Winter 10×10 – Look 7


Is it really Wednesday already? Time sure does fly when you’re having fun and we certainly are with this #WINTER10x10 Challenge, even though things don’t always go as planned. Yesterday, Caroline, of Un-Fancy and I both had some issues with our outfits, but we embraced the parts we didn’t love and learned some things for next time.

I learned I don’t love oversize cropped sweaters with skinny jeans while she learned she doesn’t love so many dark pieces in one look. In Caroline’s words, ‘How Fascinating!‘. It’s not about a flop or a hit, it’s about the learning process and the freedom to take risks and then assess the results. That’s what this 10×10 Challenge is really all about. If every outfit felt perfect and chic, well, there wouldn’t be much point in doing it!

If you’re new to the 10×10 Challenge it’s never too late to join in and you can learn everything you need to get started from this post and get lots of tips and info on this page as well. We’d love to have you!

Today I’m sharing Look #7 so let’s not dilly dally and dive right in! 

Style Bee - Winter 10 x 10 - Look 7 Style Bee - Winter 10 x 10 - Look 7


I am SO DOWN with this outfit. Now I’m just wondering how the heck have I never worn it before!? It’s checking all my personal style boxes without hesitation. It’s versatile, considered, clean and even has that little bit of distinctiveness I’ve been striving for. I feel put-together, totally myself and ready for anything the day throws my way. Man, is that ever a good feeling!

Truth be told, this shirt was collecting dust on the hanger before I shook it off for this challenge. But once again I’m reminded that the classics may go dormant but they never go out of style. It’s been washed a zillion times and it’s ridiculously soft which gives it the perfect drape when tucked into high-rise pants.

I’m really feeling the vintage vibes throughout this look too. The collared shirt, the wide-leg trouser, the black rimmed glasses and the little leather bag are each giving a nod to timeless design. I’d like to think I could have worn this 30 years ago and could still wear it 30 years from now and still feel the same about it. Okay, maybe that’s a stretch but not impossible right!?

One of my main takeaways from this challenge so far is that sometimes simplicity is the statement. You don’t need to fuss with layers, or strategize about accessories or even contemplate colours. Just trust your instincts, keep it clean and true simplicity says it all.

Style Bee - Winter 10 x 10 - Look 7 Style Bee - Winter 10 x 10 - Look 7


1 | TINY POOF | When I accidentally cuffed one of these sleeves only part way I noticed that it created the illusion of a slight poof in the sleeve and I LOVED it! It doesn’t actually make the sleeve billow out more than normal it just makes the wrist a bit narrower giving the appearance of a puffier sleeve. I also like that it’s more snug on my arm so the cuff won’t unroll as the day goes on. You bet I’ll be keeping this trick up my sleeve! Sorry, had to. It might be hard to see in the photos but it’s most apparent in the first one and the image below. 

Try giving your cuffs a short fold so the end comes just over the seam. It’s an easy way to add some style without getting too many folds involved.

2 | TO THE TOP | I used to think that buttoning your blouse or shirt to the top was comically nerdy, but now it’s my go-to move! I love the look of a fully buttoned top, especially when it’s also tucked in. This trick instantly elevates any old button down. My high-school principal would be so proud of me now! Bonus: It’s also a little bit cozier with the collar pulled tight. 

Next time you’re trying to freshen up a button-down, try buttoning it all the way up and tucking it in. You’ll get an immediate infusion of Keaton meets Hepburn (Katherine that is), which will totally revitalize your day. Promise! 

3 | BLACK + BLUE | This colour combo is seriously growing on me these days. It’s feeling fresh and fun and it takes me out of my typical neutral zone without being too drastic. Now, I know this is ‘chambray’ so it’s not technically ‘blue’ but just let me have this one okay?

Next time you’re stumped for a colour combo try a light chambray and black or white. It’s a failsafe combo that’s always refreshing.

4 | GEEK CHIC | This outfit is just short a pocket protector and a pair of suspenders to be a true ‘nerd’ costume but I don’t care one bit. I kind of love how it plays on that motif but employs some stylish elements (like a pair of semi-gloss boots and some sassy pants) to offset it just enough. It feels contemporary and stylish with a major nod to some timeless classics. Oh and there’s totally a protractor in my purse!

Don’t be afraid to start with of a look that’s ‘too much’ of a certain theme. Go for it to begin with, then scale it back and switch things up just enough to feel modern and chic. 

Style Bee - Winter 10 x 10 - Look 7 Style Bee - Winter 10 x 10 - Look 7


It looks like some warm winds are rolling in for today and the rest of the week. HOORAY! After a crazy cold weekend and a freezing rain storm start to the week, no one is complaining about +4ºC and cloudy.

Warmer weather sure is easier to style for too! I’ll simply be tossing on my alpaca wool knit beanie and my caramel coat for the day’s activities. Those being a day in the office, some errands around town and a chill evening visit with my sister-in-law to get caught up on The Bachelor!

Is anyone else always highly entertained by what they choose to wear on that show? I know I’d stick out like a sore thumb in this outfit and to be totally honest that makes me pretty pleased!

Style Bee - Winter 10 x 10 - Look 7

Be sure to pop over to UnFancy for Caroline’s latest 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).


