Going out in fall just hits differently. Cooler evenings mean you can enjoy dinner, drinks, or an evening stroll without the summer heat getting in the way.
One question remains, though.
What do you wear?
The brief is simple: cosy fall going out outfits that range from elevated casual to feminine and dressy, keep you warm, and work beautifully with heels (whatever heel height feels comfortable for you).
The inspiration comes from Milan, where I spotted six clear ways Italian women approach fall date night dressing.
Depending on where you live, fall can feel more like late summer or the start of winter. For most of us, it’s somewhere in between.
This guide covers all of those situations. And if the temperature drops even more, simply add a coat before heading out.
Let’s get into it.
Table of Contents
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Wear A Leather Skirt
Come end of September, you’ll notice that leather comes out to play in Milan, but it’s not just leather jackets. In fact, to begin with, leather jackets might still be too warm for the transitioning weeks. That’s the perfect occasion to play with leather bottoms – both pants and skirts. But for this post, I’d like to highlight the leather skirt.
Leather skirts can look both edgy and feminine because of that fabric silhouette combination. That makes them the perfect piece to wear to go out in the evening. It gives you that extra femininity you’re likely seeking for that occasion, but doesn’t take away the modern and strong woman vibe that many of us (Italian women and non) love.
I suggest midi straight leg styles – like a roomier pencil skirt.
So what color leather skirt do you wear?
You decide. That decision should be based on your color preferences, but also your color season.
Read more about color season here:
Simplified Color Analysis For Clothes + Steps To Do Yours | Italy With An Italian
In my opinion, black is always the winner. It thicks all the boxes: it’s chic, dressy, edgy, and feminine.
But brown and maroon can work just as well.
How to style your leather skirt for date night?
I’d like to share 2 ways I spotted in Milan.
The first features a tan or other earthy fall color knit that’s both cosy and warm enough for your evening, also dressy.
The second consists in simply pairing your leather skirt with a white shirt tucked in. Of course, feel free to try it with different colors, but a white shirt is the absolute classic most of us have in our closet.
When it comes to shoes, both looks require heels. Closed pumps and slingbacks are my favorite options, but you can also make it work with minimal sandals.
Shop Leather Skirts
Wear Your Jeans With a White Shirt & Heels
Since I started with an outfit ideas that’s likely not everyone’s cup of tea, I’d like this second one to be more practical.
Nearly every woman has a pair of jeans they like, a white shirt, and a pair of heels. Of course, the fit and style of each of those pieces matter too. Nonetheless, this is a more attainable look, and also one that most of you going on a more casual night might prefer.
Don’t get me wrong, though.
Simpler outfits are often easier to mess up. Here’s why.
A simpler outfit needs to work harder to look really good.
The easiest way for it to do that is for the pieces to both fit you right and for them to be really nice quality.
Other than that, when it comes to styling your white shirt and jeans, you need to decide whether you want to go with a more classic or a more modern look.
Classic: tuck your shirt in, wear a belt or not, open a few buttons, roll up the sleeves or not, and finish the look with heels and accessories.
Modern: play with proportions, by combining straighter leg jeans with an oversized white tshirt. Roll up the sleeves, and open the first few buttons, so you show some extra skin. That extra skin helps balance the oversized look and adds femininity. Cropped jeans are a good ideas for that same reason. And that’s the same for strappy heels, though, you can also go with slingbacks or pumps.
Need A New White Shirt?
Don’t stop at a white shirt?
My other suggestion is to try black or darker colored feminine shirts and blouses. I particularly like the look of a sheer lacy one. You can wear it with a modest bralette underneath or a full on camisole, depending on what makes you feel most comfortable.
Doesn’t this blouse solve date night outfits?
Wear a Blazer Like a Top
You want to wear a blazer buttoned up with just lingerie or an invisible camisole. Of course, you need to be ok with not removing the blazer. If you think you’ll need to remove it, wear that invisible camisole I mentioned.
This creates a very sensual chic look. It’s the perfect example of that Italian saying that goes like this: your outfits, even the most feminine and sensual ones, should leave something to the imagination.
