Classy Shorts Outfits with an Italian Touch

If you are one of those women who doesn’t feel comfortable wearing shorts past your doorstep, you’re not alone.

Whether it’s because you don’t like your legs, or you think shorts outfits are too casual or not sophisticated enough, the truth is it all comes down to styling.

Styled well, they can look just as refined as any other piece in your wardrobe.

And the outfits I am about to show you—straight from the streets of Milan—prove exactly that.

Let’s have a look.

Elevate Your Shorts Outfits With A Blazer

This is the easiest way to dress up your shorts, and the best thing is that it works whether you are wearing flats or heels.

Here’s how to recreate this outfit formula:

1. chic A line shorts, not too tight and not too short
2. neutral silk camisole, tucked in to show the waist
3. blazer over the shoulder for that effortless in between seasons chic style

In terms of colors, this outfit works because it includes a pop of color and then it keeps all the rest neutral and fairly monochrome. Inverting the pop of color on top works just the same.

Keep It Casual Chic With A Modern White Shirt Blouse

Imagine swapping that white shirt blouse with a white tshirt. Can you see how that would make the outfit too casual and nothing special?

Copy this outfit formula:

1. Wear a pair of tailored shorts, even if shorter. The black dresses them up.
2. Wear a statement top, like this voluminous fun but equally timeless shirt.
3. The black and white adds to the classic vibe.
4. The casual sliders and cross body bag give it a youthful day time look that still looks curated.

Don’t Like Shorts? Try Longer Ones.

This one is for my lovely readers who say they don’t wear shorts outside the house.

Have you tried longer shorts?

While they are not for everyone, especially us petite women, they can look stunning if you’re taller.

They also give you the excuse to wear shorts for work.

Here’s how to recreate this outfit formula:

1. Choose a pair that has the perfect length for you – just above the knee is the safest option, but taller ladies can go slightly longer, and this is the perfect example.
2. You can keep the shorts color neutral; that will make it a more versatile piece in your Summer closet. But don’t be afraid to play with color; you can then pair it with more neutral pieces.
3. Tucking in the top is essential to create a more balanced silhouette.
4. Dress it up with heels, or opt for elegant sandals.

The Perfect Shorts Set Can Be Very Casual Chic

You can wear it to the airport, shopping, or to run errands. If it’s as comfortable as this one looks (satin or silk, but also cotton and linen) you will feel like wearing pajamas but the look channels the casual suit vibe. And this Summer it’s all about that!

Copy this outfit formula in 4 steps:

1. Choose a color that flatters you. Read my color analysis guide if you need help with that. This look shows you that colorful can still look sophisticated, but only when it’s the right color for you.
2. Layer a high quality tank top. I like the square neckline because it’s demure but also shows enough skin.
3. Style it with a small chic purse, unless you need that bigger tote for the airport. That can work too.
4. The shoes are going to be the piece that transform this outfit. Wear it with loafers, or Tods-style slip on, and you have a tasteful relaxed look. Swap them for heeled sandals and the outfit feels immediately dressier, still retaining that relaxed mood.

Nothing More Effortlessly Chic

I truly believe this. There’s nothing more chic than a simple monochrome outfit where all the pieces are well tailored, well fitting, and with quality fabrics. It’s even better when the accessories are also tonal. And this look fits that profile to a T.

If you are on the fence about wearing shorts with a more sophisticated style, I suggest you start with this look.

And if you don’t want shorts shorts, swap them for longer ones, but it keep it tonal.

Make it work this way:

1. Focus on the fit of your shorts.
2. Make sure each piece feels tailored and structured.
3. Add a heel, even if low.
4. Keep the purse small.
5. Dress it up with the accessories.

Classy Shorts With A Tank Top

Tank tops can feel quite casual, don’t they?

Well, you can easily change that by choosing a straighter shoulder cut, with a wider stap that covers more skin but it’s still sleeveless. And you can also swap the cheap looking ribbed fabric with a silk or linen, or anything that has that look.

This is what I mean:

Why this outfit feels classy:

1. The tasteful length of the shorts.
2. The modern straight line cut of the pieces.
3. It’s showing enough skin but not too much.
4. The accessories are dressy.
5. It’s tonal, and it also suit the woman’s skin color.

Denim Shorts Can Look Classy Too!

As an Italian, denim shorts are the last thing I would call classy. Yet, this outfit works, and I will explain why it does.

