The Best Fall Dresses Inspired By Italian Style 

Whether you’ve started looking into your closet for fall dresses or shopping for new ones, I’m here to remind you of all the chic and timeless options worth having this season.

This is not about wearing your Summer dresses under a blazer. I have plenty of guides that do exactly that.

These are dresses built to shine this time of the year (though a few extra layers will easily carry them into winter). 

Curious? Let’s get into it.

PS: This post includes affiliate links. If you click and purchase, I may receive a small commission at no extra cost to you. I only recommend products I have or would personally buy.

Fall Dress 1: The Fawn Dress

This is the only dress option I am going to suggest that’s appropriate all year round, so if you already have it, you can keep wearing it. I almost always refer to it as the classic Max Mara beige dress. However, the actual color name is fawn – a shade in between a dark beige and a light tan.

A long sleeve midi A line shirt dress is my favorite silhouette when it comes to this color, but I have also found a beautiful long sleeved wrap dress in that same shade.

Who can wear this: 

Fawn is best suited to Autumns (that is women with that color season). However, Springs might be able to pull this off.

Don’t know your color season?
Read this to find out: Simplified Color Analysis For Clothes + Steps To Do Yours

How to style it:

How you style it really depends on the occasion and time of day, but also the exact time of the year and weather (is it a warm or cold fall?).

• Early fall: wear it with sandals.
• Fall trip: style it with tan loafers and an over the shoulder sweater. (see image)
• Fall office day: wear it with closed pumps and a blazer over the shoulders. (see image)
• Cold fall: dress it up with tights, matching pumps, and a trench coat or a light coat.

The Tan or Cognac Dress

Unlike the beige dress, this is one of those dresses you mostly wear during the cosy season. It has the color of falling leaves and pumpkin spice, so if you were looking for a true fall dress color, it doesn’t get better than this one.

But, there is a but.. Not everyone can pull off this shade! Let’s talk about it.

Who can wear this: 

I am afraid option 2 is also one that’s best suited for Autumn and Spring seasons. So if you’re one of those, make sure you make the most of these colors (including tan, cognacs, rust, and caramels).

Inside my Shopmy collection, you’ll find plenty of options, from lighter tan cotton dresses to sweater and even leather and suede options.

How to style it:

I am giving you two examples.

The first is a linen dress, perfect for early fall. The idea is this: you’re going on an end of Summer trip, perhaps in Italy, in Europe, or something really charming, and you want a pretty dress that’s seasonal, comfortable, and layerable. Here’s how I’d style it for a day in Florence, or a day of sightseeing.

The second is the type of dress you can wear for different occasions. Here are a few ideas on how to wear it:

• Over a black knit or a white shirt with heeled pumps for work
• With minimal dressy accessories and a coat for date night
• Somewhere in between (which is the way I styled it below) – think a cosy day date, or a more luxurious weekend trip, where heels are ok.

The Dark Floral Print Dress

Those women who love wearing florals will love this fall dress idea, but don’t worry, it doesn’t have to be just flowers. It can be leaves, or abstract prints on a darker base color, ideally with a thicker fabric, but not essentially.

I say not essentially because the first dress I put in this collection is a silk one, and I think it’s the perfect transitional piece. The second one is also a light one, but that one comes with sleeves.

In terms of colors, black and navy blue bases are my favorite, and these are also better options if you’re a Spring and Winter.

Who can wear this: 

Since this dress is about the dark floral print, every color season can find the right one. Here are some recommendations to help you get started.

• Autumn: Brown bases are perfect for you.
• Spring: Brighter brown bases are better for you but you can also stick to navy options.
• Summer: Navy and greys are great.
• Winter: Go with a black or navy base with brighter jewel colored florals. If it’s still in stock, this one is exactly what suits us Winters.

How to style it:

I have picked my favorite two dresses and I’ve styled them for you below. The first is the dress that most suits my color season (Winter), and the second is one I really like but I can’t wear (this one suits Autumns).

The first example is perfect for a fall date night or event. You’re dressy but not too dressy, though you could swap the accessories to dress this up even more. It’s comfortable, cosy, and if you need it, you can wear tights (yes, even with slingbacks).

I chose to style the second for a day of sightseeing or perhaps a Saturday out for brunch and errands. I imagine a classy woman who loves looking good but being comfortable really loving this lightweight dress. If you swap the sneakers for black heels, you immediately have a dressy dinner outfit. It’s really that simple with this dress.

The Elevated Sweater Dress

Yes, even Italian women wear sweater dresses, but with a few rules in mind. The silhouette must be the right one for their body shape, and the fabric must be a high quality one, like a fine cashmere or silk cashmere blend, or a cosier wool option.

Think of it as the elevated sweater dress, the kind of dress you can pack on a fall trip and wear from morning to dinner, with the right accessories, of course. It’s not the sweater dress you wear to go lounge at a friend’s house, or bury under a coat for no one to see. And it’s definitely not one that’s badly pilling.

Who can wear this: 

Everyone, and this applies to colors and shapes. If you’re not an hourglass, don’t opt for the classic straight silhouette. Instead, an A line style will be much more flattering on you.

Inside the fall dresses collection you’ll see different options, including straight and A line, but also a few in between silhouettes.

How to style it:

You really have so many options with this one. You can dress it down and up easily, but it also depends on the color, the silhouette and the fabric. Let me show you two examples and explain what I mean.

The first one below, the one in burgundy, can be dressed down and up easily, because of the A line style, the richer color, and the fabric. The sheer layer on top also adds more interest.

