These 20+ Italy Outfits Will Have You Dreaming of an Italian Summer Getaway

Italy Outfits

Did you see that Erin and her family just took a trip to Italy? We shared their full Italy itinerary in this post if you missed it. They went as an early birthday celebration for Erin’s 50th and Erin was SO excited to roam the streets of Rome and relax in Positano and Capri. Another thing she was excited about? Wearing some incredible outfits while she was in these gorgeous destinations. Below we’re sharing all of the stunning Italy outfits Erin packed for her trip…

If you’re looking for even more travel inspo, check out this page next!

Italy travel

Italy Packing

Before we dive in, we want to touch on Erin’s packing. We’re sharing a post tomorrow about what to pack for Italy regardless of your bag size. Today’s post is definitely a maximalist approach. Erin packed extra for this trip because she knew she wanted to shoot photos while she was there and even met up with a magazine photographer in Rome. She packed all of her outfits into a giant checked suitcase and a carry-on suitcase (with valuables, toiletries and enough clothes just in case). This is NOT packing light and we know that! 😉 But these looks should give you some great ideas for tailored Italy outfits that are chic, sophisticated, and glamorous. First, you’ll see day-to-day outfits, but keep scrolling to see the really special, stunning, standout pieces too…

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Italy travel outfits

Outfit #1) Travel Outfit

First up is Erin’s travel outfit. She went with a pair of comfortable baggy jeans because she didn’t want to wear sweatpants all day, but packed a pair of sweatpants in her carry-on and changed into them for the overnight flight for comfort. She has on an ivory Balmain blazer that’s super sophisticated and polished and really brings the look together. Underneath that, she’s wearing a sleeveless open-knit sweater that’s lightweight and breathable. Underneath the open-knit sweater, she has on a ribbed tank and a bralette. The entire look is very cozy and layering this way saves space in a suitcase if you need it. On her feet, she has on a pair of super comfortable white Linea Paolo sneakers that have summery jute details. You can’t see them in the photo but you’ll see more of them in the following looks…

Want to know more about building the perfect travel outfit? Check out this post next!

Cinq a Sept tweed dress

Cinq a Sept tweed dress Italy Outfits

Cinq a Sept tweed dress Italy OutfitsCinq a Sept tweed dress Italy Outfits

Outfit #2) Dinner In Rome

On their first night in Rome, Erin wore this chic, 60’s inspired, pink Cinq a Sept tweed dress. We love the elevated look of the material, contrasting white trim, and luxe gold buttons. It’s sleeveless so that’s something to keep in mind. Erin threw on a sophisticated white cropped jacket over this dress that she wore nonstop on this trip! It’s a tweed material but it’s pretty lightweight, making it perfect for the warm days and cooler nights in Italy. For dinner in Rome, she wore the same Linea Paolo sneakers (left). But for a day in Positano, she wore the dress with some white wedge sneakers by Valentino that have the brand’s classic stud details. Finally, she completed the look with a white Valentino handbag that was perfect for carrying all of the essentials on her trip (it’s the mini size). It has a cool gold V-logo top handle but you can also carry it crossbody with the shoulder strap.

Italy Outfits mini dressItaly Outfits mini dress

Outfit #3) Sightseeing Day

For a sightseeing day in Rome, Erin wore this cute, lightweight mini dress by Staud. Erin has the midi version of this dress in two other colors and loves them so much she got this gorgeous blue toile pattern in the mini length too! It was perfect for keeping cool on a day of seeing lots of attractions in Rome. She styled it with a white Valentino belt to add more waist definition, the same white handbag, and the same pair of white wedge sneakers. These sneakers are so great because you get some added height, but don’t have to worry about wearing actual heels on the cobblestone streets.

