Style Bee - Winter 10 x 10 - Look 1

Winter 10 x 10 – LOOK 1


First of all, can I just say how thrilled we are that so many of you have decided to join Caroline, of UnFancy, and I for this #Winter10x10 Challenge! We’re totally blown away by this community and it’s been such a treat to see your outfits and read your thoughts on style so far. Keep up the great work!

If you didn’t or couldn’t join in this time that’s totally okay! There will be more challenges in the future and you can always do one on your own time if that works better.

But right now it’s outfit time! I must admit I really missed sharing looks during my two-week winter break. It’s especially nice to be back with one that I’ve never worn before but that still feels so in line with my usual go-to style. So let’s have a look shall we?

Similar to the last challenge I’ll be breaking the outfits down the following way:

  1. Initial Thoughts – My immediate reaction to the outfit, how I feel wearing it and what stands out (good or bad).
  2. Style + Fit Details – A few unique elements that I considered when putting the look together.
  3. Outside – I’ll also be sharing a short note about what I’m adding to make the look cold weather ready!

Style Bee - Winter 10 x 10 - Look 1


Right away I’m at ease in this one. Sure it’s not breaking any style sound barriers but it’s also not boring (at least not to me!). I’m comfy in flat boots, cozy in my cashmere sweater and feeling a little stylish in my wide-leg pants. It’s still snowing out though so I’ll need to switch to my Sperry’s when I head outside.

I could wear this look for just about any occasion my usual week calls for. Coffee dates, client meetings, studio time and dinners with friends or family. It’s dressy enough but not too corporate or formal feeling.

Now this is a lot of rich colour for me. The merlot sweater with the caramel bag and the mosaic scarf is more colour than I’d typically go for but I’m kind of into it for this time of year. I’m used to having some lighter neutrals in there to soften things a bit but it’s good to push the limits with colour sometimes!

I do wonder how these pants are going to fit/feel after an entire day and if they’ll stretch out much. I’ve worn them lots of times but not for 8 hours straight. I suppose I’ll know by 5pm tonight!

These glasses are starting to become a key element in my personal style even though I’ve never identified as ‘the girl with glasses’. I used to always feel like they were hiding my face or offsetting my style in a weird way. But with this pair I totally forget they’re on and then I’m pleasantly surprised when reminded. So glad I saved up and invested in a high-quality, well-designed set of frames and lenses. Link below.

Style Bee - Winter 10 x 10 - Look 1 Style Bee - Winter 10 x 10 - Look 1


1 | WINTER CROP | Even though it’s really cold and snowy out I still think crop tops are a viable winter option. Now, hear me out! For instance, this cashmere crop sweater is one of my most worn winter items. Plus, as you may know, I’m not into revealing crop tops but more so their ability to create interesting shapes and give the illusion of longer legs, which this one is great for.

I’ve found that this combination of crop top length + waist height is just right for me this season (and all seasons actually). The high waist and wide leg create a long lower half and the bottom of the sweater hits just below my natural waist for a visually slimming effect that’s not too drastic. I wear a bodysuit underneath (like this one) which adds warmth and extra insurance that no skin will be exposed.

Additionally, the cropped hem on these pants keeps them out of the snow and off the ground. This is a key factor in their being winter weather appropriate. I love my flares but they just get too salty and slushy this time of year!

Try thinking about the top and bottom combos you love. What is it about the way the two fit that works for you? Keep that in mind the next time you shop.

2 | BRIGHT LIP | I’m not big on experimenting with makeup trends but I’ve been loving a bold lip this season. In this instance I went for a warm berry hue and layered on a couple colours to get something similar to my sweater but a bit brighter so it would stand out. It’s amazing how much energy you can inject to a look with something as simple and quick as a good lip colour. The Burt’s Bees combo I used is linked below.

Would you consider trying a bold lip to freshen up your look this season?

3 | COLOUR COORDINATION | I love when the colours in a look integrate nicely without being overtly matchy. This scarf manages to have all three colours from this look mixed into a pattern of primarily blue and purple. It has caramel (like my tote), flecks of burgundy (like my sweater) and touches of black (like my pants). I added it for the pop of pattern without realizing it was such a cohesive way to finish the look.

Next time you’re adding accessories think about the colours involved and how they can play on what you’re already wearing.

4 | BIG BANDANA | Instead of the usual wrap around style I opted to tie this lightweight scarf like a bandana. I folded it in half, then point to point (not end to end), to create a triangle shape, then tied the longest edge around my neck. This creates a nice slouchy ‘v’ in the front and I love how it looks! It’s easy to tuck into a coat and the back doesn’t turn my hair into a knot-fest. WIN!

How do you tie your scarves to keep them from getting too bulky?

Style Bee - Winter 10 x 10 - Look 1 Style Bee - Winter 10 x 10 - Look 1


To make this look winter weather ready I simply add my black wool coat, which you might recall from my FALL 10×10. It’s been a staple for me this season and I love the sophistication it adds to any outfit.

If it’s really frosty out I’ll add a knitted toque and a pair of gloves.

I’ll also be wearing a bodysuit (like this one) underneath for added insulation. I find a layer underneath helps my sweaters feel fresher for longer too!

These pants are easy to slip on over a pair of warm knee socks or even tights so my legs don’t get too drafty!

Style Bee - Winter 10 x 10 - Look 1
So there we have Outfit #1!

