13 Perfect Looks to Pack if You’re Going to Tuscany or Want to Emulate Italian Summer Style — From $10

As a travel editor who’s been to more than 40 countries, I’ve seen a lot of the world — but I still haven’t found anywhere that compares to Italy in the summer. My sun-kissed memories of cruising around Capri, leather-shopping in Florence, and bike riding through Chianti vineyards are some of my fondest, which is why I can’t wait to get back there in May. This time I’ll be focusing on Tuscany, and you can bet that I plan to live out my dreams of lounging by the villa pool with a spritz in hand.

Of course, I’m going to need a wardrobe that lives up to the glam of this trip (but that fits in a carry-on since I haven’t checked a bag in four-plus years, and I’m not about to start now). With past Italy visits under my belt, I already know I’ll need comfortable walking shoes and a breezy sundress, but I’m adding a few new looks to my suitcase, including wide-leg pants and a matching set. Here’s what I’m eyeing for my trip to Italy — and hopefully, it’ll inspire all of your out-of-office adventures near and far, too.

The Perfect Sundress

I can see it now: I’m walking through Florence with a gelato and admiring the Duomo, wearing the perfect sundress. For this, I’ve already picked up the Melody Smocked Midi Dress from Madewell in black knowing it’ll take me from day to night — city walk to aperitivo — effortlessly. Thanks to its ultra-flattering fit with a smocked top and gentle A-line flare, I wouldn’t doubt if you see this midi dress way beyond Italy this summer. I’m going to pair it with white sneakers during the day and my platform sandals in the evening. I’m also eyeing this beautiful white sundress and this aptly named “Tagliatelle” dress from Reformation.

Comfortable White Sneakers

I’ve been a loyal fan of the celeb-loved Veja Campo sneakers for years now, but after reading rave reviews of these cushioned, platform Dr. Scholl’s Time Off Sneakers, I may just make the upgrade before my trip. Even Oprah loves this brand, with shoppers saying they feel like “walking on clouds.” Sounds like they’re worth it, especially since they’re on sale. I plan to wear these with everything from my breezy sundresses to casual shorts. 

Leather Crossbody Bag

It’s practically shameful to walk through Florence’s leather market without your own nice leather bag, and this one from Lo & Sons recently changed my world. The stylish, versatile Lo & Sons Waverley 2 4-in-1 Bag has a convertible strap that makes it four bags in one. I can wear it on my shoulder, crossbody for more security, as a belt bag to keep my hands free, and as a wristlet for a night out. That covers pretty much everything on my itinerary — and cuts down on packing space.

Tailored Shorts

These high-waisted shorts are so classy and elegant, they practically scream “Italy vacation.” French-girl-favorite and T+L editor-loved brand Sézane must’ve thought so too because they named this style “Rome.” I love the elevated, tailored details like pleating and cuffs. For the same look for less, I’d spring for these casual $26 linen shorts or classic $25 white shorts from Amazon.

Oversized White Button-down Shirt

I’m convinced there’s no trip I can’t use this Hotouch oversized white button-down shirt for, which is why it’s a permanent part of my travel capsule wardrobe. I can use it to cover up in the morning or evening if it’s chilly or if I enter a church, or I can throw it on over a bathing suit by the villa pool in Tuscany. (Psst, you can shop more of our favorite oversized button-downs here!)

Silk Scarf

Maybe it’s the White Lotus Tanya McQuoid in me, but I can’t imagine my Italy trip without a silk scarf to tie around my neck or hair (while riding a Vespa, probably). I’m eyeing this pretty, neutral one from Fonyve from Amazon since it’s a steal at $10. I was sold the moment I read this five-star review from a fellow traveler: “Elegant, well-made scarf…The colors of these are very vibrant and look like expensive scarves from Italy.” 

Sunglasses

I always had a lot of trouble finding sunglasses that fit my narrow face (I used to buy kids’ sizes!) — until I tried these frames at Warby Parker, the same affordable brand that makes my eyeglasses. I love that they have narrow, medium, and wide sizes to fit pretty much any face, and you can add polarization and your prescription to them, all for way less than you’d normally pay for name-brand sunglasses. There’s far less guilt than if I lost my Ray-Bans, but they’re still nicer than super cheap ones. If you’re still not ready to shell out $95 for a quality pair, you can’t go wrong with these Sojos vintage sunglasses at Amazon, which look just like them but are only $15. 

Wide-leg White Linen Pants

I’ve written before about how Madewell’s Harlow wide-leg pants are the comfiest pants I own and go with absolutely everything (I even purchased another color after originally buying them), but I’ll sing their praises again and again. They are made from a luxuriously soft lyocell-linen blend that keeps things cool even on hot days, and I’ve found they wrinkle far less than my 100 percent linen pants.

Thin Leather Belt

Sometimes crafting the perfect travel outfit is all about accessories, and the right belt can take a good outfit from good to bellissima. This thin, understated option from Jasgood adds just the right amount of polish to a look whether it’s cinching a billowy dress or adding the cherry on top of the perfect pants. Adding a belt is also great for switching up looks from day to day.

Cardigan Sweater

Nights can get chilly in the Tuscan hills — even June and July see lows of 60 degrees Fahrenheit. That’s why I pack a versatile cardigan that pairs with all my looks in case I get cold. To pass my Italy packing list test, I usually ask myself, “Would Audrey Hepburn have worn this?” And this one from J. Crew passed the test. There’s something decidedly European about its classic stripes, and its neutral palette will match with anything I pack. While the 100 percent cotton sweater is on sale for less than $100 (and has an impressive 4.7 rating), I found a more affordable lookalike at Amazon for just $40.

Matching Set

Matching sets are the epitome of no-fuss, one-and-done outfits that look put-together for any event on the itinerary, whether you’re sipping Chianti at a vineyard or exploring town. Plus, you can mix and match them with other shorts and tops in your suitcase for maximum outfit potential. I splurged on the Noah Two-piece Set from Reformation (look how perfect that “linguini” print is for an Italian wedding weekend event!) but I also have and would recommend something very similar to this $33 matching set from Amazon.

Wide-brim Packable Sun Hat

I plan to soak up the Tuscan sun on this trip and to make sure I’m protected and looking stylish, I’ll pack my trusty J.Crew Packable Sun Hat that’s taken me from Egypt to Greece and back. It easily folds right up into my carry-on, and only takes minimal zhuzhing to get back to its original shape. I’d snap one up while they’re still 62 percent off if I were you.

High-waist Yoga Shorts

One of the most magical moments of my last trips to Tuscany was a bike ride through Chianti. I’m planning to convince my travel partners to re-create that, and I know for that I’ll need some athletic shorts like this pair I swear by from The Gym People. They’re perfect when strolling through markets paired with my oversized white button-down, sun hat, and sneakers. 

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