What to Wear in Italy: My Favorite 90s-Inspired Travel Outfit From Milan

Cream blazer, bermuda shorts, silk shirt, and loafers travel outfit walking in Milan, Italy

If you're heading to Italy this summer and wondering what to wear in Milan, Rome, Florence, or anywhere in between, I have a really good one for you today. This was hands down my favorite outfit from my entire trip to Italy, and based on the absolute flood of DMs and questions I got while I was sharing it on Instagram stories, it might be your favorite too.

I'll walk you through every piece, why it worked so beautifully for European travel, and how to put your own version of it together for your trip. (All of it can be found at Nordstrom: the cream blazer, the bermuda shorts, the silk shirt (or this satin alternative), the Cole Haan loafers, the silk scarf, the structured top-handle bag, and the freshwater pearl studs. Several pieces I now own in multiple colors because they're that good.)

First, some real talk on what to wear in Europe (and in Milan specifically)

Quick disclaimer before we get into the outfit: you can absolutely go to Europe and wear whatever you want. Truly. Travel is yours, your vacation is yours, and there is no fashion police waiting for you at customs in Rome. If you want to wear leggings and sneakers the whole trip, that is one hundred percent okay and you'll still have the best time.

But if you're someone who likes to respect the local culture when you travel (and I know a lot of you reading this are), here is the truth. Europeans dress smart. Italians dress really smart. And Milanese women in particular dress with this quietly polished, head-to-toe elegance that you start noticing the second you step off the plane. They care about looking presentable. They iron their shirts. They wear real shoes. They don't run errands in athleisure. There is a whole cultural value around looking pulled together when you're out in public, and once you spend a few days there, you can really feel why.

This outfit is the perfect European travel outfit because it lets you participate in that quietly. You won't show up to lunch looking wrinkly or thrown together after a long morning of walking. You won't feel underdressed when you walk past a beautiful storefront in the Galleria. You'll look like a polished professional who fits the scene, no matter where you wander.

I have to share this because it was one of my favorite moments of the whole trip. While we were shopping all throughout the Galleria and the Duomo area in this exact outfit, multiple people in multiple stores walked right up to me and started speaking Italian. I had to keep explaining (in very, very rusty English-accented apologies) that I'm actually from the United States and don't speak Italian. Every single time, it felt like the biggest compliment, knowing they would even glance at me and assume I might be a local, that I belonged in that scene. That doesn't happen by accident. That happens because the outfit fit the city, and the city is one of the best-dressed places on earth.

If that's the kind of trip you want to have too, head down to the next section.

The travel outfit that made my whole trip

Here's the test I always run on a travel outfit. I pack a travel steamer and pray I won't need it. With this look (blazer, shorts, silk shirt, loafers, scarf, bag, pearl earrings), I didn't even pull the steamer out of my suitcase. Every piece came out of my carry-on looking like it had been pressed five minutes earlier. That alone earns it a permanent spot in my Europe rotation.

But it wasn't just wrinkle-free. It was the kind of outfit that worked for a slightly chilly Milan morning, transitioned to a long, leisurely lunch with my sister, and then held up for hours of walking and shopping in the afternoon without me ever feeling overdressed or under-dressed. When it warmed up, I slipped the blazer off and looped it over my arm. When the breeze picked up again and my afternoon was met with some unexpected thunder/lightening and rain, it went right back on.

This is exactly what I want from a summer travel outfit in Italy: structured but easy, polished but not stuffy, and forgiving of the fact that you're going to walk approximately 18,000 steps a day on cobblestone.

Why the 90s-inspired, relaxed-tailored look works so well for Italian travel

Modern retro is having a real moment right now, and for good reason. The 90s “it girl” silhouette (relaxed blazer, a clean line through the leg, a fluid shirt underneath, structured shoes) is one of those looks that reads chic without trying. It's especially smart for Italy because Italian women dress with so much intention. You feel out of place the moment you slip on athletic shorts and sneakers near any of the duomos or piazzas. Tailored, relaxed pieces let you blend in beautifully while still being comfortable enough to walk all day.

Cream and ivory tones are also a major part of why this outfit looked so dressy in person. There's something about a head-to-toe neutral palette in soft creams that photographs incredibly well in European light and reads “this person knows what she's doing” without trying.

