Everything I Wore in Italy.

Everything I Wore in Italy

As I packed for Venice, I had a very specific vision in my head. A mix of Sofia Richie and Marge from The Talented Mr. Ripley, with maybe a little more color. I didn’t really think about the weather until the week before the trip when I realized we would be looking at high 50s, low 60s, and lots of rain. I chatted with a girlfriend who had just gotten back from London and had the same issue (do you pack for the weather or for the outfits?) and she said, “Just pack the outfits! You can always just uber or take a taxi” That is what I did.. except.. Venice is unique in that there are no cars on the island. There really isn’t a practical way to get around besides walking or the Vaporetto (Venice’s water bus).

I wish that someone would have shaken me before we left and said, “Grace: there are no cars in Venice so you will either be walking or taking public transportation (a boat). Pack warm, comfortable clothes!” And along those lines, it isn’t leisure walking: there are so many stairs, wobbly cobblestone streets, and little bridges. The walks are amazing but not in high heels. So maybe this is helpful to you if you are reading this and have never been to Venice. Learn from my mistakes. Wear sneakers!

Everything I Wore in Italy

Stilettos were an absolute NO, and while I did wear my chunky platforms quite a bit, by Thursday (we clocked 20,000 steps that day and were out past 2am), my knees were shot and I relegated myself to my orange dad sandals for the rest of the trip. You just have to laugh. Over pizza on the street, my boyfriend caught me looking out toward the street, looking wistfully at a group of women wearing cropped jeans, cute tees + sweaters, trenches, and fun sneakers who had just rolled by. He knew what I was thinking. We just looked at each other and started laughing. The outfits!!!

And so: I am not a beacon of Italian style. But I had a great time. And by Friday it had warmed up a little bit and I liked those outfits. It just is what it is. I looked like a mess for a part of it (I didn’t document the really bad outfits here) but it will always be one of my all time favorite trips. I hope to go back again someday (and when I do, I’ll pack all my cutest sneakers!).

Venice fancy dinner outfit
Dinner at Da Ivo

On our first night, we had reservations at Da Ivo (full roundup of everything we ate/drank/did coming at you next week but Da Ivo is a celebrity favorite) so I thought I would be fancy. I wore this Pucci dress. I had originally packed these gold sandals to wear with it but quickly realized I’d be walking a mile (+ up and over bridges and through Venice’s twisty side streets). So I wore my See by Chloe platforms instead. These are shockingly comfortable and were fine for the night but my feet did hurt. I am also wearing this Blaze Milano blazer (currently on sale!) and this Prada bag. The blazer doesn’t really go but it was cuter than my raincoat and I would have frozen without it.

3 carat white silver earrings

I packed a lot of Dorsey for this trip. These earrings are incredible. Three carats of lab-grown sapphire that could easily pass for diamonds. They’re a great price too.

Everything I Wore in Italy
rainy day outfit in Italy
Rainy day outfit

The next day was extremely rainy. I wore my AGOLDE white jeans, the softest sweater from Kilte (truly the BEST), my Vince Warren platforms and a Loro Piana rain coat from ten or eleven years ago.

Veronica Beard dress
Another fancy dinner

For dinner that night (our other very fancy meal — the tasting menu at Da Fiore), I wore this pink Veronica Beard dress. As with the Pucci dress it was meant to be worn with the gold stilettos but packing stilettos for Venice is a fail. I wore the platforms.

Dorsey drop earrings

(And another stunning pair of Dorsey earrings. A few of you told me you got these for your wedding, I think that is a great move. So so sparkly)

Gucci dress | Everything I Wore in Italy
Gucci dress

The piece I was most excited to wear was this Gucci dress, a steal from The RealReal. I was shocked to find it new with tags, in my size, for less than 1/4 the original price since it was missing a belt.


I do really love this blazer. In hindsight a trench would have looked better with both dresses. But I was excited to wear it and packed it.

white sapphire drop earrings

And these earrings again.

Italy sightseeing outfit
For sightseeing

This Patou jacket (a favorite), AGOLDE Jeans, the orange dad sandals.

Everything I Wore in Italy

I know the sunglasses make me look a little crazy but I LOVE them. They felt apropos for Peggy Guggenheim. Amazon version here!

Everything I Wore in Italy

I felt like myself in this… on our last day, when it was warm! I was comfortable and happy. My Ganni dress (size down), the Patou jacket, the orange dad sandals. Perfect for a long but fun day roaming the Biennale.

Venice Biennale 2023

Disclosure: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature things I truly love here. Thanks for your support.

Leave a Comment

Leave a Comment


  1. Oh no! Packing “fails” are never fun in the moment, but they make for the very best stories after the fact. There’s really nothing better than an excuse to go back, right?

    5.24.23 Reply
  2. Whitney:

    Obsessed with your Patou jacket!

    5.25.23 Reply
  3. Lisa:

    I LOVE LOVE Venice! One of my favorite places ever. I just love the quaint-ness and romantic charm of all the roads/canals/bridges/cafes, etc. On a two week trip to Ireland/England I made a shoe packing error and have never bought new shoes faster. Sure, they were expensive in the moment but I was so thankful for them. Glad you had a great time!

    5.25.23 Reply
  4. Vicki:

    A few years ago I went to the north of England in August. I’m from the US East Coast so I packed a bunch of summery items and a cardigan and a sweatshirt for the plane. The warmest day was in the low 60’s and most days it rained and was chilly. I froze the whole time and wound up living in my jeans, sweatshirt, and the one pair of closed toed shoes I had brought. I hated all my outfits but I still had an amazing time. Now I know better! lol

    5.26.23 Reply
    • Hahaha, that was me!!!! The important thing is that we still had an amazing time 🙂

      5.26.23 Reply
  5. Kate:

    Pitou and dad sandals for the win!
    When you arrive somewhere, do you immediately get to steaming or ironing, or handle day by day? Do you pack your own? I hate wasting the time but love a fresh de-wrinkled fit.

    5.27.23 Reply