The DIY Playbook Style Series: Fall Dresses

The DIY Playbook Style Series: Like many of you, we both strive to buy clothing that not only reflects our style, but is also comfortable, affordable, and can be worn at work AND on the weekends (did we mention we don’t want to spend a ton of money either). We know that a lot of the DIY Playbook’s readers are currently in this same exact situation, so hopefully together we can start this new journey of connecting one another with clothes (and sales!!) that make us all feel confident and comfortable. Don’t get us wrong, we are NOT fashion experts and we are not even fashion forward, just regular girls trying to have a little fun with our styles all without breaking the

Today’s Wardrobe Staple: Fall Dresses

As much as we are jeans & t-shirts gals, we do love wearing dresses every now and again. Whether for work, a date night, or a special event…it’s nice to just throw on a dress and feel instantly pulled together.casey-jacket

In the fall, we both opt for comfy dresses that can be worn with boots and layered with a jacket and scarf (on chilly days), or all by themselves (on those warmer days). We each have a few dresses that we absolutely love and wear over and over again…


I recently added this dress to my fall wardrobe and oh my goodness…I’m obsessed.casey-dress-8

Not only is it super flattering (hides the tummy, shows off the legs!) but it is also so incredibly comfortable and soft!

I’ve worn it with heels out on the weekends, and have also worn it more casual with booties. Both looks are adorable. casey-bag-purse-nordstromPlus, it’s less than $50! I should probably get it in a few more colors….


I also still adore this dress that I wore in Carmel (when the temps were pretty warm.) That maroon color is just perfect for fall & again it’s less than $50. I’m planning to make the outfit work for cooler weather with a jacket, scarf, and boots. So cute & easy!


Remember this casual grey dress from my family’s Christmas Card photo shoot? I absolutely LOVE it because like Casey mentioned, it’s so darn comfy and extremely versatile throughout the fall.

If you haven’t noticed already, I tend to gravitate towards neutral colors. I specifically love grey because it matches with pretty much anything and can be easily paired with any purse, accessory, or shoe.

I scored this dress for $14 (yes $14!!!) at Marshall’s a few weeks ago, but I recently found a very similar dress (at $40) from Nordstrom. I’m a sucker for long sleeve dresses and fall seems like the perfect time to wear some of my favorites. And like Casey said, layering them with boots, scarves, & vests is a fall must! 

For the Christmas card photos I paired this dress with these open toe shoes and for these photos, I went with a closed toe bootie. I also opted for comfort by pairing the dress with my favorite TOMS or even converse for a very casual weekend look! <— see what I mean when I say this dress is versatile! 

If you’re looking for fall dresses this season I have one piece of advice for you — don’t buy a ton of different dresses because one (or two) versatile dresses is PLENTY! Choose a dress that you LOVE, and I’m confident you will get a ton of use out of it! Here are some other dresses that are affordable and have caught our eye this season…

Our Favorite Fall Dresses

1. Navy Dress (less than $50!) // 2. Maroon Dress // 3. Floral Dress (less than $50, comes in a variety of colors!) // 4. Drape front dress // 5. Striped Swing Dress // 6. Black Shift Dress


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.