Hi there! It’s getting to be the time of year when I start to think about how long I can wear my summer dresses into the quickly approaching fall season. The warm weather is still here, but I’m ready to add in a few fall touches to my looks! I only pick up a couple of dresses each summer, so it makes the summer to fall transition fun. Late summer and early fall are the best times of the year to style these dresses a little differently. I love how you can get more outfits from the same dress.
I use affiliate links throughout this blog post, which means I might make a commission if you use my link and then make a purchase. This commission comes at no cost to you.
How To Wear Summer Dresses In Fall
There are a lot of ways to get fall looks from your summer dresses. First, and one of the easiest, is to shop your own closet for fall essentials that go with these dresses. Think button ups, lightweight jackets, suede accessories, and loafers that you already own. Plus, you’ll see where you might have a few gaps in your fall wardrobe!
A button up that you love will go a long way to bringing your summer dresses into your fall outfit rotation. They’re the perfect extra layer, and it’s so simple to just layer one over your dresses. You can also make other small changes like trading your sandals or espadrilles for loafers or ballet flats. Okay, here are some outfit ideas with these tips and others in mind as we transition our summer wardrobe to fall.
How to Transition Summer Dresses to Fall
Summer Dress With An Oversized Button Up
Your favorite lightweight and flowy summer dress will look just as nice with a button up over it as it does by itself. This is my go-to oversize button up. It’s not so oversized that you can’t also tuck it in with your jeans, though!
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. I’m looking forward to wearing this outfit with these loafers soon. The dresses below are similar to mine and also by J.Crew. If you’re on the east coast or anywhere else where it stays warm until October, these dresses are perfect for hot summer days that turn into warm early fall days.
Summer Dress With A Blazer Or Denim Jacket
Another way you can transition a summer dress to fall is by adding a blazer over your dress. I went for a linen blazer here. This outfit is perfect to wear on an early fall vacation too. I loved wearing this look to Maine! Denim jackets are another style of outerwear you can wear over your summer dress, especially once the morning and nights feel cooler.
Here are a few denim jackets and tops I’d layer over a summer dress. I have and love the last one. You can see it on me here.
Olive Green Linen Dress: The Perfect Summer To Fall Color
I had a return to do and ended up doing some browsing when I bought this dress from Everlane last summer. A linen shirtdress is a classic dress that you’ll wear forever. Aritzia makes one that looks so similar to this green, and I linked it below. Olive green 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.
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, go for colors that don’t give off as much of a summer feeling. The green midi dress from the outfit above is perfect to achieve that fall feeling in an outfit. You can also add in suede accessories with your linen pieces or wear shoes that feel more like fall – like slingbacks – but still keep your feet cool. These woven leather flats do the same thing. They’re so comfortable!
You can also go for ultra lightweight layers. 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.
Hill House Nap Dress With Loafers Or Booties
If you think you need to pack away your favorite summer Hill House dress, don’t do it just yet! You can easily wear this dress into the fall. Click here to see a video I put together on how to style a nap dress throughout the year. These dresses work perfectly with long sleeves, whether you wear a button up or denim jacket. The exact dress I’m wearing is actually perfect to wear into the fall because it has earth tones. That means it’s easy to pair with neutral loafers, blazers, boots, and denim. You can even style a turtleneck under your nap dress!
Hill House Nap Dress With Cotton Sweater
But, you can still get more from a nap dress that looks like summer, too. I included a photo below of how I like to tie my cotton fall sweaters around my waist. It’s a cute accessory, but it can also be practical for the fall. You can swap your shoes to help with the fall feel too. Once it gets cooler, I’ll put my sandals away and wear my loafers or ballet flats. This particular dress is gingham, so I wouldn’t wear it too far past September as gingham is really a summer pattern. But, this is one way to style it in the early fall!
Maxi Dress With A Button Up
This maxi dress was one of my favorite purchases this summer, and I’m planning to wear it in the fall with a cropped button up. You can see how it looks below with and without a little layer. I sized down to an XS in this button up, and I’m wearing a size small in the dress. I’d size down in both if you’re between sizes.
How To Wear Loafers With A Summer Dress
Do you ever wonder how in the world to style loafers with a summer dress? Don’t overthink it! It’s super easy and you’ll be so comfortable in these shoes. The pair I’m wearing below are a favorite from Sezane, and I also love these Sam Edelman loafers. I live in these in the fall and spring! They both come in other colors.
Linen Midi Dress With Leather Jacket
A linen dress is always one of my most worn pieces all summer. I go for a midi dress because they’re always the perfect length to play with my busy toddler. Extra layers that you can throw on in the fall are golden pieces in your wardrobe – they make getting dressed easy when you’re between seasons. A leather jacket is one of those layers!
Floral Sleeveless Dress With A Lightweight Layer
Okay, this nap dress is back for a specific outfit idea for anyone who is going to back to school events or meeting teachers. I love how understated this floral dress is. It’s really 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! It will look really nice with loafers, mesh ballet flats, or sneakers. It’s the type of dress you can wear with any shoe. Shop the outfit here.
Black Mini Dress With Loafers
Whether you have a short sleeve mini dress or a long sleeve mini dress, a black dress is the perfect summer to fall option. First of all, being that the dress is black, it doesn’t scream summer like a hot pink dress would. You can easily wear a black mini dress all 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. You can wear a black mini dress (I love this one) with loafers, add a suede belt and bag, or tie a denim shirt or sweater around your waist to add even more of a fall vibe.
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? Did you find a helpful tip on how to transition your summer dresses into the fall so you can wear them longer? Let me know what you think or if you have any tips! Don’t forget to sign up for my email list!
