Okay, so today I want to talk about how to put together a decent outfit with a dress and booties for winter. This whole thing started because I was just staring at my closet, completely stumped. I had this cute flowy dress that I really wanted to wear, but it’s freezing outside, you know?

So, I started experimenting. First, I grabbed the dress and tried it on with a pair of ankle booties. It looked kind of okay, but not quite right. The dress is kind of midi length, and with the booties, it just made me look a bit frumpy. Not the look I was going for, obviously.
Then, I remembered seeing something online about different dress lengths and boots. I dug out a shorter dress, almost a mini, and paired it with the same booties. It was a bit risky, but since my booties are flat, I think it worked. I also added some thick tights to keep my legs warm, because, like I said, it’s cold out there!
- First try: Midi dress with ankle booties – result was frumpy.
- Second try: Mini dress with flat ankle booties and thick tights – this one worked!
Next, I played around with a longer, maxi dress. I found that this actually looked pretty good with the ankle booties too. It created a balanced, kind of feminine look. I guess the key is to make sure the proportions are right.
My Realizations
What I realized through this little experiment is that you can totally wear dresses with booties in winter, you just need to pay attention to the details. Like, a flowy dress can look great with ankle booties, but the length of the dress matters. Also, don’t be afraid to try different styles of booties. And of course, tights are your best friend when it’s cold!
I also found some stuff online about stores that sell good winter clothes, but honestly, I prefer just mixing and matching what I already have. It’s more fun, and it saves money. I spent a good amount of time just trying on different combinations, and I actually ended up with a few outfits that I really like.

So yeah, that’s my little adventure with dresses and booties. It was a bit of a process, but I learned a lot. Hopefully, this helps someone out there who’s also struggling to put together a cute winter outfit. Just remember, fashion is all about experimenting and finding what works for you!
Oh, and one last thing I did: I took some photos of the outfits I liked. Maybe I’ll share them sometime. But for now, I just wanted to share my experience and what I learned. Stay warm and stylish, everyone!