Erin also wore the dress for a night out to dinner in Positano. She added a lightweight cotton sweater in case she got cold, a chunky gold necklace to dress it up, and a pair of comfortable metallic gold flats by Pedro Garcia to make the outfit feel more evening-ready.

romper Italy outfits

travel romper outfit crossbody bag for travel

Outfit #4) Colosseum Tour

For a tour of the Colosseum, Erin knew she wanted to stay cool and comfortable so she opted for this super cute terry cloth romper that looks like a blazer dress. We love the gold button details and black and white contrast. The asymmetrical hemline is also very flattering. She wore it with a pair of super comfortable metallic flats by Cole Haan that were perfect for a lot of walking.

tailored vest and matching pantsvest and matching pants Italy Outfits

Outfit #5) Dinner & Spanish Steps

The Busbee’s enjoyed a nice dinner and headed to the Spanish Steps one night so Erin wanted to look polished for dinner, but still feel comfortable enough to do some walking afterward. She wore this gorgeous tailored vest and matching pants from Aritzia. You can wear these pieces together or separately, making them great, versatile additions to a travel wardrobe. Erin wore her white wedges sneakers and handbag and threw the white tweed jacket on at night when she got cold. But she also styled the look with a pair of slingback pumps and a hat to elevate it during her photoshoot…both looks are equally chic!

Bronx & Banco dress.

Bronx & Banco dress Italy outfits valentino white bag

Outfit #6) Vatican City Tour

Erin decided to dial up the drama for their Vatican City tour and went with this gorgeous Bronx & Banco dress. How gorgeous is this tulle and lace detailing?! When you go to religious sites, you’ll need to make sure your shoulders and most of your legs are covered. This dress has lining to the knee and the sheer tulle fabric extends almost to the ankle. She threw on the white cropped jacket when they went into the church. She completed the look with the same white handbag and the metallic flats from outfit #3. These flats are incredibly comfortable and SO good for lots of walking.

black Maygel Coronel bikini

Outfit #7) Lunch & Beach Day

Now for some swimwear looks…Erin wore this fabulous black Maygel Coronel bikini to lunch followed by a beach day. How amazing are the shoulders on this bikini top?! To cover up a bit, she wore a pair of ribbed knit pants that are super thin and lightweight. It’s hard to tell in the photo above but they are actually pretty sheer and see-through. She completed the look with a pair of Sam Edelman flats, an Ulla Johnson tote bag, and a black sunhat. This is a glam beach or pool day look if you’re headed somewhere like Positano or Capri!

Staud swimsuit

Outfit #8) Boat Day

For a boat day in Positano, Erin grabbed one of her new favorite swimsuits by Staud. She has this swimsuit in two colors and took the white version on her recent trip to Vietnam & China. The cutouts on the sides are super flattering and cheat the waist in, which is always a win with swimwear! She’s wearing the same lightweight knit pants, metallic Pedro Garcia flats, and a sunhat by Physician Endorsed. Erin recently discovered this brand and really loved this hat. It has a 4” brim and UPF 40+ sun protection!

navy and white swimsuitnavy and white swimsuit Italy outfits

Outfit #9) Pool Day

This is another gorgeous swimsuit by Staud that Erin saw and just had to try! She loves the nautical look, navy and white color combo, and luxe gold button details. The plunge neckline is sexy but not too revealing (depending on cup size) and since it’s a one-piece you get a good amount of coverage. The bottom coverage is minimal – definitely keep that in mind.

white bikini

white bikini in Italy white bikini Italy outfits

vix white bikini

Outfit #10) Pool Day

Next up is a fabulous pool day outfit. Erin’s wearing a white bikini that she’s had for years by Vix. The real showstopper, though, is this coverup! We love the bright, vibrant colors, you can wear it open or closed, and it’s a great length for full(ish) coverage. The material also has some metallic threads that really make it shine (literally and figuratively). Throw this coverup over your white swimwear to instantly elevate it and feel more fabulous.

bikini set by OYE Swimwear
bikini set by OYE Swimwear

Outfit #11) Beach Club Day

This swimsuit is a wildcard but it’s so chic and cool we had to share! This bikini set by OYE Swimwear has sexy gold buckle details that make it a really cool swimsuit. Erin admitted it was a little difficult to get into, but it’s super chic and a real standout piece if you’re headed to a beach or pool club in Positano, Capri, or even somewhere like Vegas or Miami.

blue printed dress Italy Outfits

blue printed dress Italy Outfitsvalentino belt

Outfit #12) Exploring Positano

Now that we’ve covered all of the swimwear looks Erin packed, let’s dive into some of the beautiful dresses she wore while in Italy. First up is this blue-printed beauty by Avara…we still can’t believe this dress is under $100! Erin dressed it up for dinner with the Pedro Garcia flats, a chunky gold necklace, a white cropped jacket, and a white belt and handbag. She also styled it with wedge sneakers, showing that you can really change up the look of this dress based on the accessories you style it with!


