How to Transition a Summer Dress Into Fall

This post contains affiliate links. I make a commission if you purchase these links but it doesn’t affect the price you pay for the item. Thank you for supporting me through your purchases and encouraging comments. You keep this website going! Full disclosure.

On a whim, I purchased this gorgeous dress from Urban Outfitters earlier this year and instantly fell in love. It wasn’t even the dress I went there to buy but I’ve worn it over and over this summer so it was the perfect candidate to come with me into fall.

Unfortunately, this particular dress is only available in limited sizes but this transition formula can apply to your favorite summer dresses too.

I’ve worn it belted and unbelted depending on my mood and how hot I am. 😉

DRESS (wearing a L) || Cute Fall Option || Budget Option (see more below)

BELT || Fall Option (comes in plus size)

HAT || Fall Option

ESPADRILLES Similar

This girl loves a jean jacket to transition anything into fall. You still remember those olive joggers, right?

But let’s talk about the most flattering denim jacket for curvy girls to wear with dresses. Even though a regular denim jacket looks okay here, I highly recommend a CROPPED DENIM JACKET!

They can be hard to find, but they will help define your waist and don’t add width to our already curvalicious booty and hips.

CROPPED DENIM JACKET (mine is older from J. Crew Factory) || Similar Plus Size || Similar

Booties and middie dresses were made for each other.

However, if you have a full calf, finding a flattering bootie can be tricky. In one of my most popular posts ever, I show you that the most flattering bootie for a curvy woman to wear is a front V-notched bootie. I have some linked over there, but they are incredibly hard to find. (The same principle applies to petite women.)

So another option is to choose a bootie that is nearly the same tone as your leg.

BOOTIES – Exact || Budget Friendly (I own both)

*If you have slim legs any bootie will work.

Though not shown here, a cardigan and knee-high boots would also transition some summer dresses into fall.

If you’re slimmer, you could easily wear a longer cardigan over the dress. But I find that for me, a cropped cardigan is still the best option. But that’s coming from a girl with a big booty (bootay) – not to be confused with booties. ;-P

CROPPED CARDIGAN || Another || Another

LONGER CARDIGAN || Similar

BOOTS – Wide & Regular Calf

And oh my goodness, I will do a post on these boots but if you have a wide calf, YOU NEED THESE!

They are one of those recent purchases I was telling you about and they won’t last long! Of course, these are spendy, but if you’re a lady with full calves, you know that good ones are hard to come by so consider them a long-term investment piece.

Are you already thinking about a dress you want to transition into fall? I’ve got another one or two I’m gonna work on and I’ll likely post those over on Instagram. So if you don’t already follow me there, I’d love to have you join in on the fun.

Hugs,