious but quite heavy unless I’m wearing a thin tee underneath. This would be the perfect in between that’s cozy and over sized but not too cozy or oversized. Holy Goldilocks syndrome right here!  

TUNIC SWEATERI love love love my Olive Tunic sweater from Elizabeth Suzann two Falls ago. I allllmost bought the Harper Sweater when it was available and now I’m kicking myself for missing my shot. Hopefully they’ll be restocked in plenty of time for next year. I would love to be able to throw this on over a bodysuit or turtleneck with my black jeans or ponte pants and Pistol Boots for a cozy chic outfit.

LONG SLEEVED STRIPESI would love to augment my stripe options with a long-sleeved version. I love the heavyweight cotton of the boxy striped tee so this variation would be a pretty sure hit. Bare wrists are just not conducive to staying toasty at my desk.

WIDE WOOL PANTSo this might be an odd wish list item but I found myself wishing I had a wool version of my Florence pants all winter!

SHEARLING CLOG BOOTI’ve had my eye on these boots for a long time now and after hearing several rave reviews I think I might be ready to invest in a pair. They’d be great pulled on over skinny pants and sleek enough that they’d slip under my wider leg styles too.

BABOUCHE SLIPPEROddly enough a pair of slippers has escaped my clutches for a long time now. It would be nice to add something cute and cozy like these Babouche beauties.

GIU GIU TURTLENECK – These are basically the holy grail of fitted ribbed turtlenecks and I’ve got my heart set on adding one to my roster.

KNEE SOCKSNot a particularly exciting addition to the list but my single pair of knee socks has been in ridiculously high demand. They’ve been my secret weapon for wearing wide-leg pants this winter!

Style Bee - Winter Closet Assessment

So there you have my simple 3-Step Winter Wardrobe Assessment! This approach is applicable to any season and I plan to keep these up throughout the year. 


What pieces have you been getting the most wear out of?

Are you surprised to see any items collecting dust?

What’s on your Wish List for next year?

See something you liked? You can shop it and support Style Bee by using the affiliate links provided. This post is not sponsored but when you shop via the links above I may make a small commission from a sale. Thanks for your support!

Leave me a comment here!

  1. Holly J says:

    Love this post, Lee!

    I’ve been keeping a style journal this season….what am I wearing and not wearing and what am I Welcoming IN (like your wish list!) and what am I LETTING GO of ? It’s just a simple, handwritten journal, but it’s helped me learn a few things.

    Your 10 X 10 helped me ELIMINATE a few items that weren’t working, so thank you. It was the push I needed to take photos…even my poor quality ones…which helped me really reevaluate and reassess.

    My wish list/”welcome in” list included:
    a 2nd hand pair of Frye boots
    a Made in the USA pair of heeled chelsea jodphur boots (Red Wing Harriets…now officially the most expensive thing I own) 😉
    some boot socks (Made in the USA)!

    I love all the different looks you’ve featured with such a minimal wardrobe. Your posts are so well done–the photos, the writing, and the layout. I’m so impressed!

    Holly J

    • Lee the Bee says:

      Thanks so much Holly! I’m so glad to hear the 10×10 was helpful for you and that you’ve found a process that’s working well. I love how you call it a ‘Welcome In’ list! Thanks for reading. xo

  2. CristinaG says:

    Thank you for this great post!?My MVPs this winter have been layering turtlenecks in black, camel, and red, as well as a good pair of burgundy ankle boots. I underestimated how much pleasure I would get out of having my shoes match the color of my coat! Lastly, I added a pair of pinstriped wide leg wool-cashmere pants to my work wardrobe and I can’t tell you how much I love the switch from pencil pants.

  3. Gail says:

    Just became a fan with the recent winter blog along with Caroline. Love how your “voice” comes through your writing as if you’re chatting in person. Your scarf assembling always catches my attention alot! Have you done a past blog about scarf tying that I could learn how you do it? By any chance do you iron your scarves and how do you store them- hanger, drawer, ???