1. Firstly, it suits the woman’s body. I would consider these short shorts, but because of the taller lean legs, this still feels tasteful.
2. The straight leg and simple wash of the jeans give them a classic vibe.
3. The long sleeved feminine blouse dresses the outfit while keeping it casual.
4. The heeled sandals add to that femininity.
5. The belt give it that Italian touch that brings the outfit together because even a pair of denim shorts deserves a nice belt.
6. The neutral pop of color with the bag (tan is a classic neutral but it’s still a color when compared to the rest of the outfit) adds that unexpected element that draws the eye.

This outfit almost screams I dressed like that in 5 minutes and I love it. And that’s the result of a curated wardrobe.

Here’s How To Wear Shorts To The Office

I’ve already showed you an outfit that could work for the office in Summer. If you thought that was a little too creative, this one is perfect.

All black, brown bag, heeled pumps, paired with a shirt, and the shorts have a good length.

There’s nothing to think about here, other than these three things:

1. The shorts must fit as well as a pair of tailored pants.
2. Heels are recommended, but pointed flats can work as well.
3. Keep it monochrome.

A Shorts Outfit That Channels Italian Old Money

If you like the more Italian preppy style, the kind that always features a shirt and a sweater over the shoulders, you will love this one.

It’s the perfect outfit to go designer shopping, but you can make it work for many other occasions too. Imagine wearing this to meet your in laws! They’ll think you are pretty, chic and timeless.

With that said, you don’t need to be in your 20s or 30s to wear this outfit. It can work for older women too. Just adjust the length and the fit of the shorts to flatter your body.

Don’t worry, you can swap the heels for loafers, and still retain that quiet luxury vibe.

Very important: don’t underestimate the power of a well structured handheld bag. If you swap it for a crossbody or a tote, you will lose that dressy effect this piece brings to the look.

Never Thought Of Wearing A Suit With Shorts?

It works, doesn’t it.

It can work for the office in Spring and Summer.

It can work for a date night if you are the feminine type of woman who doesn’t need to wear a pretty outfit to feel good in her skin. Strong and powerful can be as feminine as a frilled blouse.

This can also be a no brainer for an event that has a smart casual code.

Can you see how those loafers dress it down? Yet, we could easily swap them for heeled sandals and immediately add a more feminine dressier element to this outfit.

Linen Shorts With Sleeveless Blazer

If you like the idea of wearing a set or a suit with shorts, here’s another way to do it.

This time we have a blazer vest, and a linen set. It’s perfect for the warmer months.

The fit here is oversized and cooler, and the tshirt supports that vibe.

But you could easily opt for a more fitted tailored set and wear the vest buttoned up as a top.

Vacation Mode: Classy Shorts Outside The City

All the outfits I have shared in this post are inspired by what Italian women wear in Milan, or in Rome and Florence, when they want to dress for the weather but also the city.

Well, I’d like to take a break from that and show you just one outfit for vacation to prove that shorts can look sophisticated even when you don’t over style them.

That shirt does it all! It adds that element of tailoring even for the beach. You can read more about that concept in my Tailored Style guide.

How To Wear Shorts In Between Seasons

This might be my favorite one. It’s simple, unique and timeless all at once.

There’s something about that pairing that I love so much: the green suede shorts, with the blue pin stripe shirt, and those rich dark brown accessories. It’s very quiet luxury but with a pop of green.

This might not be the color palette or fabric choice you gravitate towards in Summer, but it can work wonderfully as a Spring to Summer or Summer to Fall transition look.

That also holds for the last two outfits I am about to show you.

How To Wear Shorts To A Concert, But Make It Classy!

Could this be the elegant Italian version of a Coachella outfit?

I am not sure, as I have never been into that. You tell me!

One thing I can say is that looks like the perfect pretty look for a young woman who can rock those shorter shorts.

If that’s not you, opt for longer ones. The point of this outfit is the suede fabric, the tan color, and the styling over the white shirt.

It’s very Italian, very chic, and perfect for Fall.

Feminine Meets Modern

Speaking of Fall, this is how I would style shorts when I am ready to bring in that burgundy we all love. However, if you’ve read my Spring Summer Trends Report, you know that this is an outfit you could have worn in Spring and Summer too!

How to copy that chic look:

1. Focus on the A line style of the shorts
2. Wear your shirt partly untucked for that effortless vibe that also feels quiet modern.
3. Those slingbacks make the outfit – adding femininity and elegance with one piece.
4. That vintage Bottega style pouch purse is all I am dreaming of right now. What about you? Do you love it too?

More Italian Style Guides To Inspire You

If you enjoyed these outfit ideas, please give this post a heart and share it with a friend.

Read these next:

Cap Outfits: Milan’s Coolest Looks (more shorts inside)

How To Style A White Shirt Like An Italian Woman

Effortlessly Chic White Jeans Outfits From Milan

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Thanks for reading.

A presto,
Alessia.