Italy Is For Outfit Romantics

What I wore for five days of decadence in Emilia Romania.

May 05, 2025

This week’s post is free thanks to Veronica Beard.

Last week I was lucky enough to jet-set my way on over to Italy for a five day taste of la dolce vita. Technically it was a work trip, but as I was there with an Italian alcohol brand, work felt a whole lot like play (more on that later). It sounds weird, but I love packing for vacations because I get to explore a different version of my personal style. I don’t cosplay, but I don’t really stick to what I’d wear at home either. I’m expressing myself through the lens of where I’m headed and who I want to be when I’m there.

For Italy, my vibe was soft and romantic, ditching anything too stiff or edgy and embracing eyelet, gingham, and linen for a more gossamer touch. In the heart of Emilia Romagna (which shares its root with my name — Aemilia is the ancient Roman spelling), I envisioned myself basking in the same golden light as Call Me By Your Name or Under The Tuscan Sun while strolling outside and enjoying a spritz. Sadly, I wasn’t mistaken for an Italian pop star, but another editor on the trip told me that my looks throughout the week were giving him vintage Lauren Hutton vibes, and I will gladly take that compliment and run with it.

I packed pieces that were easy to mix and match, knowing that I’d be swapping things around for different activities and as I went from day (eating and drinking) to evening (more eating and drinking). But, it wasn’t just about being practical, it’s delightful to walk around a beautiful place in beautiful clothes. On social media, there’s a trend about romanticizing your life — finding ways to fall in love with the everyday routines. In Italy, I was busy romanticizing my style, finding an unreasonable joy in dressing up for something as simple as a walk through a beautiful place. Below, find both a rundown of what I wore, but also what I bought, ate, and drank as I made my way through Bologna and Venice.

Day 1: A Visit to Montenegro HQ

Wearing: Madewell Ruffled Top $98, J.Crew x Araks Underwire Bra $145, Boyish Ziggy Jeans $80 via Poshmark, Madewell Sandals $148.

Fresh off the plane, I threw down my things at Grand Hotel Majestic Gia Baglioni, an old school Italian hotel with an insane breakfast spread and ornate decor. One morning I got lost looking for a bathroom and found myself in the basement which had an ancient Roman road revealed to those who stumbled upon it.

I grabbed an insane roast beef sandwich for lunch from Salumeria Simoni. It feels very Italian to stumble into a random restaurant and have one of the best meals you’ve had in months and Bologna is full of windy little streets that let you stumble upon something aesthetic or delicious. We headed to Montenegro HQ to learn more about the making of amaro and to kick off the week with a Montenegro tasting. I topped my outfit with a disposable lab coat and high-vis vest as we toured and sipped.

Day 1: Dinner at Rodrigo

Wearing: Chava Studio Infinity Collar Shirt $470, Boyish Ziggy Jeans $80 via Poshmark, Madewell Western Belt $68.

This shirt is from Chava my friend Olivia’s brand and was made to my measurements. I love the big, stiff cuffs for a dramatic effect. I was worried about getting wine and pasta sauce on such a pristine white shirt, but I managed to survive stain free thanks to very restrained pasta twirling. My first dinner in Bologna involved cured meats, a homemade bolognese (which they do not call it in Bologna, it is simply ragú) and a carciofi salad of thinly-sliced artichoke and orange slices. Rodrigo is a classic restaurant in town and every course was delicious and rich, the idealized Italian feast. Lambrusco is the local wine specialty, and also a current favorite of mine, so I was excited to enjoy it alongside the meal.

Day 2: Parmesan & Balsamic Tastings

Wearing: Argent x Citizens of Humanity Isabel Tank $98, Donni Linen Simple Pants $168, Adidas x Wales Bonner sneakers, Dunst suede jacket (similar from Cos $690), Wandler bag $985.

