10×10 Winter Challenge

Winter 10x10 Challenge

If ever there was a winter that called for some creativity this is it! Even though most of us aren’t going outside or wearing actual clothing, it can be a fun distraction to put together a 10×10 Challenge.

This was my first 10×10 Challenge, and I enjoyed it so much I plan to do one each season. Its a great challenge to pull things out of your closet you aren’t reaching for often, finding ways to mix and match new pieces, finding new outfits out of what you already own, or dipping your toes into a capsule wardrobe.

If you are unfamiliar with the challenge, it was created by Style Bee in 2015. The challenge is essentially taking 10 items to put together for 10 outfits to wear for 10 days. Those who also participate in the 10×10 Challenge and can offer more inspiration are the blogs: Un-Fancy by Caroline Joy, Mademoiselle by Jamie-Lee and The Anna Edit by Anna Newton.

What I like about the challenge is that there’s no right or wrong way. It’s more about sparking creativity and having fun with your wardrobe. I chose to focus on just clothing and shoes, and leave out accessories and my winter coats.

Winter 10x10 Challenge
Winter 10x10 Challenge

My 10 Pieces


Vintage Gianni Versace knit dress – This dress has been in my closet for over a decade, but I rarely wear it. This challenge has showed me that not only can I wear this dress in the winter, it also looks great as a skirt when paired with a sweater on top.


Quince Mongolian Cashmere Crew in camel – I recently ordered two cashmere sweaters from this company and I was surprised how great the quality is for the price. This color has been a great way to add some color to my wardrobe, matching with both brown and black.

Naadam Cashmere Turtleneck in oatmeal (similar) – I grabbed this sweater in the summer from Thread Up, not sure if it would fit. Thank goodness it did because it is the coziest sweater! Its a great neutral choice to deviate from my normal all black outfit.

Lafayette 148 Split Merino Wool Turtleneck Pullover in black – Of course a black sweater had to find its way into this challenge. An all black outfit is my standard since I don’t have to think much about it and I always feel well dressed.


Frame Striped Button Down Silk Shirt – Recently I’ve been grabbing more pieces in silk, and this shirt is a great choice for the colder months with its complementary colors of beige and black.


Sandro Blazer with Leather Collar (old) – What an amazing find in my favorite NYC thrift shop. I recently found out this is a men’s blazer, which explains its boxier cut. The bit of leather on the collar separates it from a typical black blazer, giving it just a bit of extra personality.

St. John Knit Blazer (thrifted) – A recent addition to my closet, but such an easy piece to style. St. John knits have a great weight to them, and this piece has proved to be versatile. It can be worn either on its own or under my winter wool wrap coat as an extra layer. The grey color is a great neutral pairing well with a variety of colors.


Everlane Authentic Stretch High-Rise Skinny in black – These are my go-to for a basic, go with anything jean. I gravitate towards darker denim as it really does go with anything and elevates your outfit.


Saks 5th Ave Ankle Boots (old) – I jumped on the bandwagon of pointed-toed ankle boots and for good reason. They feel a bit edgier than a round-toed boot and I find myself putting them with most outfits.

Cole Haan 4.ZERØGRAND Hiker Boot in Jaguar Print – Such a fun boot! What is better than a leopard boot that also keeps your feet toasty warm? I was in need of a snow boot, but wanted something with a bit of personality. The brown and black in the boot means it will go with the rest of my winter wardrobe.

Excluded Pieces


Sportmax Wrap Coat (old) – A wrap coat is a classic wardrobe staple. This coat has a bit of an interesting detail to the wrap that I really like. Though I do wish it was a bit bigger to wear multiple layers comfortably underneath.

Mackage Puffer (similar) – Also a wardrobe classic and essential if you live in a colder climate. A longer style is preferable to keep as much of you covered from the cold as possible.

Universal Standard wool scarf – This is a recent purchase. I was a bit skeptical because it is wool, but this scarf is super cozy. Having a black scarf to keep my neck warm but also seamlessly work with my wardrobe is an essential.

Saks 5th Ave cashmere scarf (similar) – I picked up this scarf because not only is it cashmere, which I adore, but also a beautiful camel color. I’ve been trying to add more of this color to my wardrobe and this is an easy way to do it.


Chanel Classic Single Flap Jumbo Beige Caviar Leather Shoulder Bag – This is something I’ve had for a very long time. I’ve thought about selling it because of the color, wanting the black version, but I’m so glad I kept it. It goes so well with the camel and beige tones I’ve been adding to my wardrobe recently, and helps break up all the dark tones I normally wear.

Vintage Asprey convertible clutch – I love pieces that do double duty. A convertible clutch is a great addition to a wardrobe as it can go from day to night so easily. This is the perfect piece for when you are traveling and need to keep your packing light.


Portolano wool beanie (old) – Having a cute but also warm hat is necessary for me in winter. Keeping a variety of different colored hats can be an easy way to add a pop of color to your outfit.


Vintage Fedora – This is one of my favorite thrifted finds. It adds such personality to an outfit, and bonus, can hide a bad hair day.

Uniqlo Thermals – Thermals are a great addition to a winter wardrobe, as they give you that extra warmth and can be used as loungewear. If you are traveling between hot and cold climates, these are great to layer and keep you from feeling that chill.
Heattech extra warm crew
Heattech ultra warm leggings
Heattech tights
Heattech pique crew socks

The Outfits

At first I was struggling to put together 10 outfits. I had in my mind that I needed 10 completely different outfits, but that doesn’t suit how I get dressed. I tend to be a uniform dresser who switches out a jacket or top but keeps the other pieces the same.

I’m challenging myself when adding new pieces to my wardrobe, to go with a color other than black and with shapes or prints that will add more versatility to my wardrobe. But for now, this is what I am working with.

Check out the video below for how I put together my 10 outfits, with some ideas for both mild and cold climates.

If you are struggling to get started, chose your items as if you were going on a 10 day trip and taking only a carry-on. I found thinking about my pieces in this way helped me to figure out what to include. Remember that its about having fun, not about getting it “right.” So you may make several edits before deciding on your final 10.

I hope you have fun creating your own 10×10 challenge! If you have a favorite look or found inspiration in my 10 outfits I would love to hear in the comments below.