  • CHAMBRAY BUTTON-DOWN | This exact style is no longer available through Everlane but they make a Relaxed Poplin Shirt ($ 65 USD) is a very similar look and fit. | I used to have this one from J.Crew and wore it all throughout school until it finally disintegrated ($ 110 CAD) Imported.
  • 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 ($235 USD)
  • COAT | ARITZIA Wilfred Cocoon Coat ($ 225 On sale!) Imported. | Similar by Madewell ($340 CAD) Imported.
  • BAG | Vintage. Love this one by The Stowe ($353 USD On sale!) Made in Canada. and this one by Cuero&Mør ($252 USD) Made in Spain.
  • BEANIE | No longer available. Similar from Madewell ($41.50 CAD) Imported.
  • FRAMES | Wilson by Garrett Leight (Wearing the 46 mm $310 USD)

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 Style Bee! All opinions are always my own.


Leave me a comment here!

  1. Hannah says:

    I’m finally back to full closet access after the challenge, and I loved the idea of styling chambray like this outfit. So guess what I’m wearing today?! ? Thanks for the ideas! 10×10’s are inspirational for my own closet, but seeing other ideas from others is so helpful too!

    • Lee the Bee says:

      Ah! That’s great Hannah! So glad you gave it a go 🙂 I totally agree about how seeing other people’s looks can be really inspiring. Sometimes it’s such a simple approach but you might not have thought of it otherwise. Hope your weekend has been great so far! xo

  2. Jill says:

    I loved this outfit so much I wore it yesterday!!! It was the perfect look for my day — spotted this in my email inbox, took all of your advice, and was ready to go and looking good in a flash! Love what you do — thank you so much!!

  3. Lynn says:

    Chambray all the way! I love that you ladies are doing this challenge.

  4. Yes to Geek Chic, Lee!

    I’m a nerd through-and-through…but also have an edge accentuated by black faux-hawk hair and a black-and-red Japanese dragon tat covering one arm and wrapping around my shoulder blade. I love pairing those “accessories” with looks where “simple is the statement” and that statement includes a strong nod to my nerdy (and Chinese Medicine doctor and teacher) side.

  5. Tina says:

    Hi, I love checking your and Caroline’s outfit every day! Funny, yesterday must have been the not-so-crazy-about the outfit day. I felt like that too with a sweatshirt over silk dress and faux leather leggings in the morning. Planned nicely in my head, I didn’t really like the look of the real outfit. I was tempted to change but decided give it a try and wear it to work. Surprisingly, it didn’t feel so bad as the day went on. Do you wear an outfit all day or at least for work when you are not content with it?
    You say that one of your main takeaways of the challenge is to make simplicity the statement. For me, the opposite seems to be one of the lessons learned: I had fun choosing the accessories carefully and paid a lot of attention to the right belt, scarf or bracelet.
    I never thought I was going to have so much fun doing the challenge in two work-packed weeks – gotta check on Caroline’s post now!

    • Lee the Bee says:

      Thanks Tina! Thanks so great to hear. Since I work from home I’ll typically change if I don’t love an outfit. But if I’ve gotten distracted and worn it for much of the day I’ll usually just stick it out.

      Love hearing about everyone’s different takeaways! Glad you were able to zero in on how accessories come into play for you. So glad you were able to join in! xo

  6. Adore this look. Funny story, I have a similar outfit that I wear sometimes, and I’m currently in a musical that’s set in the 70’s and I’m wearing it as one of my costumes. ? My mom calls it my “angry feminist from the 70’s” look, and I love it.

  7. I love how simple this is, Lee! I’ve also been buttoning up my collared shirts all the way, but I haven’t tried fully tucking them so that’s next on the list. 🙂 My younger brother’s friends commented on it one time so I’m not sure if that makes me cool or uncool (I’ll go ahead and take it as a compliment haha). I would *love* to see someone on The Bachelor dress like this, no lie. I’d be so impressed. Some of their outfits are just…yikes.

    • Lee the Bee says:

      Thanks so much Kimi! I would definitely take it as a compliment. Boys (aside from my fella) are rarely big fans of how I dress and I’m totally fine with it haha.

      I honestly don’t know where they find some of their dresses! Such gorgeous women in such ridiculous clothing 😛

  8. Stacy says:

    It’s always a great feeling putting on an outfit you feel yourself in after having an “I don’t really like my outfit day.”
    I’ve loved seeeing how versatile you’re black Kamm pants are over the 10×10 challenge! Each look with them has been so different and lovely. I had always thought of my wide leg pants as only a Spring/Summer style, and usually put them away for the winter, but you’ve given me lots of inspiration to try them in the cold! Thanks for your unique sense of style and fresh take on minimalism.

    • Lee the Bee says:

      Couldn’t agree more Stacy! I used to think the same about wide legged pants but have found them totally wearable this season. It does take a bit more consideration (and some warm socks) but it’s worth it to keep them from collecting dust!

      Thanks so much for the kind words and for stopping by! xo

  9. Eva says:

    Love this, though I still can’t button-up all the way. It’s not so much the geek problem, but that it feels too tight around the throat (I don’t have that problem with scarves). Maybe one day, but in the meantime I’m always happy to pair chambray with everything.