4 Chic Summer-to-Fall Outfits to Help You Transition Your Wardrobe

In this style guide, I’m going to show you some transitional summer to fall outfits. I am a big fan of fall: pumpkin spiced lattes, pumpkin patches, and don’t even get me started on Halloween! Of course, I also love fall fashion.


In this tutorial, I'll show you some of my favorite summer-to-fall transition outfits, how to turn a summer dress into a fall dress, what you can wear in that awkward period between summer and fall. Let's get started!


Summer to fall outfit 1

1. How to wear a summer skirt in the fall

Starting with the summer version, I went with a mustard printed floral skirt and paired it with a graphic white tee, flat sparkly sandals, and a small wicker bag. This outfit screams summer.


I transformed it into a more fall-appropriate outfit by switching out the graphic tee for a knit sweater. I wanted to keep the same color tones as the summer outfit, so I went with a sweater in a cream/off-white color. Knit sweaters are a key piece for the fall.


The next thing I switched out is the sandals; I went with a pair of ankle boots instead. These boots are perfect for the fall - they’re super lightweight, and I feel that they match any outfit.

Summer to fall outfit 2

2. How to wear shorts in the fall

The summer outfit here is a pair of green paper bag shorts with a black off-the-shoulder top.


I added a chunky gold necklace as an accessory, and for shoes, I have on a pair of open-toed wedges that have a nice snake print. The bag is a small tote with a fun wooden handle.


Now, we’re going to go ahead and transform it into something that is more fall-appropriate. I’m going to keep the top and the shorts, but I’m going to add elements to it.


The first thing I’ve added is a long cardigan; cardigans are essential for the fall. They’re an extra layer that you can throw over, and they can make anything fall-appropriate. This one has a nice color block scheme going on, and it's also lightweight, so it isn’t going to make you super hot. It’s a great transition piece for that in-between weather.

Summer to fall outfit 3

3. How to wear a summer dress in the fall

For the summer version, I have a blue denim dress paired with a pair of mules in a very bright coral color. These shoes are definitely made for the summer. To accessorize, I have a small wicker bag.


This is a super summery outfit from head to toe, and now we’re going to be taking it from summer to fall.


I’m going to keep the denim dress, and I’m going to throw a cardigan over it. Adding a cardigan changes the look from summer to fall instantly. This one is a different type of cardigan, it is more of a knit material, and it’s also shorter.


For the shoes, I’ve swapped out the mules, which are definitely summer shoes, and I’ve added a pair of very chic red ankle booties. I wanted to keep the look very simple and clean.

Summer to fall outfit 4

4. How to wear a romper in the fall

In the summer look, I’m wearing a green romper paired with a pair of open-toed wedges. Wedges are essential for summer, so this makes it a perfect summer outfit. To accessorize, I went for a small color block bag.


A romper is quite easy to transform from summer to fall because you can layer underneath it. For the fall look, I added a printed blouse underneath. You could just go for a regular black long sleeve top, which would also work, but I wanted to take it up a notch. The blouse instantly changes the romper from one season to the next.


For the shoes, I switched out the wedges for over-the-knee boots. Over-the-knee boots are my gem; I absolutely love them! I feel like they pair with anything, and they’re great with this romper to cover up a little skin in the fall.


The next element that I’ve added that definitely gives this outfit a fall touch is a black wide-brim hat. These types of hats are perfect for the fall. I have them in lots of different colors, but this black one is a go-to accessory for me, and it matches so perfectly with this outfit. Lastly, I switched out the colored bag for a small black bag.


Summer to fall outfits

There you have it: four summer to fall transition outfits. With just a few tweaks and switches here and there, you can seamlessly and instantly change an outfit from one season to the next. Which was your favorite look? Let me know in the comments below.

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