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17 Real Outfits I Wore in Italy

HAPPY MONDAY everybody!

We had the best weekend visiting our family friends up in Lake Geneva! Have you been? It’s so beautiful up there and it’s the perfect weekend getaway from Chicago (speaking of, if you’re looking to get out of the city, I did a whole roundup of Chicago weekend getaways in this post!)

I hope you enjoyed my Italy Packing List post that was published on Friday (thanks for being patient with me while I finished it!) I thought a great follow up to that post would be a recap of the outfits I wore in Italy according to my iPhone! In all honesty I feel like “real outfits” isn’t even the right term–I don’t shoot outfits that aren’t “real outfits” ? but, you know, I feel like it’s always more reassuring to see outfits captured “in the wild” ?

Here are 17 outfits that I wore on our Italy trip, snapped courtesy of Neal, with my iPhone ?

Snapped at O’Hare before our flight! Old striped tee, Yoga Pants, Allbirds, Lo & Sons Catalina Deluxe Tote, Delsey Suitcase (See above note!)  

Everlane Box Cut tee and Abercrombie Jean Shorts

Our first stop in Florence was showing Neal my old apartment! 14 Via Dante Alighieri! Wearing my Everlane Box Cut tee (comes in tons of colors!), Abercrombie Jean Shorts (this was the only time I wore my jean shorts if we’re being honest) Old sandals

Everlane Box Cut tee and white Everlane denin skirt

Our first night in Florence, enjoying a bottle of prosecco on the rooftop of our hotel–The Glance–would highly recommend staying there! Wearing the same Everlane tee but changed into my white Everlane denim skirt and salvaged my hair with a scarf (mine is vintage, but similar here!) for dinner at Il Gato e la Volpe (one of my old study abroad haunts–its so great. Ask for Fatjon!)

Everlane t-shirt dress, Straw boater hat, Madewell backpack, Jack Purcell sneakers

Posing in front of the Duomo before a day of exploring the city. Wearing my Everlane t-shirt dress, Straw boater hat, Madewell backpackJack Purcell sneakers

my favorite striped Linen Midi Dress

Heading out to dinner at Za Za, one of my favorite restaurants in Florence! You must get the truffle pasta! Wearing my favorite striped Linen Midi Dress, old Kendra Scott Earrings

Everlane Japanese Go-Weave Camisole, white Everlane denim skirt,

My first taste of Antico Noe in TEN YEARS! The best sandwich shop in Florence (we went twice!) You must get the #4! Wearing Everlane Japanese Go-Weave Camisolewhite Everlane denim skirt, similar scarf

Everlane Japanese Go-Weave Camisole, white Everlane denim skirt,

Admiring the sunset at Piazza Michelangelo! Wearing Everlane Japanese Go-Weave Camisole,white Everlane denim skirt, Madewell backpacksimilar scarf, old sandals

Jack Purcell sneakers

Heading out to explore in Florence. Wearing this midi dress AGAIN with my Jack Purcell sneakers

ASOS striped mini dress, Steven Greece Slide Sandals, Madewell backpack

On the way out to dinner in Florence–wearing my ASOS striped mini dressSteven Greece Slide Sandals, Madewell backpack

Everlane wrap dress,

Wine tasting in San Gimignano wearing my Everlane wrap dress, Scarf from the Florence leather markets, similar scarf here.

Everlane t-shirt dress and Steven Greece Slide Sandals

We took a cooking class with Nonna Ciana in Tuscany and it was one of our favorite parts of the trip! Here I’m wearing (yet again) my Everlane t-shirt dress and Steven Greece Slide Sandals

Everlane Cotton Midi Dress

Sunset in the Tuscan vineyards at Borgo San Felice, wearing my Everlane Cotton Midi Dress (TTS but now sold out in navy, but available in stripes!) Steven Greece Slide Sandals

Abercrombie black bikini, Everlane shirt dress,

AHH take me back to the gorgeous pool at Borgo San Felice in Tuscany! Here I’m wearing my Abercrombie black bikini, Everlane shirt dress, similar straw hat, and of course (although not pictured) the Steven Greece Slide Sandals.

WAYF dress

Wore this WAYF dress to Capri (sold out) but very similar Reformation dress here, and Steven Greece Slide Sandals

linen polka dot mini

On the water Taxi to Amalfi and then Ravello (see my guide on the Amalfi Coast here!)–Wore my linen polka dot mini (sold out, but Reformation carries a TON of cute versions that are similar in cut!) I also love this one that is gingham and ties in the back as well as this little retro striped one! This green linen mini is perfect as well. All look so cute with sandals OR sneakers!  Madewell backpack.

Madewell shorts, similar linen shirt,  Madewell backpack, Jack Purcell sneakers

In Pompeii (this was thought to be the first “fast casual” pizza oven ever created! So cool right!?) Madewell shorts, similar linen shirt, similar hatMadewell backpackJack Purcell sneakers

 Madewell shorts, Everlane Air Camisole

In Rome on our favorite tour ever–Eating Italy’s “Taste of Testaccio” tour–eating Suppli (Roman deep fried risotto balls, similar to Arancini!) wearing Madewell shorts, Everlane Air Camisole, Allbirds, Madewell backpack

For more details on what I packed for our trip, make sure to see my big Packing for Italy guide and also What to Wear in Tuscany, Amalfi Coast Guide, and 30+ Insider Tips You Need to Know Before Traveling to Italy