What that means is that it’s ok to wear something sensual and still look classy. You just need to find the balance that’s right for your body.
This helps you do that, because the closed blazer will have a low neckline that will showcase your gorgeous collarbone, and perhaps just a little cleavage. The important thing is that it looks tasteful.
How do you style a blazer worn this way?
I want to give you these two options:
- Wear it with jeans and heels. You can opt for straight leg jeans or even a slightly flared style like in the example below. Remember when I say straight leg it’s not fitted jeans, but a style that falls straight and doesn’t cling to your curves, sort of a more fitted mom jean.
- Wear a full suit this way. This works best with more modern oversized suits, because it makes the look feel more modern and youthful, less corporate. Imagine wearing the same suit for work, and then removing the shirt and swapping the shoes, accessories and jewellery for date night. This look would also work for a fall and winter wedding, spring too, but you’ll need a lighter suit color.
Shop Blazers Here
Wear Your Summer Midi Dresses & Skirts With A Blazer
Since number 3 was a little bit less straight forward, I want to come back to a date night outfit idea that’s easier to recreate.
We all have a lightweight Summer midi dress or skirt we love. Satin dresses and skirts work perfectly too.
All you have to do to make them fall evening appropriate is to pair them with a blazer and then cinch the blazer with a belt.
You can also skip the belt and just button the blazer.
If you’re trying this with a midi skirt, try wearing a matchy camisole. It can either match the skirt or the blazer.
Because this is clearly a transitioning outfit, the best shoes are heeled sandals or slingbacks. I’d suggest more minimal styles.
Keeping these outfits tonal, preferable with a maximum of two colors, will make them look even more sophisticated.
Mix Tailored Bottoms with Knitwear
So far, most of the outfit ideas felt very early fall or mild weather appropriate. These last two will start bringing in more warmth. I want to remind you again, that you can obviously increase your warmth by wearing thermals, tights, or layering a coat on top.
Here’s the idea: take your tailored pants and skirts, and wear them with a dressier knitwear. It can also be a very simple but high quality knitted piece that’s styled in a way to look dressier. There are so many videos online showing you how to wear a cardigan in a million ways…
If fall going out outfits are essential in your life, you might also want to invest in more feminine knitwear pieces. You can wear those on their own in fall, and then layer them under a coat during the colder months.
Below, I am showing you two examples with pants. But the same could work with a pencil skirt, or a midi A line skirt that’s slightly dressier.
The first is a black wide leg tailored pants styled with a very warm cardigan. If you keep the color palette dressy and add heels and nice jewellery, your outfit instantly feels dressier, especially because of the tailored pants.
The second features a dressier knit paired with wide leg satin pants.
Shop Dressy Knitwear
Play with Tights
We can’t talk about fall going out outfits for women without mentioning tights, especially since Italian style is at the core of our discussion.
Italians love socks for styling, and the same is true for Italian women and tights.
Here are three classic tights outfit ideas perfect for evenings out.
- An all black look with intricate black tights. In this case, the tights have a lace effect, but feel free to choose your favorite style. The woman is wearing them with a black blazer and a shorter black dress and black heels.
- An oversized blazer worn as a dress paired with playful feminine thighs. I think the blazer color pairing and polka dot tights couldn’t be more perfect to create a playful modern vintage look. Of course, you can also add matching shorts or a skirt or a shorter dress underneath the blazer.
- Finally, tights don’t have to come in intricate designs to look good. A simple sheer pair can create a very chic evening look, especially when paired with a tonal outfit and a nice pair of heels. I love how this outfit does that while playing with the height of the different pieces – a shorter blazer with the tonal skirt peeking out.
Playful Tights
More Fall Outfit Ideas
Did you find one or two looks that got you inspired?
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Since it’s clear you’re in that fall planning phase, I’d like to leave you with more fall outfit guides. These might inspire you for fall nights, work outfits, or anything in between. Have a look and see what you find.
15 Blue Jeans Outfits From Milan
Fall Office Outfits That Aren’t Basic
How To Style A Leather Jacket Like An Italian Woman
Chic Sweater Outfits Straight From Italy
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A presto,
Alessia
