Hi there! Happy Friday! It’s getting to be the time of the year when I start to think about how long I can wear my summer dresses into the quickly approaching fall season. We’re on the other side of the latest heatwave, and I’m hoping it was the last one we’ll see this summer. Anyway, I only get a few dresses each summer, so I wear them a lot. Late summer and early fall are the best times of the year to style them a little differently so you can get more outfits from the same dress.
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How To Wear Summer Dresses In Fall
There are a lot of ways to get fall looks from your summer dresses. One of the easiest is to shop your own closet for fall essentials that go with these dresses. Plus, you’ll see where you might have a few gaps in your fall wardrobe! Okay, here’s a roundup of summer dress outfits that you can wear this fall. Plus, a few style tips along the way.
How to Transition Summer Dresses to Fall
Summer Dress With An Oversized Button Up
I recently picked up this midi dress and I just keep turning to it. It’s incredibly lightweight, comfortable, and flowy. If you’re on the east coast or anywhere else where it stays warm until October, this dress is perfect for hot summer days that turn into warm early fall days. Anyway, it’s simple to layer a button up over a sleeveless dress like this for a fall vibe. I actually wear this look throughout the summer because I like to protect my arms from the sun, but this look is perfect for early fall, especially with closed toe shoes.
Okay, I had a hard time choosing between the dress that I bought and the matching set version. They both come in several colors. So, I’m linking all of the options below because I’ve seen them in store and they all look nice. If you’re looking at the green dress and matching set, I highly recommend the matching set because that particular green is just so beautiful. It’s also the perfect shade for fall.
I also linked below the pieces I would use to make this outfit look and feel like fall, including the exact shoes and bag I’m wearing in the photos above. I’m looking forward to wearing this outfit with loafers soon too. If you’re looking for a pair of square frame sunglasses, I love the pair I’m wearing.
Summer Dress With A Blazer Or Denim Jacket
I created a reel with outfit ideas for my dress because I wanted to show how versatile it is for a dress that seems so summery. The other way you can wear this dress into fall is by adding a blazer over the dress. Click here to see how I styled it with a tan blazer (shop similar here) and the same shoes I’m wearing above. I also love the idea of wearing a denim jacket over it. This dress is perfect for the weekend or a vacation!
Olive Green Linen Dress: The Perfect Summer To Fall Color
I had a return to do the other day and did a little browsing while I was out. I noticed this dress that I’d seen online and ended up loving it in person. It’s really beautiful and so well made! The olive green color is perfect to wear into fall with leather accessories. I styled it below for work or a nice event, but you can wear this with slides or sneakers too.
Be sure to size down in this dress. I’m wearing a 0, and I’m normally a 2 or 4 in dresses in most companies. Shop my exact Celine belt here.
How To Style A Summer Dress For Fall In A Hot Climate
Do you live somewhere like Florida, where it never truly gets cold like it does further north? If you still want to make your summer outfits look a little more like fall, try a lightweight layer. This vest is my favorite lightweight layer for summer temperatures. It’s neutral, so you’ll be able to wear it throughout the year – it’s truly an essential! You can see it on me here.
You can also opt for colors that don’t give off as much of a summer feeling. This green midi dress is a great option to achieve that fall feeling in an outfit. You can also opt for slingbacks – this pair looks very similar to the pair I’m wearing below. They’re a nice shoe for warm weather, but they still keep your feet feeling cool. I also included a black mini dress later in this blog post that’s another good option for dressing for fall in a hot climate.
Hill House Nap Dress With Loafers Or Booties
If you think you need to pack away your favorite Hill House dress, don’t do it just yet! You can easily wear this dress into the fall.
This particular nap dress has the most beautiful pattern and the colors are also gorgeous. I styled it a couple of ways below. The oversized denim jacket is a little edgy and it mixes that vibe nicely with the super feminine dress. It’s the perfect combination. I left half of the denim jacket out of the photo so you could see them together. I would wear the jacket open. The booties I included in the second outfit are super comfortable and a great price! You can see the boots on me here. PS, if you want to see this style of dress on me styled for fall, click here.
Floral Sleeveless Dress With A Lightweight Layer
This floral dress is the perfect piece to wear into fall because of the colors and the length. You can easily layer it with a blazer, a button up, a cardigan, or a lady jacket since the dress is sleeveless! I currently have this one in my cart. It will look really nice with black loafers, mesh ballet flats, or sneakers. It’s the type of dress you can wear with any shoe.
I styled this dress with two different layers I would wear it with – the first one is probably my favorite. It’s a relaxed fit lady jacket in sweater material. Once it’s colder, you can layer the dress with a cashmere crewneck sweater and it will look like a skirt! Add a belt if you think it needs a little shape! Or, go for a leather jacket. There are tons of options with this dress style. I’ve been happy with all of my recent Madewell purchases recently, so I’m excited to see another cute dress!
How to Wear A Slip Dress This Fall
Slip dresses don’t get enough credit for being versatile. I’ve worn the same slip dress to a wedding, to a casual dinner with a t-shirt under or over the dress, and with a denim jacket and sneakers to run errands. You can basically add a layer or swap your shoes to make this style of dress ready for fall – and for different types of occasions. As we get later into fall, sweaters and cardigans work perfectly over a slip dress. This type of outfit is cozy and chic. I love the maxi length of this slip dress for cooler days!
How to Wear A Slip Dress For Work In The Fall
Have you ever worn your slip dress to work? They look really nice with a turtleneck underneath or just a blazer over them depending on the neckline. You can also wear them with a cardigan or crewneck sweater over the top. Basically, you can treat the dress like a skirt. I styled it here with a crewneck cashmere sweater that I own and have worn with a slip dress. I love the denim jacket for a casual office Friday or if you’re in a casual work environment where jean jackets are allowed. Otherwise, go for a blazer! I recently purchased this one.
Linen Dress With Leather Jacket
This linen dress is one of my most worn pieces all summer. It’s the perfect length to play with my busy toddler, I love the off white color (it also comes in black), and it has enough shape that I don’t feel like I’m wearing a bag. Plus, it’s versatile. I wear it by itself or add a button up over it right now. This fall, I’m looking forward to wearing it with a leather jacket, which is how I styled it below. Size down in this dress! I’m wearing a 0, and I’m normally a 2 or 4 in J.Crew dresses (for example).
Black Mini Dress With Loafers
My black shirtdress is pretty decisively a summer dress since it’s not really possible to add layers over it. But, you can definitely wear it into early fall if it’s warm where you are. It will certainly be warm enough here in DC to wear this well into September and even October. Plus, go for a closed toe shoe like I did here. I’m most looking forward to styling this dress with loafers this fall!
Suede Jacket Over A Summer Dress
Suede jackets are a classic, and they’re already everywhere for fall. I love this one (you can see it on me here). You can layer a suede jacket over a dress to take the look into fall. I love to pair this type of outfit with loafers, ballet flats, or slingbacks!
What’s your favorite way to wear your summer dresses into fall? Let me know what you think or if you have any tips!
