Okay, so today I’m gonna share my experience with pairing flat boots and dresses. It’s a combo I love, but it took some trial and error to get right.

First off, I had this idea stuck in my head. I saw some pics online and thought, “Yeah, I can rock that!” So, I grabbed a flowy midi dress – it’s got a floral print, kinda boho style. Then I pulled out my trusty flat ankle boots. They’re just plain black leather, nothing too fancy.
The first try? Total disaster. The dress was too long, and the boots made my legs look stumpy. I felt like a frumpy old lady. Not the vibe I was going for AT ALL.
So, I didn’t give up. I figured the problem was the length of the dress. I dug out another dress, this one a shorter, almost mini length, but still pretty loose and casual. It’s a solid color, a sort of olive green.
Round two with the same black ankle boots… better, but still not quite there. The shorter dress helped with the leg length issue, but the outfit felt a bit… basic. Like something was missing.
I started playing around with accessories. I added a long necklace. Nope. Then I tried a wide belt to cinch in my waist. Still no. Finally, I grabbed a denim jacket and tied it around my waist. YES! That’s what it needed. The jacket added some structure and a bit of edge.

But I wasn’t done yet! I felt like the black boots were too harsh with the softer dress. I remembered I had a pair of brown suede flat boots tucked away in the closet. They’re a lighter color and a bit more casual.
Swapped the boots, and BOOM! That was it. The brown suede boots softened the whole look and made it feel more cohesive. The shorter olive green dress, the brown boots, and the denim jacket tied around my waist. Finally, a win!
Here’s what I learned:
- Dress length is KEY. Midi dresses can be tricky with flat boots, especially if you’re not super tall. Shorter lengths usually work better.
- Don’t be afraid to experiment with different boot styles. Ankle boots are a safe bet, but try different colors and materials.
- Accessories can make or break the outfit. A belt, a jacket, a scarf – they can all add that extra something.
- Don’t give up after the first try! Fashion is all about experimentation.
So, that’s my flat boots and dress journey. It wasn’t always pretty, but I got there in the end. Hope this helps anyone else struggling with this combo!