The blazer: my new cream relaxed blazer (the one I already own in black)

Cream relaxed-fit blazer styled with bermuda shorts on a Milan street

Let's start with the star of the outfit: this cream relaxed blazer. This is a new addition to my closet this season, but I've owned the black version for several years now, and it gets pulled out of my closet constantly. The fit is exactly what you want from a 90s-inspired blazer: slightly oversized but still tailored, with shoulders that hold their shape and a length that flatters whatever you put underneath.

What makes this blazer so great for travel: it doesn't wrinkle, it layers beautifully over a silk or satin shirt, and it dresses up the simplest pieces instantly. I wore mine open over the bermuda shorts and silk shirt, which gave the whole outfit that effortless, “I just threw this on” feeling that always takes the most planning. Shop the cream version here, or grab it in black if you want a workhorse you'll wear for years.

The bermuda shorts: the dressy travel short I keep buying in new colors

Cream bermuda shorts and loafers as a 90s-inspired travel outfit in Milan

These cream bermuda shorts are my favorite dressy shorts of the season. I already own them in black (a wardrobe workhorse that I wear constantly), and the cream version felt so fresh and summery that I knew immediately they had to come to Italy with me.

The length and the soft tailoring are what set these shorts apart. They're long enough to feel chic and short enough to keep you cool when an Italian afternoon turns warm. They look intentional, not slouchy. And they pair effortlessly with literally everything: silk, satin, a fitted tank, a t-shirt, sandals, loafers, sneakers. If you're trying to pack light for Europe, these are the kind of shorts that earn their suitcase real estate twice over.

The silk shirt, and a satin alternative if you don't want to splurge

Silk blend button-up shirt worn under a cream blazer walking through Milan

Underneath the blazer, I wore this Vince silk-blend button-up. Silk is one of those quietly magical fabrics for travel because it weighs nothing, packs into a tiny square, and dresses up the most casual outfit. If you've never invested in a really good silk button-up, Italy is the perfect excuse.

That said, I know silk isn't always in the budget, and the price feels like a splurge. If you want the same look without the silk price tag, this Mango flowy satin shirt is a beautiful alternative. The satin version has the same fluid drape, the same elevated finish under a blazer, and a much friendlier price point. You honestly can't tell the difference in photos.

The shoes: well-worn loafers are my biggest packing tip for Europe

If you take only one piece of advice from this post, please let it be this one: do not break in new shoes in Europe. I've made this mistake. You will be miserable. You will limp.

I wore a pair of loafers I bought a few years ago at the Nordstrom Anniversary Sale, and they were so broken in by the time I got to Milan that I walked all day long with zero blisters. If you want this exact look, the most current version of those same loafers is the Cole Haan Danby travel loafer. Same color, same silhouette. Buy them now, wear them around your house, around the grocery store, around the neighborhood for a few weeks before your trip, and they'll be ready when you need them.

Loafers are the unsung hero of European travel because they look more polished than sneakers, more substantial than sandals, and they actually let you walk for hours. The Cole Haan Danby goes with shorts, dresses, jeans, trousers, and basically everything. They're the kind of shoe you'll wear forever.

The accessories: a silk scarf, a top-handle bag, and a pair of pearl studs

European travel is the right time to lean into accessories. They take up almost no suitcase space, they elevate every outfit you packed, and they look great in photos.

Silk scarf tied in a knot at the neck with a cream blazer in a Milan boutique

I was trying on a beautiful patterned silk scarf at one of the iconic stores in Milan, and I've linked a gorgeous similar silk scarf from Nordstrom so you can recreate the look. Tied at the neck like this, the scarf gives the whole outfit a polished, intentional finish.

Silk scarf draped over a cream blazer like a stole for a 90s-inspired Milan outfit

Or wear the same scarf draped over the blazer like a stole for a completely different look from the exact same piece. Tie it on your bag handle, knot it around your neck, drape it over your shoulders, or use it as a hair scarf. One silk scarf, so many outfits.

For the bag, I picked up a small structured top-handle while I was traveling. This Tory Burch Romy slim top-handle is the closest match I've found at Nordstrom, and it's stunning. The structured shape is what gives any travel outfit that pulled-together, “I planned this” feeling. Get yours here.

And I cannot leave out the earrings. I wore these freshwater button pearl studs every single day of the trip. Pearl studs are the most underrated travel jewelry on the planet: they go with every outfit, they look effortless and elegant, they don't catch on scarves, and they look just as good with a t-shirt as they do with a cream blazer in Milan. If you don't already own a pair, these are the perfect starter.