I spent my first full day in Bologna diving right in to eating and drinking (of course). My outfit was simple, but these stretchy-waisted Donni pants have become a staple for packing because they’re lightweight, comfy in warm weather, and can get a little wrinkly without it looking bad. My Wandler bag is my current favorite crossbody, and I’m loving the look of a collared suede jacket for transitional weather, because it goes with both my more tailored work stuff and the floaty dresses I packed on vacay.

We started off by touring a parmesan factory where I got to see cheese making in action and sample the crusty, crystallized goods. Wheels of parmesan are stored in a giant warehouse to age, and apparently they have a James Bond-level security system since it’s tens of millions of dollars worth of cheese. Can you imagine a cheese heist film in the style of The Italian Job? I’d watch that.

We also went to a balsamic vinegar farm for a tasting, led by the very cute and very Italian 4th generation balsamic maker. It sounds silly, but I learned a lot about the difference between the swill I buy from Trader Joe’s and what a real aged balsamic tastes like. It was thick and syrupy, sweet enough that I envisioned drizzling it over vanilla ice cream. It’s a seemingly convoluted process to make it, and a real labor of love. I’m a sucker for small family business stories that do it the right way, forgoing money and growth for the love of the process so I was hooked (you know I bought some to take home with me).

Day 2: Dinner at I Portici

Wearing: Veronica Beard Gemma Dress $698, Tory Burch Romy Bag $348, Maryam Nassir Zadeh x J.Crew Block Sandals $129.

Dinner on night two involved visiting the private dining room of Michelin star restaurant I Portici which was housed in an ancient cistern with a glass floor to the current wine cellar below. This long-sleeve silky dress from Veronica Beard was the right amount of fancy. I’m generally not one for floral prints, but I like paisley as an alternative that’s colorful and graphic but doesn’t feel overly girly (if you want to nerd out, I highly recommend this Articles of Interest episode on the print). I dined on tortellini and a funny chocolate mousse shaped like a raspberry, and I drank a whole lot of amaro. Not complaining!

Day 3: Driving A Sports Car Through The Hills

Wearing: Veronica Beard Lois Vest $548 and Haina Shorts $378, Kowtow denim jacket (old, but I like this one from the brand $249, or this one from Alex Mill is similarly boxy $135), Cartier watch , Ancient Greek Sandals Estia $265, Tory Burch Romy Bag $348, Cubitts Frith Sunglasses $200.

As a fair weather F1 watcher (and Lewis Hamilton fan), when I heard I was going to take a Ferrari for a spin through the hills of Modena and Parma, I was ready to channel my inner race car driver. In New York traffic I’m a passenger princess, but I actually enjoy being behind the wheel on scenic drives where I can whip around corners, smelling the trees and fields as we pass by.

It was sunny and warm, so this playful gingham matching set from Veronica Beard was the right balance of comfy and cute for the occasion. A silk scarf tied under the chin felt a little too on the nose, but I think a headband covers the same ground in a more modern way. I got in a little trouble when I got in the driver’s seat of the Lambo and floored it (my stomach dropped like I was on a roller coaster), but in the end the Italians running the super car operation told me I was a good driver, so no harm no foul. Che figata!

Day 3: Drinks At Bar Volare

Wearing: Veronica Beard Lois Vest $548, Boyish Ziggy Carpenter Jeans, Chanel Flats $545 via The Real Real, Dunce jacket, Tory Burch Romy Bag $348, Completedworks Thread Earrings $307.

When I got home to change for the evening, I kept my vest on, but swapped the rest of my look for a more casual night-out vibe complete with jeans, flats, and the suede jacket. We were climbing a dozen sets of stairs and ladders to get to the top of one of Bologna’s signature towers for a nightcap, so I didn’t want to wear anything too fussy or be at risk of flashing anyone below me.

Pre-climb, we went to Bar Volare, a local spot that specializes in twists on classic cocktails, where the owner Pepe made us a selection of his favorites including my favorite, the herbaceous Amore Amaro which he topped with a bay leaf.

