We’ll Still Be Wearing This Fall Dress Trend in 5 Years—Shop My 25 Favorites

Right now I’m transitioning everything in my wardrobe over for fall and winter. I’ve just swapped out my sandals for boots and pulled out my chunky knit sweaters from the back of my closet. And with all this closet reorganization comes another category: dresses. Yep, you guessed it: I’ve just put away my light sundresses until next spring and replacing them with fall-ready long sleeve midi dresses.

There are dress trends and then there are dresses that are classic enough to be categorized as a fall staple. IMO, midi dresses with long sleeves fall into the latter category because the style is one that just never seems to quit. No matter what the dress trends du jour are, I’m confident that there will always be a spot in my closet for a few of these midi-length numbers.

Ready to dive into this roundup of fall dresses you can wear now and own for years to come? Scroll down to shop my favorites that I’m already envisioning with other seasonal staples like boots and jackets.

We did it. We made the perfect fall dress.

Ganni does it again.

Knit dress are trending hard right now, and I love that the button detail makes this stand out.

So many cool girls will wear this dress with boots in the fall and winter.

Now let’s hear a little commotion for the back of the dress.

Simple, but so cool.

If you’re going for that romantic grunge look this fall, pair this pretty lace number with chunky combat boots for a cool look.

This print!

For obvious reasons, I can’t stop thinking about this dress.

Speaking of knit dresses, this is leaving me speechless.

The back is even prettier if you can believe it.

I’m crushing on this tie-up sleeve detail.

Because fun florals will always be a mood.

A seasonless staple.

Up next, 5 trendy basics women over 50 are indulging in this fall.

The kind of dress that looks just as good with sneakers as it would with leather boots or straps sandals.

I’m speechless.

Why, yes, this does double as a house dress I’m so glad you asked.

How to make an impression on your Zoom calls 101.

I had to blink a few times to make sure I read the price correctly because I can’t believe a dress with this much personality is under $30.

I could stare at this print all day.

Now that’s a creative neckline.

This print!

This silhouette, though.

The name Parisian nights says it all.

This print lends itself well to wearing in the spring, too.

The kind of throw-on dress I always wish I had more of in my closet.

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