A morning in Milan: lunch and shopping at the Galleria

Smiling at a beautiful Milan restaurant in cream blazer travel outfit

This outfit had its grand debut on what ended up being one of my favorite days of the entire trip. My sister and I had lunch at this gorgeous restaurant tucked inside one of Milan's most iconic stores, the kind of place where every detail has been considered and the food is as beautiful as the room. Wearing the blazer, shorts, and pearls there felt exactly right.

Selfie with my sister on a sunny Milan street during our trip to Italy

If you've followed me for any amount of time, you know that traveling with my sister is one of the great joys of my life. She makes every meal more fun, every wrong turn into a memory, and every museum more interesting. This day in Milan was one for the books.

Lunch in Milan at a beautiful restaurant in cream travel outfit

After lunch, we walked through the Galleria Vittorio Emanuele II, which is one of the most famous shopping destinations in the world and absolutely the heart of the fashion capital. I tried on a beautiful silk scarf at one of the legendary boutiques (linked above to a very similar one you can shop from Nordstrom!), wandered through the marble arcades, and looked at every window display in awe. If you've never been to the Galleria, put it at the very top of your Italy list.

This is exactly the kind of day I dressed for: elegant lunch, hours of walking on marble and cobblestone, mixing the casual energy of shopping with the elevated feel of being in one of the world's most beautiful cities. The blazer, shorts, silk shirt, broken-in loafers, and pearl studs did all of it without a single wardrobe regret.

My biggest packing lesson from this trip to Italy

If I had to distill everything I learned about what to wear in Italy into one sentence, it would be this: pack pieces that work harder than they have to. A blazer that goes from morning chill to evening dinner. Shorts that look as dressed-up as trousers. Shoes you can walk 20,000 steps in that don't look like walking shoes. A silk shirt (or a satin alternative) that doesn't wrinkle. A scarf that becomes three different accessories. A bag that goes from lunch to long walks without missing a beat. A pair of pearl studs that finish every single outfit.

That's what made this outfit my favorite. Every single piece earned its place in my carry-on twice over, and now they're all earning permanent spots in my closet at home, too.

FAQ: What to Wear in Italy

What should I wear in Italy in the summer?
For Italy in the summer, focus on lightweight, breathable fabrics like silk, linen, and cotton in a neutral palette (cream, ivory, beige, black, navy). Italian style leans elevated and tailored, so swap athletic wear and sneakers for relaxed blazers, dressy shorts or trousers, fluid blouses, and broken-in loafers or stylish flats. A silk scarf, a small structured bag, and a pair of pearl studs are easy ways to look polished without overpacking.

Are loafers good for walking in Europe?
Yes, loafers are one of the best shoes for walking in Europe, as long as they're already broken in before your trip. They look more polished than sneakers and more substantial than sandals, and a quality pair (like the Cole Haan Danby travel loafer) can handle hours of cobblestone walking without giving you blisters.

What is the dress code in Milan?
Milan is the fashion capital of the world, so locals tend to dress with intention. There's no formal dress code for restaurants and shopping districts, but you'll feel out of place in workout clothes or beach attire. Aim for tailored, elevated basics like relaxed blazers, dressy shorts or trousers, button-up shirts, and structured shoes. Tonal neutral outfits read especially well in Milan.

What is a 90s-inspired outfit?
A 90s-inspired outfit borrows from the relaxed, tailored, “it girl” silhouettes of the era like oversized blazers, slip dresses, fluid silk shirts, bermuda shorts, slim trousers, and structured loafers. The modern retro version pairs those vintage shapes with current fits and updated styling for a look that feels both nostalgic and fresh.

How do I pack a wrinkle-free travel outfit?
Choose fabrics that resist wrinkles like silk, satin, lightweight wool blends, and many modern blazer materials that hold up beautifully in a carry-on. Roll (don't fold) softer pieces, and pack a small travel steamer just in case. The cream blazer, bermuda shorts, and silk shirt outfit linked in this post all came out of my suitcase ready to wear with no steaming required.

What jewelry should I pack for Italy?
Keep it simple, classic, and small. A pair of pearl studs like the freshwater button studs I wore all over Milan will go with every outfit you packed and never look out of place at a nice dinner or a quick coffee. Skip the statement pieces you'd worry about losing.

Where should I shop when I'm in Milan?
The Galleria Vittorio Emanuele II is the most iconic shopping destination in Milan and absolutely worth a visit, even if you're just window shopping. Via Montenapoleone is another famous fashion street. For souvenirs and beautiful accessories like silk scarves and leather goods, the boutiques inside the Galleria are unforgettable, even if you save the actual shopping for back home.