Cap Outfits: Milan’s Coolest Looks (For Him & Her)

Baseball cap outfits aren’t something you usually associate with Italian style, right? And you’re not wrong.

Until a few years ago, you’d rarely see an Italian woman in a cap unless she was hiking or cheering at a soccer game — maybe her son’s. The same was true for men, unless they were wearing one for work.

Well, things have changed.

More cool Italian girls and guys are wearing caps as part of their everyday outfits. And I must say many of those outfits look stunning.

So today, I thought I’d share a mix of cap outfits for men and women inspired by Milan street style. This way, next time you want to wear a cap, you’ll know exactly how to style it.

Let’s get started.

PS: In case you’re curious, I wear caps too every now and then. I even shared one recently in my newsletter, Buona Settimana. If you join, you’ll get access to the archive and the new emails as they come. You can sign up through any of the boxes in this post — I’d love to have you there.

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27 Stylish Cap Outfits From Milan

In this collection, I tried to curate outfits that work for different ages, as well as showcase how both Italian men and women wear this accessory throughout the seasons. We are starting off with Summer and transitional outfits. We’ll then move onto more Wintery looks.

Cap Outfit Ideas For Any Age & Style

Of course, I’m starting with one of the coolest looks: an oversized yet tailored outfit that looks stunning with a cap. If you’ve ever wondered how to pair tailoring with a cap, this is a perfect example — modern, effortless, and a little edgy.

I have seen a lot of questions around wearing dresses and caps, and I get why. Many women like to wear dresses on vacation but they also like the cap for sun protection. This outfit is a great example on how to wear a dress with a cap to look good while also being comfortable.

Want more ideas on how to style a cap with a tailored look? Here’s another one. This is definitely not the kind of outfit you would wear to a corporate job, but if you work a more relaxed job, or even better you are self employed, you make the rules. Creative jobs call for creative outfits!

Going to grab a coffee with a friend but didn’t have time to wash your hair? Wear a jeans and a cap kind of outfit, but make sure those jeans fit you like a glove and don’t look slouchy, plus add a structured bag to make things look dressier than they are.

Caps Over 50?

Calling my lovely readers over 50. If you think you can’t wear a baseball cap after a certain age, you are wrong.

Of course, not all hairstyles will suit one, but look at this stunning lady and how she is wearing a comfortable and fairly casual outfit that still looks put together. She could be on vacation or running errands.. Either way, she looks fabulous. That beautiful white shirt maxi dress definitely elevates this cap outfit.

Summer Cap Outfits For Women

I have seen plenty of searches around how to wear a cap in Summer for women. You can wear it with shorts, both shorter or longer bermuda-style. Let me share four different outfits.

They all happen to be white shorts because Italians love wearing white bottoms in Summer. However, each has a different vibe.

The first feels dressy but fun. It could be worn in the morning on vacation or shopping; you could remove the cap to go to for dinner.

The second feels classic and cool at the same time, is the most comfortable because of the flat shoes, and it’s a great one to wear on vacation.

The third one is the perfect Summer to Fall transitioning outfit if you fell like you still can’t put those shorts away.

The fourth one is a little more chic and tailored, and the linen fabric makes it a great hot Summer kind of outfit.

Speaking of white bottoms, wondering how to wear a cap with white trousers? Here’s an idea.

When it’s really hot – think August in Rome, you can pair your white pants with a dressier tank top, a nice bag and a colourful shoe. The cap dresses things down in this case but also gives it an edgier vibe.

A white skirt and top set is a must have if you love wearing this color in Summer. That blue cap adds that little bit of color this outfit needs and it also makes it a little more playful. Do you agree?

Here’s another dress and cap outfit idea, but this time we are playing with pink tones. How stunning is that mustard toned tan cap paired against the pink dress?

Classic Cap Outfit Ideas for Men

Let’s now look at how men can wear caps in true Italian style.

We are starting with one of the most classic looks ever – a pair of beige chinos with a light blue polo shirt and a pair of lace up shoes worn with no socks.

Can you see how that red cap gives the outfit that pop of color that takes it from being just anyone’s outfit to being yours, if that’s your style. That small detail makes it unique!

The same holds for this next look. This is a very popular kind of outfit among older gentlemen, but this man has given the look his personality by just adding that beige cap.

Next, is a very cool Milanese guy kind of look – wide leg trousers with a tshirt tucked in, a pair of cool chunky trainers, and a baseball cap that ties in with the outfit color palette. It’s cool but it still looks classic because of the tailoring and the colors.

Winter Cap Outfits For Men & Women

Winter Cap Outfits For Men

In case you are wondering, more Italians wear caps during Winter than in Summer. That’s because caps serve as a winter accessory, especially for men.