Dinner in Capri

Dinner outfit in CapriDinner dress Italy Outfits

Outfit #13) Dinner in Capri

For a night out to dinner in Capri, Erin wore this Bronx & Banco set that walks the line between sexy and feminine. The top and skirt both have delicate floral lace details and we love the straps on the top. This set does show some midsection so if that makes you uncomfortable, opt for the white Bronx & Banco dress Erin wore in outfit #6 instead. You’ll get a similar look without showing so much skin. For dinner, Erin completed the look with wedge sneakers, the white cropped jacket, a chunky necklace, and her white handbag. You could dress it up even more by wearing it with heels or platforms instead, but Erin knew she’d be walking a bit so she went with the sneakers.

Quince silky skirt

Quince silky skirt white top Quince silky skirt white top Italy Outfits

Outfit #14) Shopping Day

This look would be perfect for a shopping, exploring, or sightseeing day. Erin’s wearing a silky skirt by Quince that’s washable. Amazing, right?! The fit is great, it comes in multiple colors, and Erin loves the longer length. She styled it with a simple white ribbed tank to make it more casual and tied a lightweight sweater around her shoulder. She completed the look with simple jewelry, her Valentino handbag, and the Cole Haan ballet flats.

matching red Farm Rio shorts set

matching red Farm Rio shorts set Italy Outfits

matching red Farm Rio shorts set Italy Outfits red top and gold necklace

Outfit #15) Dinner Outfit

If you’re an IG follower, this outfit probably looks familiar. Erin loves this matching red Farm Rio shorts set…the color, the fit, the fabric, and the versatility all make this such a good set to take on a trip or even just to add to your summer wardrobe. She styled the set with some platform heels and a trendy raffia clutch but you could dress this up or down with different shoes and accessories.

black off-the-shoulder top Italy Outfits

black off-the-shoulder top Italy OutfitsPrada bag

Outfit #16) Night Out Outfit

This look would be perfect for a night out or dinner whether you’re on vacation or not. Erin’s wearing a stunning black off-the-shoulder top by Cult Gaia that’s super flattering and chic. She styled this top with a pair of jeans for a casual date night in this post. But to dress it up more, she styled it with a pair of contrasting white and black wide-leg pants by Reiss. These pants have a drawstring waist but are very elevated and super flattering. They have a seam down the front that also elongates the legs. She completed the look with a pair of slingback pumps and a classic black Prada handbag. Note: If you’re walking to dinner, you would want to swap the heels for something more practical like wedges or a block-heeled sandal.

Elevated Brunch Outfit white vest and pants

Outfit #17) Elevated Brunch Outfit

This set may look familiar and that’s because it’s the same tailored vest and pants from outfit #5, but in white! This color feels more daytime chic versus the black. This set has the same amazing fit, elevated feel, and maximum versatility for a trip. Erin styled it with white sneakers and a chic hat, making it perfect for brunch or a day of shopping and exploring.

blue-printed mini by Aje blue-printed mini dress

Outfit #18) Day to Night Dress

Looking for the perfect day-to-night dress?? This blue-printed mini by Aje is SO good! We love the bright, bold blue that looks good on so many skin tones, the fit is very flattering, and the length is nice. Wear it alone with sneakers during the day and dress it up with a belt, chunky jewelry, and heels for dinner like Erin did. BTW, Aje has several pieces with this exact print that you can check out.

halter neck mini dress Italy Outfits

Staud mini dress

Outfit #19) Exploring Day

Next up is a chic mini dress by Staud. We love the halter neckline and dramatic bow at the back. The navy and white has a very nautical feel, making it perfect for a sunny vacation getaway. This is one of those dresses that can serve so many purposes…it’s just that versatile! Style it with sneakers for a day of exploring or heels for dinner.