    • Lee the Bee says:

      Thanks so much Gail! I haven’t done a scarf post before but I’ve been thinking it might be fun to do since I wear one all the time! For the most part I keep them neatly folded or rolled in a basket. Thanks for reading! xo

  4. Krystal says:

    After losing some weight and getting rid of a LOT of my wardrobe, I’ve had trouble rebuilding it. I don’t want/need a large amount of clothing, but I’ve struggled trying to find high quality clothes that fit my body at my price point. We live in Florida, but we travel a lot, so I still need some clothes for colder weather. We just booked a trip to Montreal in a few weeks so I’ve got to fast-track a wool coat! I’m on the hunt for a grey or black wool coat nipped in at the waist. I know that oversized and drop-shoulder everything is in style, but it just doesn’t work for my body, and I’m working to accept that (but man, it makes it tough to find clothes!). Other things I’m on the lookout for is a silk cami as the weather warms and some mid-heel boots.

  5. Elyse says:

    Love this, Lee! This kind of intentful assessment is what helped me when I was first getting started and it’s what I fall back to doing every time I find myself wanting to shop. As I am sure y’all have seen from Carolina, Texas winter weather is all over the place. It’ll be 80 one day, and rainy and 45 the next. It doesn’t really snow, or heavy rain much, and while it’s typically windy at least here in town thankfully we don’t require such hardcore winter gear as you do! So the things I am wishing I had may not seem so wintry 😉

    * black low-ish booties — I have a decent pair of camel low heeled booties, but none in black, and I would get a lot of wear out of them!
    * a chunky knit, drape-front, loose cardigan but long sleeved. I have a short sleeved one and it’s nice and cozy, but not quite enough when I need a sleeve. A LS one would be perfect for in between weather days when its too cold for a leather jacket but too hot for my cocoon coat.
    * I’ve had my eye on a Ines Atelier D1 leather jacket — she hand-makes them in Croatia, and they’re only about $900. OK, $900 is a lot, but on par for a good leather jacket, not to mention custom fit! A big purchase to be sure, but one I am excited to make happen this year.
    * my friend is making me a chunky black knit double-pom beanie (toque) and I wish it had been done months ago! 🙂
    * a long sleeve chunky knit crop sweater. probably not cashmere, as that’s too hot. something breathable but not as warm, like a cotton based knit.
    * a silk cami, probably in white! perfect for tucking in to jeans or high waisted pants, of which I have a variety. not exactly a winter item 😛

  6. Koyuki says:

    Yes! Those are the exact midcalf No 6 that I have. Love em!

    Have your opinions about the ponte pant vs Cecilia pant changed any?

    Also, I’m sending you an email about a tangentially related matter. ?

    • Lee the Bee says:

      That’s great to hear Koyuki! I’ve worn my Ponte Pants more this winter since my Cecilia’s are quite cropped on me and I can’t tuck them into boots. I’m planning to order a long inseam pair later this year because they really are the best slim black pant. Got your email! Excited to check out your zine 🙂 xo

  7. Desta says:

    Wonderful post, Lee! I never used to enjoy getting dressed in the winter either, mostly because I always felt like I had nothing to wear. But with some work and a bit of attention to my needs (I live in Chicago–so cold! need so many sweaters!), I have realized that I almost never struggle with what to wear anymore. It helps that I’ve found a simple template that works for me–button down (I love Tradlands for these), cardigan/sweater, high-waisted jeans, and something that pops (beautiful patterned headwrap, statement earrings, or jaunty neckerchief). I think that fun/whimsical/colorful component has been really important–I’m really good about that in spring/summer, mostly because there are so many fun patterns to play with, but I need to remember that winter requires some lightness too if it’s meant to be endured. Now my goal is to practice a bit more contentment–Lord knows I already have so many button-downs and sweaters!