If you too want to wear more baseball cap outfits in the colder months, here are four looks to inspire you.

The first one is a very popular one among younger men. It’s comfortable, cosy, casual but still put together. The cap gives it the added personality this outfit is lacking because of how simple it is.

The second one is the kind of cool Milan man outfit you’ll see in January and February, when the weather is really cold, and fur coats are popular among men too. Adding a cap tones down the fur coat, in my opinion.

The third one is proof that the rule no white trousers after Labor day is not a thing in Italy. In reality, I did grow up hearing my parents say that you shouldn’t wear white bottoms or shoes during Fall and Winter. Maybe that’s why I don’t like wearing either. However, Italian men love wearing white trousers, and it’s evident that some of them don’t mind wearing them in Winter too.

Finally, the fourth outfit is the kind of early Winter outfit older Italian men like to wear. The cap gives it that cool factor.

Winter Cap Outfits for Women

Since we got in the Winter mood, let me show you how to style Winter coats with a baseball cap for women.

You can wear jeans or trousers for the extra warmth, chunky sweaters and scarves, you can go tonal, or add a pop of color with your hat, the bag or both.

One thing you probably can spot is that the structured tailored coat pairs really beautifully with the cool cap aesthetic.

If you want to dress up the outfit, I suggest adding a structured bag, as it contrasts beautifully against the cap.

If you want to lean more into the casual style, you can wear sneakers; otherwise, boots are a great dressier option.

If you have a fur coat and want to dress it down, try wearing it with an all black outfit and a cap. It still looks chic but with a slight edge many of us love.

Speaking of Winter, here’s another outfit idea for women over 50; but if you are younger, you can still wear it!

Wear a teddy cream coat with a matching baseball cap, and then wear a comfortable outfit underneath, pair it with heeled boots, or flat ones if you prefer, and add a pop of color with your bag.

Struggling to style your leather jacket with a cap? Here’s how Italian women do it. Of course, it can be worn with any leather jacket color. Just play with the trousers and cap colors.

Earlier, I gave you a Summer cap outfit idea for work, here’s one for Winter. This is one I am definitely recreating for the weekend. You can do the same too!

Since we are talking about cap outfits, which are inherently casual outfits, let’s end with one the most casual outfit of all.

This is the perfect running errand, teacher, busy mum Winter outfit with a cap. Yet, it doesn’t look frumpy and won’t make you cringe if you bump into that old acquaintance you haven’t met in ages.

Baseball Cap Styling FAQ

Before I sign off, I’d like to answer the most popular questions around this topic. I hope this helps you.

How to wear a baseball cap with tailoring?

The best way to pair a baseball cap with tailoring is to make sure the look feels balanced.

Here’s a tip for men. You don’t want to pair a baseball cap with a completely classic look. Instead, you can go with a more modern suit, one that has cropped pants. You can then pair it with a tailored tshirt instead of a button up shirt, and even wear loafers instead of your classic oxford shoes.

The same holds for women, when it comes to the cut and the color of the suit. However, don’t be afraid to pair a suit with heels and a cap. You can equally dress your suit down by wearing both a cap and a pair of trainers, and swapping the button up shirt with a tank top or a tshirt. This makes a great airport, vacation and casual work outfit.

How to look feminine in a baseball cap?

If your aim is to look feminine in a baseball cap while looking cool, heels are your best friend. I have shown you plenty of cap outfit ideas with heels in this post, so get inspired by them.

Your bag is another element that can help you make the outfit more feminine. If your cap outfit is feeling too cool and masculine, maybe because of the darker colors or the structured elements, consider adding a pop of color with the bag, or a bag with a softer more feminine fabric.

Pairing a cap with a dress will also give you that effect, especially if the dress is flowy. The same holds if you pair your cap with a skirt, or with a more feminine top. Again, you have at least an outfit idea for each of those.

What color baseball cap goes with everything?

What color baseball cap goes with everything depends on two things: your skin and hair color, and your seasonal wardrobe color palette. In general, however, a lighter color cap is great if you are fair or have blonde hair. The same holds with a brown cap, if you are darker or a brunette.

But if you wear a lot of black, having a great black cap is definitely a great starting point.

How to style your hair when wearing a baseball cap?

This depends on your hair length, how you usually style your hair, what suits your face best, and the outfit you are going to wear.

I personally like to wear my caps with a low bun that sits just under the cap, or with my hair down, straight or slightly wavy, but I always pull it behind my ears. But that’s what suits my face in a cap best.

You need to find what works for you, and the only way is by trying different hairstyles.