green Farm Rio dress in Italy

Outfit #20) Sunset Dinner or Beach Wedding

This green Farm Rio dress is so chic, breathable, and versatile. Erin has worn it with heels, sneakers, and sandals this summer and loves how easy it is to dress up or down! The one-shoulder neckline is really cool, the print and color are beautiful, and the length is nice too. You could wear this to dinner, lunch, sightseeing, or even to a beach wedding this summer!

white L’IDEE gown

white L’IDEE pleated gown

L’IDEE pleated gown open back

Outfit #21) Dressy Event

This white L’IDEE gown is a serious showstopper. Everything from the long, flowy length to the beautifully pleated fabric to the sexy open back and plunge neckline…it’s perfection! You could wear this to a gala, event, or just on vacation if you’re looking for a piece that will truly make you feel fabulous! Erin styled it with some platforms and kept the rest of the accessories minimal to let the dress stand on its own.

Founded in 2019, L’IDEE is a new brand. This is the first piece by the line that Erin has purchased… and she is in love with it! While she was in Positano, she actually discovered a L’IDEE shop. Turns out the co-founder lives there!

Dolce & Gabbana polka dot dress Italy Outfits

Dolce & Gabbana polka dot dress Italy Outfits

Outfit #22) Dressy Dinner

This Dolce & Gabbana polka dot dress is another really special piece. Erin ordered it specifically for this trip and loves how it makes her feel. It’s sexy but playful, feminine, trendy, and just absolutely stunning. We know this won’t necessarily be a piece you’ll add to your wardrobe, but it gives you inspiration to find something you truly love for your next vacation. Sometimes just having that one special piece picked out makes you even more excited for an upcoming trip!

printed dress in Italy

Outfit #23) Elevated Dinner

This dress is probably familiar if you’re a newsletter subscriber or follow us on Instagram. Erin bought this dress earlier this year and has taken it on multiple trips and styled it multiple ways. In this look, she’s wearing it with a pair of platform heels, which would be a perfect, elevated dinner outfit. But you can style this dress with sneakers, flats, or wedges. We love the bright, bold print, flattering fit-and-flare silhouette, and sexy (but modest) square neckline.

Cult Gaia dress

Outfit #24) Cocktail Event

How fabulous is this Cult Gaia dress?! We know it’s not going to be everyone’s cup of tea, but if you’re looking to add some drama to your wardrobe or just want a special piece for your next trip, this is a fabulous option! We LOVE the oversized sleeves, interesting fabric, and drawstring details. If you’re headed to a cocktail wedding, grab the green version of this dress! BTW, this dress is SO lightweight, it’ll take NO room in your suitcase.

Staud blue toile dress Italy Outfits midi dress

Outfit #25) Day-To-Night Midi Dress

Remember the Staud blue toile mini dress? Well, this is the same dress in black and in the midi length! Erin loves this dress style so much, she has it in multiple colors, patterns, and lengths. The silhouette is SO flattering and the square neckline is unexpected. Plus, you can wear a regular bra with it…win! Erin wore the dress with the same black Prada bag, but as a belt bag around her waist. She threw on some sneakers and a hat for the day but could easily style it for nighttime with a change of shoes.

L’Agence satin tank dress

Outfit #26) Elevated Event

Next up is this gorgeous L’Agence satin tank dress. The tank dress silhouette makes it feel slightly more casual, but the satin material feels more elevated. The pink and lemon print is so beautiful and fun. Erin bought this to wear to dinner at a restaurant where you dine beneath lemon trees but ended up going with something different. You could easily wear this to a nice dinner or an event.

Which of these outfits was your favorite? Let us know in the comments below! We always love hearing from you!

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9 thoughts on “These 20+ Italy Outfits Will Have You Dreaming of an Italian Summer Getaway

  1. Some of these are great, but I think wearing a dress that looks transparent to the Vatican is a bit disrespectful. I know it’s lined, but the intended effect (especially from afar) is that it’s completely sheer. I’m not even a Christian, but I think this is too much for visiting a place that is holy to millions of people.

    1. I respectfully disagree. I think this dress is beautiful, elegant and very tasteful. It reminds me of my first communion and confirmation dresses… somehow wearing white in such a holy place felt like a perfect choice.

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