Fall dresses and how to winterize them

Florida is still giving us plenty of hot days, but there is an ever-so-slightly coolness in the air, and there’s no denying that we’ve been enjoying that. Locals here have been telling us that October is the month when it finally cools down, and the nice weather (the one you can actually enjoy outdoors) begins, but it hasn’t been the case this past October.

Just because the weather is getting cooler, it doesn’t mean that I (and you) have to give up wearing dresses. And since this year the focus has been on comfortable clothes, dress designs have been reflecting that, example being the muumuu or nightgown-type dresses that became extremely popular lately.

In some ways, I have also been choosing loose-fitting dresses this summer, though you can attribute that to the heat and humidity down here.

It seems that H&M leads the market in wide-cut dresses lately; they’ve been selling out fast, but the common theme I hear with these dresses is that they run large, like really large. In fact, the dress I’m wearing here is from H&M, and I had to go down 3 sizes to avoid looking like I’m wearing a sack of potatoes. It’s sadly no longer available online, but you might still find it in stores. It’s a pretty dress, and it was the colors and print that attracted me to it, and I’m looking forward to wearing it more as the weather cools. For my complete look, shop my espadrilles here, and my backpack here.

Generally, we tend to go for darker colors in winter, but I like to wear bright ones and/or florals - as we lose light in the winter due to the shorter days, it’s nice to wear some color to improve my mood.

Below, I have selected dresses that can be worn into the warmer days of fall (and even winter if you also live in a warmer climate). Many of these dresses would look great with ankle and especially knee-high boots. To winterize them, wear these dresses with tights, and a faux fur vest cinched with a belt if you want to accessorize, or without, for a more casual look. Scroll below for options on faux fur, belts, and tights. Of course, especially with sleeveless dresses, you can always wear a sweater over them (like this crop one, or this), or a jacket.

Which dress do you like the most?