Instead, the dark russet brown option looks more casual, and that’s mainly because of the fabric. Of course, if worn by the right body type, which in this case is mostly an hourglass or a really skinny woman, you might be able to dress this up but the fabric leans into casual. That’s why I went with the classic fall leather look.

PS: When I suggest the color season and the body types, I am just trying to help, because I want you to look good and feel your best, and avoid buying dresses that might not suit you. However, you decide what looks and feels best on you. So, take everything with a pinch of salt.

The Leather Dress

In case you didn’t know it, leather is really big in Italy during autumn. You can have fun looking at leather jacket outfit ideas here: How To Style A Black Leather Jacket Like An Italian Woman

But if a leather jacket feels too bold and masculine for you, or perhaps it’s just not cosy and sophisticated as you like your outfits to be, try a leather dress instead. Black and brown are great options, but you can also opt for stone or grey, among many other shades.

Inside the collection at the top of this post, you’ll find three brown ones and one black; hopefully, they’re still in stock.

Who can wear this: 

If you think a leather dress doesn’t fit your style, the right silhouette and color might totally change the way you feel about it. 

I’d say everyone, including older ladies, can wear a leather dress.

Best color for your season:

• Autumn: browns
• Spring: camels and mauve
• Summer: navy
• Winter: black

How to style it:

Don’t forget to scroll back up and look at the first leather dress I’ve styled for you under the tan dress section.

Next, I wanted to style this black leather dress the way I would wear it myself. I’d probably pick a different shoe and bag color, just because that shade doesn’t suit me, but it does suit the skintone in this picture.

This is the type of dress you wear with a shirt or a light knit in fall, or even under a cardigan or light trench. Then, you can wear it throughout Winter with warmer wool knits and thermals, and of course pop a coat on.

The Corduroy Dress

I am pretty sure that unless you love corduroy or you happen to come across it in a shop, this is the last fall dress idea that’s likely to come up for you. Yet, it’s perfect. It has a warm cosy vibe, and you might expect it to look more casual because of the fabric, but it doesn’t have to be that way. You can wear it on a casual date night, for work, or just to enjoy a fall weekend out and about.

Who can wear this: 

While autumns are the ones that will look best in this brown shade, you can look for a black corduroy dress, or a burgundy, green, and blue.

Personally, even though brown is not my best color, if it’s dark and bright like this one, I can pull it off.

How to style it:

I’d style it in a way that celebrates fall colors, with a little bit of cognac and olive.

Other ideas that come to my mind include:

• Under a trench coat with brown loafers or white sneakers
• Under a maroon coat with cognac shoes and bag
• Under a blue plaid coat with navy and brown accessories

The Suede Dress

There’s something very luscious about suede. You’ve likely experienced it if you own a bag or a pair of shoes, even if it’s faux suede. Imagine having a full on dress.

In the fall dresses collection you’ll find three sleeveless options in three beautiful autumnal colors. Which one would you wear?

Who can wear this: 

I am not going to repeat myself. Everyone can suit a suede dress, as long as you find the right color and silhouette. I have selected both shift style and A line dresses, which means there’s a style for you too. Find yours here.

In terms of colors, there’s also something for everyone.

• Autumn: rust or beige
• Winter: hudson green
• Spring: camel
• Summer: rust

How to style it:

I’ve picked the rust color as an example and styled it for a stylish corporate or business work day, although this could also be a great occasion outfit – think a fall christening or another daytime special event.

I kept the accessories close to the dress shade with a tan choice, and then brightened up the entire look with that cream blazer. Doesn’t it look gorgeous?

Classic Fall Winter Fabrics

My next fall dress suggestion is to find one that celebrates your favorite fall winter fabric. It could be plaid, tartan, tweed, herringbone, houndstooth, or a mix of any of those.

I’ve managed to find two gorgeous plaid options. You’ll find both in my ShopMy collection at the beginning of this post.

Who can wear this: 

Everyone, because you have so much room to find the one that works best for you. If you have any doubts, think about the fall blazers you already own and love, that suit your skin tone really well. You can find a dress similar to those.

For once, these blue toned plaid options suit Winter and Summers better than the other two color seasons. The darker one is best for us Winters, and the slaty blue one is better for Summers.

How to style it:

I am showing you how I’d style the darker version for a day in Venice. I don’t know why but this dress feels perfect for a romantic fall day in the floating city.

It’s really simple: pop it under a black overcoat or a trench coat and wear it with loafers, but rather than the usual black ones, I’d go for a lighter shade of blue. The stone bag is an option but you could play with black, cognac, green, and even mustard or a deep winter red.

A Dark Colored Dress

I’d like to leave you with one final dress idea and this is totally color based. Each season, and even sub-season will have its best color, so you need to find the dark color that suits you most.

The idea is to have a dark fall dress you can reach out for on a dressy date night, or if you have a sudden event to attend, and even a wedding.

Because black would definitely be my choice, followed by a bright burgundy or cherry red, I have chosen to style this black A line dress. Whichever color or style you choose, would likely go under a furry bolero like the one in my example. Of course, you can always swap it for a longer sleeved one or a full coat.

More Fall Outfit Ideas

I hope you found the perfect dress that’s missing from your fall wardrobe. Don’t forget all of the dresses I showed you are shoppable, if still in stock. My favorites are numbers 5, 9, 10, and 12.

For more seasonal outfit ideas, you can browse my other Italian fall style guides:

Fall Going Out Outfits: 6 Ideas Italian Women Swear By

11 Ways Italian Women Wear Comfy Fall Outfits

22 Italian-Style Layered Outfits For Fall

Fall Office Outfits That Aren’t Basic: The Milan Way

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A presto,
Alessia