What Not to Wear in Italy (and What to Wear Instead)

You want to be comfortable when you’re exploring Rome or strolling through Tuscany — of course you do. But does comfort mean sacrificing style? Not if you do it the Italian way.

When you look around the streets of Rome, Florence, or Venice, it’s often easy to spot the tourists. Cycling shorts, leggings with long t-shirts, baggy mid-thigh shorts, clumpy sneakers, and floppy cotton hats — these are the tell-tale signs of “tourist wear.” While practical, they’re rarely flattering, and often less comfortable than you might imagine. Synthetic fabrics cling in the heat, trainers feel heavy after hours of walking, and ill-cut shorts do no favours for anyone.

The good news? There are so many alternatives that are stylish, breathable, and effortless. Natural fabrics such as linen, cotton, and silk keep you cool. Flowing midi dresses, tailored shorts, chic sandals, and lightweight shirts not only look elegant but also feel far more comfortable in the Italian sun.

I’ve created some visuals to show the difference: the “typical tourist look” versus chic Italian-inspired alternatives. You’ll see how a little more thought — and a touch of care — completely transforms the way you present yourself.

Because yes, you’re on holiday. And no, you may never see those people again. But caring about your style is also caring about yourself. And isn’t that what la dolce vita is all about?

What not to wear in Italy - and what to wear instead -

Lilysilk

Geox

Vivaia

Ovye

Geox

Hats from Nordstrom

Dressing beautifully for Italy doesn’t need to be complicated — it just takes a little thought, a few well-chosen pieces, and the right guidance. My Travel Capsule is designed to make packing simple yet stylish, so you always feel at ease and elegant on your trip.

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Or, if you’re ready to immerse yourself fully, my Italian Style Retreats invite you to experience elegance, culture, and la dolce vita in person.

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Italian Style Tips For Women Over 50: The One Piece Every Italian Woman Has in Her Wardrobe — and Why You Should Too

There’s something unmistakably elegant about Italian women. It’s not just the clothes — it’s the attitude. The way they move through the world with quiet confidence, unhurried grace, and a sense of self that isn’t swayed by trends.

And while their wardrobes may vary — from Milan’s sleek minimalism to the romantic ease of the Amalfi coast — there’s one item you’ll almost always find hanging in their closets:

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A well-cut jacket.

Whether it’s a softly structured blazer, a cropped boucle number, or a lightweight linen jacket for warmer months, the right jacket instantly elevates an outfit. And for the Italian woman, it’s more than just a layering piece — it’s a signature.

Why the Jacket Is an Italian Wardrobe Essential Italian Style Tips For Women Over 50

Italian style isn’t about chasing trends. It’s about intention — choosing pieces that make you feel confident, comfortable, and unmistakably you.

A well-fitted blazer or jacket does several things at once:

• Pulls an outfit together – even if it’s just a tee and jeans underneath.

• Adds structure – creating flattering lines, especially around the shoulders and waist.

• Conveys effort – without being fussy or overdone.

The jacket says, I care how I show up, even if I’m just popping out for a coffee.

Italian Style Tips: How to Wear a Jacket Over 50

Here are three ways to style a jacket with that effortless Italian flair, no matter your age or body type. Italian Style Tips For Women Over 50

1. With a White Shirt and Classic Denim

A timeless Italian outfit formula seen from Turin to Palermo. Keep the denim classic (no distressing), the shirt crisp or softly rumpled, and add a statement earring or a chic flat slingback.

2. Over a Midi Dress

Pair a fluid dress in a soft floral or neutral tone with a slightly boxy jacket for contrast. Roll the sleeves, carry a structured bag, and add your favourite fragrance.

3. With Tailored Trousers and a Simple Tank

This is modern Italian power dressing. Add a low block heel or loafer, oversized sunglasses, and a silk scarf tied to your bag or wrist for extra flair.

Why This Works So Well for Women Over 50

Many women over 50 tell me they feel “invisible” — unsure what suits them now, or worried about “doing too much.” The Italian jacket is the antidote. It brings polish, presence, and personality. It’s a piece that holds space for you — without shouting.

When you find one that fits perfectly, it becomes your most-worn item — a quiet statement of beauty, elegance, and visibility.

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Find Your Perfect Italian-Style Jacket

Choosing the right jacket is all about proportion, fit, and fabric — and when you get those details right, it can transform how you feel in your clothes.

This is exactly the kind of piece we focus on in my 1:1 session, The Dolce Vita Travel Capsule Together, we define your personal style, curate your wardrobe, and infuse it with Italian confidence and elegance.

Explore the session here →

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What Tourists Get Wrong About Italian Style (and How to Dress Like You Belong) - What to wear in Italy

This morning, I sat in the piazza with my usual caffè, watching the daily wave of tourists spill into Tarquinia — sun hats bobbing, backpacks swinging, and cameras ready. My husband and I have a bit of a game we play: guessing where people are from based purely on their outfits. And trust me, we’re rarely wrong.

It’s not about mocking — it’s actually fascinating. Clothing really does tell a story. And in Italy, it tells you everything.

So what gives them away?

Let me paint you a picture.

• The oversized cargo shorts and slogan t-shirts? Probably American.

• The bright technical gear and hiking sandals? Likely German.

• The head-to-toe black with designer logos? Parisian, possibly.

• And the Italians? They're barely distinguishable from the locals... because they are the locals.

The thing is, Italians don’t just dress up — they dress with intention. Even for a trip to the market or a quick coffee.

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Here’s What Most Tourists Get Wrong About Italian Style:

1. Dressing for comfort over elegance.Of course you want to be comfortable while traveling — but Italians manage to do both. Linen trousers, a light cotton shirt, leather sandals: chic and breathable.

2. Choosing function over form.Bulky backpacks, hiking gear in the middle of town, or outfits that scream “practical” over “presentable” stand out instantly. Italians are masters of blending the two — a roomy tote, a wide-brimmed hat, stylish sunglasses.

3. Not thinking about the silhouette.Italian style is all about balance — slim cropped trousers with a flowy top, or a fitted dress with simple flat sandals. The clothes skim the body and move beautifully.

4. Sticking to fast fashion or logo-heavy looks.Italians favour quality basics that last. Think neutral tones, natural fabrics, timeless cuts. You won’t find many logos or TikTok trends here.

5. Forgetting the power of grooming. Hair brushed. Lipstick on. Sunglasses polished. Even the most casual outfit is elevated by attention to the little things.

How to Dress Like You Belong in Italy (Even Just for the Day)

What to wear in Italy. Here’s what I recommend if you want to blend in — or at least not feel like a walking tour group:

• Pack fewer pieces, but choose better fabrics and fits.

• Neutral colours + one pop (a scarf, a bold earring, a red lip).

• Leave the athletic wear for the gym — opt for linen, cotton, and breathable pieces.

• Choose chic leather sandals or loafers over chunky trainers.

• Add a pair of sunglasses, a crossbody bag, and a relaxed air of nonchalance.

Want Help With What To Wear In Italy and Creating an Italian-Inspired Wardrobe?

This is exactly what I help women do — whether you're visiting Italy, living here, or just longing to bring a little la dolce vita to your wardrobe.

You can start with my free guide: “Pack Like an Italian” — it’s filled with tips to create a travel wardrobe you’ll love to wear (and be photographed in).

Or if you're ready to go deeper, my Taste of La Dolce Vita session is a personal, joyful way to reconnect with your essence and your style — Italian style.

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