Travel Outfits for Women Over 50: Inspired by Italian Style

Are you about to start packing for your Spring or Summer vacation, and not quite sure what to wear?

Hi friend, and welcome.

I’m Alessia, the writer and founder behind Italy with an Italian.

In today’s post, I’m sharing stylish and practical travel outfits for women over 50. They’re great for days when you want to look put together, feel comfortable, and maintain that classy style you love.

These are the kind of outfits Italian women wear when they want something more relaxed, but still want to look elegant and well-dressed.

Let’s see them together.

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.

A Few Tips Before You Start Packing

Before I show you the travel outfit ideas, I’d like to share a few tips to help you find that balance between comfort and elegance.

They’re inspired by the same outfits you’re about to see, so they’ll also help you understand how to recreate them.

You might even find they answer a few of the questions you already have in mind.

1. Prioritize what’s comfortable to you

If comfort is a priority for these outfits you are about to put together and pack in your suitcase, you need to lead with comfortable clothing.

But what’s comfortable to me might not be the same for you.

So ask yourself the question – what do I feel most comfortable wearing?

For some women, it might be dresses. For me, it’s trousers. For others might be jeans.

Do the same for different clothing categories – bottoms, tops, outerwear, shoes, even accessories.

What type of bag is the most comfortable when you travel? Is it it a small cross body bag, or do you prefer a large tote. It’s also ok if you like something more structured and elegant.

This is my favorite travel bag. It’s minimalist, stylish, lightweight, very spacious, and comes in different colors.

If you are worried that by prioritising comfort you’ll end up looking frumpy, carefully observe the outfits I am about to share. They are inspired by real outfits worn by women over 50 in Milan. They are chic and also look comfortable. Try to find a similar balance.

2. Shoes are a very important piece of your travel outfit.

It’s nearly always the shoes that make us the most uncomfortable, when they are not right. Can you relate?

Here are a few tips to avoid that:

1. Never, and I say never, wear a new pair of shoes on vacation, or on a long day when there’s lots of walking involved. Always test them out in advance, wearing them for only a couple hours at first. I am sure I don’t have to tell you this. After all, if you are reading this, chances are that you are mature and more experienced than me. But sometimes we all need to be reminded about things we already know.
   
2. Again, consider the type of shoes your feet feel the happiest wearing. If your feet are sensitive like mine, it might be a pair of soft shoes with a little support and that involve wearing socks. I know what you are thinking. Those don’t look that stylish, and I totally agree. However, there’s a way to make that work. You’ll see plenty of outfit ideas featuring sneakers in this post.

Sneakers (or trainers) are not the only type of comfortable shoe you can wear. Loafers are another great option, that offers a little more style. While they often come relatively flat, if you are flat footed or prefer having more support, that are brands like Tods, Geox, and Scarosso, that offer more ergonomic options.

Flat sandals with a low platform and a soft cushioned sole can be another one. However, make sure that nothing is rubbing against your skin. The super comfortable and ergonomic sandals I wore on vacation last Summer completely blistered my feet.

You might need to wear plasters or use a fabric wrap around those areas. If you have sensitive feet, it’s best to do so before you get the blisters. Or simply limit yourself to wearing the sandals for dinner, while you do most of your walking in something a little more protective.

3. Make sure each outfit includes at least one tailored piece.

This is the real secret to achieving that comfort-elegance balance we are all after, at least on vacation. You can read more about this here: Tailored Style Explained: The Italian Way to Dress Chic.

Reading that post, before or after looking at the outfits I am about to share will help you understand why those outfits look so put together, while also having that element of comfort.

You too can achieve that.

Just keep in mind this: when you are wearing a more relaxed piece of clothing, like a pair of jeans, or sneakers, the rest of the outfit needs to work a little harder to help you look chic. Adding a tailored piece, or a serious of tailored pieces, is the best way to look put together, even when you are wearing sneakers.

If you would like tips on how to pack smartly, and make your travel wardrobe pieces work harder for you, I suggest reading this guide: Packing List & System: Goodbye Stress & Overpacking. It comes with a handy packing checklist for each season.

Practical & Stylish Travel Outfits For Women Over 50

It’s time to look at those travel outfits for women over 50 I have been hinting to. Let me remind you that this posts focuses on lighter outfits. You can find Winter outfit ideas in this other post: Stylish Italian Winter Outfits For Women Over 50.

Let’s start with an outfit that clearly shows the effect of tailoring when paired with more casual pieces – like that simple black tshirt and the more relaxed shoes. I want to give you three styling options, for different levels of put together and different body types. That way, you can see that this outfit could work whether you are a size 10 or a size 16. If white trousers are outside your comfort zone, just swap the colors.

