15+ Casual Dress Outfits for Fall We're Dying to Try.

There are two kinds of people: those who mourn for the season that has passed and those who get super excited for the season ahead.

But, since fall is already here. I see no reason why we cannot embrace it zipping hot coffee, wearing our cozy sweaters, and sophisticated scarfs.

Transitioning seasons should be exciting for every single one of us, especially because we get to wear those clothes that looked suffocating during summer but undeniably classy, and stylish. The dramatic wardrobe awaits, and it is time once and for all to make a dramatic entrance into a new season wearing unexpected pieces.

I mean, let’s face it: everyone expects you to wear skinny jeans and ankle boots. And while that is such a cute outfit, everyone should see that one coming. Fall lasts 91 days.  Are you going to wear leggings and jeans every single day for 91 days? The answer should be No way!!. 

Correct me if I am wrong. You are one of those girls that make emotional purchases once they have spotted a piece of clothing that has the potential to create THE perfect outfit. So I am sure that you have the mandatory LBD (little black dress) in your wardrobe, a few skirts and maxi skirts, and some dresses that are not summer-exclusive.

So it is time to use your creativity muscle and show the world that you are more than jeans, leggings, and sweatpants. And, even though they are the logical option, you need to know how to diversify your outfits.

I know it can be a little challenging, but that’s what we are here for. Let us show you a few ideas on how to wear a dress in the fall. Don’t forget to put on some statement jewelry that blends in perfectly with your outfit. You’ll look bold but stylish, cozy, and classy.

Fall Casual Outfit #1: Dress + Over-the-knee boots.

Wearing heeled over-the-knee boots, it’s probably outside of the ‘casual’ zone. They look classy and stylish, especially wearing them with a beige trench-coat. But it’s Ok! So what if you are a little too overdress they can’t take your shine away. You are simply breathtaking.


Alternatively, you can wear a sweater-dress with your over-the-knee boots, they will look great with those low-heeled boots:


Fall Casual Outfit #2: Leopard Dress + Knitted Sweater

Animal prints are the new neutral. They were everywhere in the summer outfits. Just because is a dress doesn’t mean that you should put it away once the fall has arrived. Just put on some knitted sweater and some boots (or even sneakers), and you’ll be set to go.



Fall Casual Outfit #3: Floral Maxi-Dress + Over-the-knee boots.

Who said floral maxi-dresses (even maxi-skirts) were only meant for the summer? Especially if they have earthly or cold colors. Put on your floral maxi-dress, your jeans jacket, your combat boots and you’ll have an unexpected but very fall-appropriate outfit


Maxi dresses with earthly colors will look absolutely flawless in fall. Some ankle boots are the perfect addition, with a matching belt that creates a form-fitting outfit.


Fall Casual Outfit #4: Midi-Dress + Sweater.

The same midi-dress that made turn heads while wearing them with stilettos can create a casual fall outfit with some cute and stylish mules. They are perfect for transitional outfits, and casual Friday outfits. Don’t forget to wear a chunky sweater.


A printed pencil skirt goes perfectly with a knitted sweater. This style will keep you cute and cozy at the same time. Sneakers will go perfectly with this outfit.


Fall Casual Outfit #5: Dress + Chunky Knitts.

For some reason, every time I think of Chunky Knitted Sweaters, I picture them match with jeans or leggings. Don't be like me. Remember: use your creativity muscle. Wearing a chunky knitted sweater on top of a dress and combat boots it’s a bold choice. Just try it!

Also, you can wear a pleated maxi skirt with a chunky knitted sweater on top. The belt offers a stylish detail to the outfit.


Also, you can wear a pleated maxi skirt with a chunky knitted sweater on top. The belt offers a stylish detail to the outfit.


Fall Casual Outfit #6: Maxi-dress (skirt) + Sweatshirt.

If you want an even more casual style sweatshirt is a good alternative.  Wearing a sweatshirt has a distinct beauty of chaos, and matching them with combat boots seems like a bold option.


Remember your leopard printed maxi-dress (or skirt) that we mentioned earlier. While this trend is suited amazingly with summer silhouettes and fabrics, it is going as big for fall fashion. Add as a sweatshirt and sneakers.


Fall Casual Outfit #7: Printed Dress + Belt + Boots.

Vintage pieces are back, printed dresses included: they simply seem to outlive trends. So, as far as I am concerned the more dresses you have the better. You can always update past trends with new accessories (including belts) , shoes, and other pieces of clothing.

The latest trends seem to have many flowy dresses. You can add a belt to create a form-fitting outfit. A mini-dress with tall boots will update a classic outfit.


Heeled combat boots with a matching belt, create also a stylish outfit.


Fall Casual Outfit #8: Sweater Dress + Combat Boots.

Over-the-knee boots create a dressy stylish outfit, but they aren’t the only option. Wearing combat boots also create a cool style, and will make you step out of your conventional style box. Combat boots are a must-have for the season. You can try bright colors:

Or you can follow a fall color palette with more neutral, earthly colors:


Now there is no excuse only jeans and leggings all the fall. Please make us proud and show the world that you can style a dress in fall flawlessly. If you liked our post please share!

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