How to Transition a Summer Dress into Fall

Today I’m continuing to talk about getting more mileage out of our summer wardrobes and showing you how to transition a summer dress into fall.

My No Buy July and August are over and I’ve actually started buying a few (or more) new pieces to add to my fall wardrobe. I’ll talk more about that in another post, but mostly, I’m updating my denim collection, and I’m adding a few staples pieces to complete outfits.

But, I don’t know about you, I don’t have the budget to reinvent my wardrobe every season. Plus, I love lots of things in my closet, especially my summer dresses, and I’d like to wear them a little longer.

Don't put your summer dresses away when the weather starts to cool down. Booties and jean jackets can transform them into the perfect fall outfit. #midsize #midsizefalloutfit #falloutfitinspiration #transitionalfashion #plussize #fashionforwomenover50 #longgrayhairstyles

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YOUR SUMMER DRESS

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

THE PERFECT INGREDIENTS TO TRANSTION A SUMMER DRESS INTO FALL

Jean Jacket

Don't put your summer dresses away when the weather starts to cool down. Booties and jean jackets can transform them into the perfect fall outfit. #midsize #midsizefalloutfit #falloutfitinspiration #transitionalfashion #plussize #fashionforwomenover50 #longgrayhairstyles

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

Don't put your summer dresses away when the weather starts to cool down. Booties and jean jackets can transform them into the perfect fall outfit. #midsize #midsizefalloutfit #falloutfitinspiration #transitionalfashion #plussize #fashionforwomenover50 #longgrayhairstyles

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.

Don't put your summer dresses away when the weather starts to cool down. Booties and jean jackets can transform them into the perfect fall outfit. #midsize #midsizefalloutfit #falloutfitinspiration #transitionalfashion #plussize #fashionforwomenover50 #longgrayhairstyles

SWEATERS & BOOTS

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

Cardigan

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

Boots

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.

DO YOU HAVE ONE IN MIND?

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,


SHOP THIS LOOK

Don't put your summer dresses away when the weather starts to cool down. Booties and jean jackets can transform them into the perfect fall outfit. #midsize #midsizefalloutfit #falloutfitinspiration #transitionalfashion #plussize #fashionforwomenover50 #longgrayhairstyles
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7 Comments

  1. Jacki Salinas
    /

    You’re so cute! And I love your attitude/sauciness!

  2. I think we could shop each other’s closets and have lots of fun! I’m only a hop, skip, and a really big jump away! Yes, yes, yes to the cropped jean jackets! I have a couple of jean jackets from J Jill in petite that are almost perfect. They could be a skosh shorter, though. And, while I like booties (so much), what I don’t like is the way a bootie in a color not my leg color (tights are my friends) shortens and widens my legs. They are short and wide enough so I don’t need any help! Love all of these looks and suggestions!

    • Paula
      Author
      /

      Well hey there Marsha (in the middle) 😘. You should look at my post on booties. It was a fave changer for me when I realized why I didn’t like booties. Now I generally prefer them over tall boots.

      Hugs,
      Paula

  3. Jan
    /

    All of these outfits are adorable.. but that dress….
    Love ❤️

  4. I have several dresses that I like to do this with: I alternate denim jackets with them and like you add a belt or not depending on the day. I have a couple booties that I think work really well with dresses, one of my favorite pairs is very similar to yours: beige with a low shaft. This dress is a winner and you look wonderful in this pictures!
    http://www.chezmireillefashiontravelmom.com

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