Next is another great example of something we’ve talked about. You can look put together when wearing trainers, you just have to use tailored pieces smartly to offset the casual effect that sneakers create. Can you see how that outfit does that? If you can’t read my tailored style post, and you’ll get it.

Honestly, I never thought that layering two shirts could look this good, until I saw a woman over 50 wearing this outfit in Milan.

The third travel outfit for women over 50 is the most casual one, at least in my opinion, and that’s because I’d say this dress is the least tailored piece of all the clothing pieces we are going to see here. On top of that, it’s being paired with a pair of sneakers. It doesn’t matter, though. If you like it, go for it. But if you want to elevate it further, a darker color dress, with a more structured fabric might do the trick. Or you could can dress it up with low heeled sandals.

If you’re after that very Italian timeless effortless simplistic style, here’s an outfit you’re going to love. I am going to show you how it can work for different ages over 50, and different body shapes too.

I’ve mentioned this guide focuses on the coming seasons in the Northern hemisphere – Spring and Summer, so most of the outfits are sleeveless or short sleeved. However, you might be traveling to somewhere fresher – like Scandinavia, or perhaps going on vacation during the breezy Spring months. If that’s you, here are a few outfits that incorporate multiple layers.

There’s one for the ladies who feel comfortable in skirts, one for the ladies who like an elevated casual look, and one for the ladies who prefer more elegant outfits. Which one feels more like you? It’s ok if you like them all. That’s the beauty of clothing.

Are you going somewhere warm but very chic, maybe Positano or Capri, Taormina, or Portofino? Here’s an outfit that’s perfect for that type of vacation. This could also work if you are going to Nantucket, or Fort Lauderdale.

Whether you are coming to Italy, or going to France, if you love that effortless tailored look that also blends comfort and ease into an outfit, here’s one to recreate. It’s a casual tailored look with sneakers that feels very classy. Would you wear it? It’s ok if you want to recreate it in black, or khaki!

You might be asking yourself, where are the jeans? Alessia, we are going on vacation.. Can’t we wear jeans? Of course you can! If you want more jeans outfit ideas that look stylish just like an Italian woman would wear them, here’s an entire post about them.

15 Blue Jeans Outfits From Milan – Effortless & Chic

And here’s one outfit idea with jeans for your travels. I am showing you how to style it, whether you are a size 10 or 16.

If you prefer more casual outfits, perhaps you are going for a relaxed weekend by the sea or the lake, but still want to look and feel fabulous, here are two outfit ideas.

The second could definitely work in a city, while the first one might work depending on how casual that city feels. For example, it might work in Taormina or Copenhagen, but not so much in Milan, unless it’s the hottest time of the year.

For the ladies that feel most comfortable in skirt and dresses, here are two outfits that are feminine, classy, but you can dress them up or down with your accessories. You can also swap the blazer for an over the shoulder jumper, or a cardigan. That’s going to dress the outfit down, because it’s going down the tailored spectrum.

Throughout this post, I focused on sharing mostly outfits you would wear in the morning and feel comfortable wearing to dinner. Here are another two examples. These outfits can be worn all day long, and then when the evening comes, you can chose to swap your shoes and bag, add more jewellery, and you are good to go. However, you don’t have to do that. The flat sandals work just fine.

More Outfit Ideas If You Are Over 50

Today, you came looking for travel outfits. I hope you found the inspiration to help you plan and pack for your trip.

Next time, it might be a wedding, work outfits, or your day to day life. If so, I have plenty of other outfit guides for women over 50. They all have one thing in common – they aim to make you feel your best, no matter your age.

Here is a list of those guides. You can bookmark this page and come back later, or you can take a peek now, because you might find a travel outfit idea in one of those other guides.

22 Classy Italian Outfits For Women Over 50

Stylish Feel-Good Italian Winter Outfits For Women Over 50

Airport Outfits An Italian Woman Would Actually Wear

Summer Outfits For Women Over 50 (Spotted In Milan)

Don’t stop at those guides! All my fashion posts are ageless because they focus on sharing tasteful and elegant outfit ideas, the kind of outfits that are ageless, and that you can easily tweak to make them your own.

Before you go, I’d like to invite you to join my newsletter – Buona Settimana. It’s like chatting with an Italian friend about fashion, recipes, Italian life and travel. You can subscribe through one of the sign up boxes on this page. If you do, you’ll receive my email every Sunday. I’d love to connect with you.

Thank you for reading. Please share this with a friend, or two.

A presto,
Alessia