Be sure to pop over to UnFancy for Caroline’s first one too!

+ Keep sharing your looks with #Winter10x10 and if you have a sec, check Instagram Stories today for a real-life look at our outfits in action (@caroline_joy + @leevosburgh).

See you there!

  • SCARF | Old from Urban Outfitters (linked to similar option $40 USD) | My favourite lightweight scarves are from Block Shop Textiles ($120 USD)
  • SWEATER | Cropped Cashmere ($115 USD) by Everlane (low stock, similar style here for $130 USD) Fit note: I sized up from S to M for layering purposes. | Other options by Eileen Fisher ($380 USD) + Amour Vert ($108 USD)
  • KAMM PANTS | Jesse Kamm ($325 USD) Available in Many Colours Fit note: I’m usually a 26 in denim and wear a size 4 in these. | Similar by NEED ($ 115 USD) + Everlane ($78 USD)
  • CHELSEA BOOTS | RACHEL COMEY ($339 USD) Exact pair on sale and available in size 6, 7, 8. | When you sign up via this link, you save $20 and I receive $20 credit when you shop (1 time only). | Also love this pair from EVERLANE ($235 USD) |
  • COAT | Reformation (n/a similar style here by Everlane $265 USD)
  • TOTE | Cuyana ($175 USD Made in USA)
  • FRAMES | Wilson by Garrett Leight (Wearing the 46 mm $310 USD)
  • LIP COLOUR | Burt’s Bees Lip Crayon in Napa Vineyard and Lip Gloss in Summer Twilight

This post is not sponsored but contains affiliate links. When you shop via the links above I may make a small commission from a sale. Thanks for supporting the brands that support Style Bee! All opinions are always my own.


Leave me a comment here!

  1. Katie says:

    I love this look! I would’n’t have thought to pair the sweater and scarf colurs but it looks so classy. I definitely took inspiration from this look for my outfit today and I’m feeling put together, so thank you! I am loving your more everyday looks, and the fact that I can replicate them with pieces I already have in my wardrobe. 🙂

  2. Love the combination of dark reddish colours + black, Lee! And love the permission to not count underclothes worn to warm in this 10×10. Here in BC, it’s not quite as cold as you get…but I still feel it (particularly after my daily, early-morning plunge in a glacial lake!

    My biggest plunge for this challenge will be actually wearing a black raw silk Marlena Midi Dress from Elizabeth Suzanne. I *don’t wear dresses*…but requested it as a gift after the fall 10×10 and LOVE it. Now just need to muster up the nerve to wear…well…a dress.

    Thank you for your continued inspiration!

  3. Lauren says:

    This look is so fun Lee! I love the combination of the bandana and sweater, and also the bold lip color! So beautiful for winter!

  4. Justine says:

    Looks super comfortable but still very stylish.

  5. I wore a scarf in my first 10×10 outfit that pulls in colors from other items, so now I feel cool since you did it too! 😉 I really want to wear my Everlane cropped cashmere with high-rise pants but none of mine are quite high enough and it’s a bummer.

  6. Ally H says:

    Love how you’ve used the scarf to add interest. Am earmarking the idea for another day to jazz up a plain sweater!

  7. Tina says:

    Hi, I love the 10×10 with my two favorite blogging girls. At first I thought, nah, this is such a busy workweek, and I am just going to enjoy your outfits every day, but this morning I thought YES! I’m in! Outfit 1 was found by impulse. I haven’t decided on all 10 items yet and I have to admit, I like the idea that I can add over the next few days.
    Question for you: do you like to try out new items or rather stick to old favorites that you know will work?
    Looking forward to tomorrow’s outfit!

    • Lee the Bee says:

      Thanks so much Tina! So glad you decided to join in. I think adding as you go is kind of genius! Good question. Typically, I’ve tried out a 50/50 mix with old and new pieces but this time I only have 1 totally new piece in the mix so I’ve been revisiting old faves. I think both approaches are good. With new items you get to test them out really well and with old items you get to reinvest. Just depends what you’re interested in wearing at the time! xo

  8. Liv says:

    Wow such a helpful post. Thanks for the style inspiration!


  9. Louise says:

    Hi Lee,

    I love your and Caroline’s first outfits because of the shapes and colors. I love the color of your blouse and scarf together, and the shape of the pants, and I loved Caroline’s tent top. One of my favorite shapes of all time.

    I was hoping to create an index of bloggers who are participating in the challenge, so that we can easily find each other. It’s all about the community and getting inspiration from each other, so I thought it would be a real resource if a list of bloggers was created for easy access.

    Here’s a link:

    Leave a comment below if you want to be included!

  10. I’ve followed Caroline for a while, and I’m so glad she introduced me to your blog – I’m so enjoying reading your posts! Love these pants!

  11. Kat says:


    I’m so excited to be joining you and Caroline for the winter 10×10!! I’m on outfit two and I already cheated by adding rain boots because it’s raining in January in WI, and I’m just not going to sweat it! So excited to see all of your outfits, but I’m also loving the Instagram pics and seeing everyone join in!!

    • Lee the Bee says:

      YAY! So glad you’re joining us Kat 🙂 Oh totally, no worries at all! I’ve already cheated too and wore snow boots and my parka out this morning. It’s snowing like crazy here right now. Isn’t it so fun to see what everyone is trying for the challenge? I’m LOVING the feed (and spending way too much time on it haha). xo