Day 4: Sightseeing In Venice

Wearing: Doen Leslie Dress $298, Barrie sweater (similar on Vestiaire for $242, Baserange Socks $30, Salomon Moc Sneakers $100, Tory Burch Romy Bag $348, Ferragamo sunglasses (similar on TRR for $122).

When I first got to Venice, we spent a few hours strolling the city to get a feel for its landmarks and to taste cicchetti, the city’s signature bites and sip on Select spritzes. It wasn’t warm enough for a jacket, so I wore this Gingham Doen dress with an old Barrie sweater tied over my shoulders just in case. Since we were walking on cobblestones, practical footwear won out over something more sleek. My slip-on Salomons are the perfect travel shoe because they’re shockingly lightweight (almost like wearing a slipper).

I didn’t have high expectations for Venice, I anticipated it to be something like Disneyland — and while the tourists were a little much, I was so pleasantly surprised by how magical the city felt when you could sneak into the quiet corners. The architecture is grand, but has a worn-in feel, with laundry flapping from the windows and wisteria vines twisting up gutters. It was all very romantic, and hopping on a water taxi made me feel like a celeb in full glam making a grand entrance at the Venice Film Festival.

Day 4: Dinner At the Aman in Venice

Wearing: Veronica Beard Aven Dress $598 , Baserange Socks $30, Maryam Nassir Zadeh x J.Crew Block Sandals $129, CRZM by Mociun Bedrock Necklace $1750, Jenny Bird bracelet, Carolina Bucci Forte Bracelet $630, Tuza hoops (similar from Jennifer Fisher $161, Ferragamo sunglasses (similar on TRR for $122).

For dinner I got the chance to visit the Aman hotel in Venice, which is located in a palazzo on the grand canal (the family who owns it still lives upstairs — nice). Over a dinner of langoustine risotto, we played a boisterous game of fuck, marry, kill involving chocolate, ice cream, and cheese (marry chocolate, fuck ice cream, kill cheese…sorry!). I’m a sucker for beautiful old homes, so I couldn’t stop myself from taking photos of every detail from the painted ceilings to the original bubbly glass in the library.

This white eyelet dress felt appropriately summery for the warm weather, and I styled it with a few quirky little details to keep it from feeling too pristine. A mix of chunky silver and colorful jewelry added edge, while wearing pink socks with my heeled sandals felt like an unexpected little style surprise since I’d already worn the heels a few times during the trip.

Day 5: Visiting The Peggy Guggenheim Museum and shopping at Prada

Wearing: Argent x Citizens of Humanity Isabel Tank $98, Donni Linen Simple Pants $168, Adidas x Wales Bonner sneakers, Wandler bag $985, Ferragamo sunglasses (similar on TRR for $122).

On my last day, I had some free time to explore Venice on my own. It was hot and sunny, and I was dressed for strolling — sneakers, my linen pants, and a tank. I started with a visit to the Peggy Guggenheim Collection, an insane selection of pieces from Calder, Dalí, Picasso, Magritte, Klee etc. etc. all from her personal archive and shown in her former home along the canal. After visiting, I added Peggy’s autobiography to my future reading list — she seems like quite a character, and a woman ahead of her time.

After my visit, I spent the afternoon getting lost, visiting vintage shops and of course, stopping by the Prada store to ponder making a purchase since it’s cheaper than in the states. Ultimately, I struck out (the current economy has me hesitant to drop thousands of dollars in one place), but still had fun picking out the pieces to try on that I’d been eying since I first saw them on the runway.

What I Brought Home:

After my trip, I came home with a few goodies, nothing crazy just a couple of fun bits and bobs!! I tasted this vinegar at the balsamic farm, it was infused with mint and rosemary and was so sweet and unexpected, perfect for summer salads. I also popped into the Fabri store and since I already have the Amarena cherries at home (my favorite for ice cream and cocktails) I brought home a pistachio cream for morning toast instead. Lastly, after touring the Wave Murano glass factory (they were working on upcoming projects for Bottega Veneta and Zegna if that tells you anything about the vibe) I picked up four water glasses so I can finally give away the mason jars I’ve been using.