    To that end, next year I don’t think I’ll be needing/wanting very much. A few things I’m thinking about are a pair of Bryr clogs (Suzie in Sienna) and a gray overcoat (the photo you posted above is spot on what I’m looking for–keep us posted please on what you find!). I’m always on the lookout for a pair of nice black riding boots I can love as much as my cognac Frye boots, but alas, that one has required some patience, especially since I have exceptionally narrow calves.

    Have a restful weekend!

  8. What an incredibly informative post! This is exactly how I wish my wardrobe looked, I am always on the look out for staple pieces and I think I’ve found a lot of them right here! I feel like this post is the perfect visual representation of the ‘wish list’ I have saved on my phone currently haha!
    My most worn piece at the moment is probably a pair of & Other Stories black pointed chelsea boots which are a MUST have for me – I searched far and wide for the perfect pair! I am also a huge fan of neutral scarfs, I have recently purchased a camel scarf which I have already worn to death. X

  9. Lauren says:

    I love this! I recently followed a similar process as I decluttered my fall wardrobe and switched it over for winter. I surprised myself by reducing my 35 piece wardrobe to a 24 piece just by omitting the items I didn’t wear often or feel good in! One of my favorites this winter has been a simple grey cashmere crew from Everlane. It’s so comfortable, but instantly makes me feel more pulled together.
    Thanks for sharing!

  10. About to visit Vancouver for a week of yoga and down time…so this post was super-timely, helping me get clearer on my “winter wish list” before considering any purchases there. Thank you!

    Grey and black cashmere sweaters get the “most worn” award in my winter wardrobe this year (two from Everlane, one from J.Crew). I find I’m not so satisfied with my pant options – everything is too big (probably a couple sizes too big), but I don’t feel comfortable, cozy or myself in tighter pants. Still working on this…

    And still in need of items I identified earlier in the season: an additional scarf or two, an additional toque or two, a winter coat. I’m just not interested in adding to my closet anymore until I find things I love made from natural materials.

  11. Meredith says:

    Hi Lee.

    Love reading your thoughts!

    I’m saving my pennies for a black pair of Sevilla Smith Terilyn boots. I’m new to the ankle boot world and but have really worn my first pair a ton this season (I have myself some 2nd hand Mars boots in Whiskey thanks to you 🙂

    Quick question. How oversized do you find your cropped everlane sweater? I’m wondering if I could get away with an L? I know their sizing can be a bit erratic!

    • Lee the Bee says:

      Thanks Meredith! So glad you’ve enjoyed your Mars boots! They’re my personal faves for sure. I ordered a size up in the cropped sweater (for me that’s a M) and it’s quite roomy. The Small would have still been roomy but a little slimmer in the arms and torso. Everlane should have all the flat measurements for the different sizes available so my suggestion would be to compare a sweater you already have to see what size is best. Hope that helps! xo

  12. Tina says:

    Happy Friday, Lee!
    Another inspiring post from you – did you realize how many of your 8 featured looks are from your 10×10? I really have to say, the 10×10 was a worthwhile experiment and it opened my eyes more to what my favorites are and what works for me.
    Let me tell you how I gave up on an item on my wishlist: I had a fitted, soft turtleneck on my list since November, and I must have tried on at least 20 in different stores. I tried the second hand shops too, but there wasn’t a single one that I liked 100 %. So goodbye fitted turtleneck. I’m happy to be able to admit it that they don’t work for me. (Until last year, I would have bought one anyway and then ended up not wearing it.)
    Right now, black chelsea boots are the next thing I’d like to add.
    Thank you again for your approach on keeping a thoughtful wardrobe – and for the way you put that in words.
    By the way, I LOVE your kitty Evie!

  13. Anna-Lena says:

    Hello from Stockholm, Sweden. Great post! I also found you through the 10×10 challenge, and I am so glad I did! The amount of work that has gone into this post is truly amazing. And the result is so inspiring. Can’t wait to follow you tips. Have a great weekend.

