I’m halfway through my winter 10×10 challenge and it’s been a blast seeing what all the #10x10friends have been wearing over on Instagram. Of course, 10×10 guru, Lee has been killing it with her polished, minimalist outfits. And I’ve also been getting tons of inspiration this week from Andrea, Lo, Krystal and Chloè.

If case you’re wondering, this post explains what the 10×10 challenge is, why I decided to do it, and what my goals are for the 10 days.

My Wardrobe Boredom

For me, this wardrobe challenge has been an exercise in getting me out of my wardrobe doldrums by forcing me to be more thoughtful about my outfits. When I get dressed on any normal day, you’ll find me grabbing at whatever happens to be clean and hanging in my closet.

And if I’m being honest, it’s often dirty and balled up on the floor.

But I have two little kiddos so don’t judge. And in case you’re interested, I just graduated from the two-under-two club, and I survived (mostly) unscathed.

There were days when it was a struggle to keep my head above water – like the day my son fell on his face and chipped his two front teeth. It was barely a week after my daughter was born, so I was mega-hormonal and mega-stressed and mega-overwhelmed. My husband came home from an outing with my son, announced that there had been a “little accident,” and showed me my perfect little boy’s now not-so-perfect little smile. Of course, my hormones took over and I started sobbing uncontrollably for the rest of the day.

But there were also days when my heart overflowed with joy. Like the day after we brought my daughter home from the hospital and my son, who hadn’t been saying any words, learned how to say her name in a few hours. And the day when my daughter laughed hysterically at my son for the first time. And every day when I see their amazing brother-sister bond grow.

During those first six months after my daughter was born, on good days and bad days the same, my personal style took a backseat. Not much thought went into what I wore, which meant I was wearing a lot of t-shirt and jeans outfit repeats. And that led to a lot of boredom with my wardrobe.

The 10×10: A Time Saver

Now that I’m out from underneath the two-under-two haze, it’s still not easy for me to spend the time thinking about what to wear in the morning. So this wardrobe challenge has really helped to force me to think about my clothes for more than two seconds in the morning.

A few days before the challenge started, I spent about 10 minutes brainstorming outfit ideas. I came up with more than 10 outfit candidates and wrote a quick Evernote listing all of them. When I get dressed in the morning, I can look at that list and I don’t have to spend more than a second thinking about what to wear.

I’m not saying I’m going to start listing out all of my outfits ahead of time, but doing this exercise has helped me get more familiar with how I can pair my clothes into a bunch of different looks.

My First Five Outfits

Day One.

Winter 10x10 2018 Outfit 1 | navy Tradlands tunic | black tee | everlane boyfriend denim | white veja sneakers | curatedcassi.com

[Navy Tunic (Tradlands) | Basic Black Tee (Everlane) | Blue Boyfriend Denim (Everlane) | Sneakers (Veja)]

One of my goals for this challenge was to get comfortable wearing this tunic, so I decided to just dive right in and wear it on the first day. I chose to wear it open over jeans – something I’ve never tried before. And to be honest, I don’t love the way this outfit came together. I think the open tunic looks like a painter’s smock and just isn’t that flattering on me.

The Verdict: Probably not going to wear it again.

Day Two.

Winter 10x10 Outfit 2 | Army Jacket | black tee | Everlane boyfriend denim | white veja sneakers | curatedcassi.com

[Green Army Jacket (Lucky Brand, old, similar) | Basic Black Tee (Everlane) | Blue Boyfriend Denim (Everlane) | Sneakers (Veja)]

I resurrected this army jacket from the depths of my closet where it’s been sitting since we moved to San Diego almost four years ago. I’m not sure why I’ve been ignoring it because I actually really like it.

We’ll file this look under the “Classic Cassi” category because I’ve been wearing similar outfits for years. It’s a trusty jeans and t-shirt combo with a little added interest from the army jacket.

The Verdict: I’m sure I’ll wear this or something very similar again. However, I do want to start evolving my style to a place that’s a little more sophisticated and a little less tomboy.

Day Three.

Winter 10x10 2018 Outfit 3 | chambray shirt | black skinny jeans | Nisolo black chelsea boots | curatedcassi.com

[Chambray Shirt (Rails, similar ethical) | Black Skinny Denim (Madewell, similar ethical) | Chelsea Boots (Nisolo)]

This chambray shirt was the first thing I bought for myself after I decided to update my closet. I wanted a button down for layering and had been admiring the look of a chambray for a while.

I like the simple dichromatic look of blue chambray over the black skinnys. And I’m finding that my Chelsea boots magically make everything look cooler. This outfit makes me feel like a sassy twenty-year-old!

The Verdict: I’ve been wearing this exact outfit and some variations a lot lately. So it’s not a completely new look for me, but it’s a winner.

Day Four.

Winter 10x10 Outfit 4 | Oversized sweater | Navy Tradlands Tunic | Black Madewell Skinny Jeans | Black Nisolo Chelsea Boots | curatedcassi.com

[Oversized Sweater (thrifted, similar ethical) | Navy Tunic (Tradlands) | Black Skinny Denim (Madewell, similar ethical) | Chelsea Boots (Nisolo)]

My second attempt at styling my navy tunic was much more of a success. I wore it underneath an oversized sweater with black skinnys and black boots. I played around with a similar sweater/tunic look a few weeks ago and liked the result, so I wanted to try it with this tunic. I’m digging the color palate of this outfit and the way the navy tunic frames the sweater at the neck, cuffs, and hem.

The Verdict: Love it! I’ll definitely put this in rotation for days I want something comfortable but a little dressier than a t-shirt.

Day Five.

Winter 10x10 2018 Outfit 5 | Chambray Shirt | Black Tee Everlane | Black Skinny Jeans Madewell | White Sneakers Veja | curatedcassi.com

[Chambray Shirt (Rails, similar ethical) | Basic Black Tee (Everlane) | Black Skinny Denim (Madewell, similar ethical) | Sneakers (Veja)]

More dichromatic blue and black made its way into my outfit on day five. I felt like this outfit was a little uninspired and too similar to what I wore on day three. Since I have photos and I can compare the two outfits side-by-side, I’m thinking the unbuttoned chambray is less flattering on me. This is interesting because I always wear my layering pieces open – but maybe I should start buttoning them.

The Verdict: I don’t love it, but I might wear it again.

Have you been participating in the 10×10? What new things have you learned about your style?