How To Make A Summer Dress Work For Fall

Sezane Boheme Dress, J.Crew Woven bucket bag, Paris Texas crocodile-effect knee-high Boots, Madewell The Jean Jacket
Shop the Dress | Jacket | Boots | Bag

Attainable, functional, and versatile are all words that can be used to describe my fashion sense. That’s why I absolutely love comfortable and versatile Summer dresses that, with a little accessorizing, can easily become ideal Fall wardrobe ensembles

With a little creative styling, there are tons of Summer dresses that you can update and wear throughout the Fall season. This can not only save you some money, preventing the need to buy new, Fall dresses. But it can also fulfill your desire to live a more sustainable lifestyle. While I love snagging pieces from new collections, I’m not a huge fan of one-and-done fashion. 

So, if you’re in search of a little Summer to Fall fashion inspiration, you’ve come to the right place. While I’m not a declared fashion blogger, I do have a few practical and creative wardrobe ideas that can help make your transition into the Fall season a bit more seamless. 

Let’s dive right into my top Summer-Fall transitional dresses! 

How To Make A Summer Dress Work For Fall

J.Crew Woven bucket bag

How To Make A Summer Dress Work For Fall

How To Make A Summer Dress Work For Fall

J.Crew Slip Dress

There’s nothing like having a dress that highlights your curves in all the right places, but looks super delicate and dainty at the same time. That’s exactly what this slip dress does. It falls just below the knees and is made of a durable cotton fabric, making it the perfect Summer to Fall transition piece. 

What I really love most about this dress is how versatile it is. You can pair it with flats, heels, or lace up white sneakers. You can add a variety of layers, like a jean jacket, a leather jacket, a cardigan, or even a blazer. Or, you can even wear this slip dress overtop a cute short- or long-sleeve tee. So options, so many opportunities to show off your style. 

Tie-Strap Babydoll Midaxi Dress

This one comes straight from my top resort dress picks. Although the base color of this dress is off-white, the darker florals make it a good pick for that in-between Summer-Fall weather. Again, the super soft fabric and longer length provide just enough warmth for the Fall season, but not too much that those warmer afternoons become unbearable. My favorite part? The adjustable shoulder straps. They make finding that perfect fit around the bust so much easier. 

I love that this dress pairs perfectly with white sneakers or ankle boots. Although you could also rock some adorable flats. Now, since it’s Fall, you’ll need a little coverage. I recommend grabbing one of these denim jackets. Denim jackets are great for providing just enough warmth and protecting your skin from those harsher Fall winds. If you like this dress, definitely check out this one, too!

Midnight Leaves Mini Dress 

The Midnight Leaves Mini Dress from Farm Rio combines all the best Summer and Fall vibes into one adorable dress. The colors, the print, the fit, the attention to detail from top to bottom – everything about this dress is just flawless. I actually own this dress and recently wore it for a big shoot that’s debuting in October. So if you’re undecided about this one, check back soon to see this dress in action! You can also check out more of my Farm Rio faves, here

Now, let’s talk about how to style a dress that’s already giving so much. Since the dress itself is a statement piece, I recommend going with neutral accessories. This dress was made for gold jewelry, and I think these OMA Gold Hoops are the perfect addition. Then, black heels, a matching black handbag, and some sheer black tights (in case of colder weather) should do the trick. 

Freya Midi Dress 

Even though this dress is from a Summer Collection, the pink and brown floral design (and the fact that it’s long-sleeve) just makes this dress feel like Fall. Plus, midi dresses are the ideal length for the Fall season. Since they’re not full length, they don’t allow you to get too hot on warmer days. But, just in case you encounter some chillier weather, they still provide plenty of coverage for the bare legs. 

In addition to the cute print, the tie-front is what really makes this dress pop. The tie is adjustable, allowing you to adjust how much of your midriff you want to show off each time. If Fall weather in your area is still generally warm, I recommend grabbing some strappy flats or these mules. You could also totally elevate this look with some Fall-inspired knee-high brown boots.

Lace-Up Puff Sleeve Midi Dress 

Here’s another Summer Midi dress that can definitely double a Fall favorite. If you’re ready to channel all the cutest cottage-core vibes, this is the one for you. The light flowy fabric, puff sleeves, and tie-front accent all work together to highlight your shape and accentuate those curves. Especially if you add a thin brown belt. 

In the Summer, I would pair this dress with a straw hat and sandals, but for Fall I’m ditching the Summer wear for ankle boots (I especially like the Ivory in this style) and sneakers. Even dressed down, this dress is perfect for a day on the town or a night out with friends. Fall in the Mid-Atlantic doesn’t get too cold until after October, but just in case, I would grab an extra layer when I hit the town after dark. 

Sezane Leana Dress

This Sezane Leana dress comes in five different colors, one of which is called “fall is blooming”. How fitting for our topic today? Anyway, this dress is best described as a short dress with long sleeves, making it ideal for those days that are not too hot, but not too cold either. The accents I like the most are the gold snap buttons and the collar. These details really elevate the dress, especially if you’re going for a more dressed-up or formal look. 

On an ideal Fall day with warm weather, you won’t need any extra layers, and you might even be able to get away with some cute sandals. But, for those of you that like to switch over closed toed shoes after Labor day, I recommend some knee-high boots like these. Oh, and if you’re a big Sezane fan like me, I think you’ll really love the Ninon and the Lauretta styles by Sezane as well.

What are your favorite Summer to Fall transitional pieces? 

Share your ideas with the community in the comments below; I can’t wait to see all your answers! For more fashion inspo, definitely click on over to my LTK shop. And for more on all things travel, style, lifestyle, and beauty, head on over to my blog, or follow my adventures on Instagram

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