  14. April says:

    I found your blog through your winter remix collaboration with Caroline of Unfancy, and I love it! I’ve been thinking about some items I’d like to add next winter, sort of creating an informal winter wish list in my head, but I love the practicality of a well considered wish list moving forward. Thanks for the inspiration!
    Winter 2017 wish list:
    A-line cashmere sweater dress
    Black or Dark Charcoal wool clogs
    FashionABLE leather tote
    Winter (duck) boots

  15. Emily Mahi'ai says:

    I have the same problem with the T sweater not being warm enough, and it doesn’t even snow where I live (it does still get pretty chilly, with lots of rain and some hail, enough to make my bones and joints ache like hell). This is the first winter I’ve owned anything wool and oh my gosh, it helps so much.
    For my list, I need another pair of cute, sturdy boots, preferably in brown. I’ve worn my black pair of boots into the ground, and they’re not so cute anymore. ? But I’ll probably wait till next fall to purchase them, winter won’t be lasting much longer here (wish I could send you some of our spring weather!)
    Also on my list are a pair of Kamm pants, a gray button-up from Tradlands, some high-rise indigo slim or straight denim, and a nice coat (probably Everlane?).

  16. Hilary says:

    Can’t wait to try my own Winter Wardrobe Assessment! As usual, I really appreciate how you broke the process down, Lee. I’m totally on board with your sentiment: “It’s all about learning what works and what doesn’t, not about what stays or goes.”

    During this winter, I’ve made a pretty big realization that I have an excess of sweaters that are *too hot* for regular wear, and barely any that keep me just-right cozy (but not sweaty) for the season. So I’m totally feeling your Goldilocks syndrome! My wardrobe is definitely in need of a few pieces that are *just right*. I’ve even noticed that I wished I had mocknecks instead of turtlenecks, sometimes. For some reason the fold-over/double-layer of a turtleneck is making me burn up this season. I think those Everlane cashmeres might be calling my name – how do you find them in terms of warmth? I live in Cleveland, which is not unlike Canada in its freezing temps and excess of snow! 😉

    Thanks as always for your insightful posts!

  17. Rita Tocta says:

    Your posts are amazing your insights priceless. You have a different special voice in the blogsphere! I’ve recently took note of how much I love big chunky white pieces in the Winter but never really paied attention to that in my shopping. Lately I had big epiphanies about a lot of looks I like (I really do) and I look good (I believe ;)!) in them but still they don’t feel right. I almost couldn’t believe when I discovered that. The thing is that being very sensitive aestetically there are things I do love (it’s not a mistake I do like them not because they are on trend,etc) BUT I don’t necessarily want to dress them. They are pieces and styles to be admired like paintings I love but I like to see in a gallery (not take home with me).

  18. Jodie says:

    Love love love this Lee!
    I wish you had shared more of your 31 core pieces!
    Outfits 2, 3 and 4 are the formulas I wear all the time!
    I have that Everlane cardigan and t shirt. Both are A+s!
    Definitely size down in the cardigan though.

    Next winters wish list:
    Aritzia cocoon coat (cigar, just like yours- so classy!)
    Blockshop textile scarf
    Everlane cashmere in black, or tan color.
    Black chunky tunic sweater
    Sweater dress (light gray?)

    Have a great weekend! Xo!

    • Lee the Bee says:

      Thanks Jodie! I appreciate the thumbs up on those Everlane items and the sizing tip Sounds like a great wish list you’ve got! Super versatile pieces that I’m sure you’d get lots of use out of.

      Quick question: Do you mean you wish I’d shared more on why the core pieces work for me? Or did you have something else in mind?

      Thanks for reading and have a great weekend! xoxo

  19. Cara says:

    Thank you for your posts! I started reading your blog during this 10×10 and it is so beautiful and your posts really speak to me. Love the idea of cultivating a wish list for the same season a year out to make it realistic and avoid those impulse buys.