What I Wore in Florence (aka When I Chose Fashion Over Function—and Still Had the Time of My Life)
July 2025
This trip was part anniversary celebration, part birthday trip, and very much overdue. From July 25–29, Brant and I slipped away to Florence, Italy to celebrate 19 years of marriage and my 45th birthday. And I’m not going to lie, it felt like a dream. We hadn’t had uninterrupted time together like this in ages, and this trip gave us the space to reconnect, eat amazing food, explore beautiful places, and just breathe. I mean, what better way to spend your mid-40s than eating pasta, drinking wine, and biking through Florence with the love of your life? (Even if that bike ride nearly sent me into a panic attack. We’ll get there.)
We started with a red-eye flight out of Anchorage, spent one night at the TWA Hotel in New York, and then made our way to Florence for four full days of exploring, eating, and soaking in every second of Italian summer. I packed light—just my BEIS carry-on and Mini Weekender and somehow managed to wear every single outfit I packed. Honestly? I felt great in what I wore. It wasn’t perfect (I definitely chose fashion over function again), but I felt confident, comfortable, and fully present.
So here it is—what I wore in Italy. Every outfit, every moment, and a few lessons I learned along the way. Let’s go.
Wednesday/Thursday – Travel Day Comfort
Vibe: Cozy, casual, carry-on queen
This was my go-to travel look for getting from Anchorage to Florence and it definitely put in the miles. I left Wednesday night in an oversized button-up denim shirt (XL) from Target layered over my favorite Vuori black joggers (L), plus my trusty Archies flip-flops for foot support through all the airport sprints and long-haul flights. I threw it right back on after a shower at the TWA Hotel for our flight to Europe because when you find a travel outfit that works, you don’t mess with it. My BEIS mini weekender and 21” carry-on were perfect for packing light and staying organized across multiple flights and a layover in Paris.
Friday Night – Dinner + Karaoke in Florence
Vibe: Chic, classic, Spritz-fueled glam
After a quick nap and a much-needed shower at the hotel, I changed into this black halter dress (L - a new-to-me Target find!) for our first night out in Florence. I paired it with black Open Edit kitten heel slides and carried my mini black Tory Burch bucket bag for the essentials. This was the night of that dinner — the one that ruined us for all future Italian meals, followed by karaoke and maybe one too many Aperol spritzes. Worth it.
Saturday – Exploring Florence + Dinner at Zaza
Vibe: Easy, breezy, scam-prevention chic
Saturday started slow (thank goodness) after a few jam-packed days, and I wanted something simple, breathable, and cute for wandering Florence without overthinking it. I wore an Old Navy black scoop neck tank (XL) with matching black pull-on linen shorts (L), layered under a sleeveless, collarless mushroom-colored vest from Open Edit (L)—which instantly made the look feel more put-together without adding bulk or heat. I added my black Tory Burch bucket bag and wore it crossbody with the strap tight and the bag front and center because I refused to be pickpocketed. Steve Madden sandals carried me all day as we explored the city and eventually had dinner at Za Za that night (highly recommended but didn’t live up to the hype IMO). The outfit was simple, functional, and Florence-ready… even if I was slightly sweaty and very protective of my bag.
Sunday – Bikes, Breakfast, and David (aka: My Panic Attack in Florence)
Vibe: Black on black, with a touch of bike-induced terror
We kicked off Sunday with a very ambitious plan to rent bikes and ride through Florence to breakfast. What started as “this will be cute” quickly turned into me white-knuckling the handlebars, dodging buses, Vespas, and locals who clearly do this daily. Let’s just say I earned that breakfast. Afterward, we went on our tour to see the Statue of David—and yes, he lives up to the hype.
I kept it sleek and simple with a ribbed black cap sleeve tee from American Eagle (sold out, but I linked similar) and a black linen skort from Open Edit (L). Black on black was the theme of the day—practical, easy, and heat-friendly. I wore my black Archies flip-flops (because my feet needed grace), my go-to Tory Burch bucket bag crossbody (again, safety first), and broke in my new prescription sunglasses from Eye Buy Direct. The outfit was perfect for a day that started with chaos and ended with Renaissance art. Balance, right?
Later that evening…
After our morning bike ride adventure and a solid nap back at the hotel (because exhaustion), we cleaned up and headed out to explore the Oltrarno side of Florence and grab dinner. I wore a silky brown ruffle maxi dress from Old Navy that’s sadly sold out—but even if it wasn’t, we didn’t exactly get “the shot.” My shapewear made an unexpected guest appearance (thin dress problems), and my face looked as tired as I felt. The dress was cute, but the outfit didn’t do me any favors—and that’s just real life. Not every look is a win, but the memories still are.
Monday – Tuscany Tour + My Regretfully Cute Shoes
Vibe: Wine country whimsy meets blistered tourist chic
Monday was our last full day in Italy, and we packed it full—bus tour style. I wore a white v-neck spaghetti strap maxi dress (L) from Target that I picked up the morning we left for Italy, because that’s the kind of chaos I thrive in. Brant and I made a quick Target run before the airport—he grabbed linen shirts, I found this dress and a black halter one (because naturally I needed just a couple more options). Paired it with my Steve Madden flats and thought I nailed the effortless Tuscan look. Spoiler alert: I did not nail the footwear choice.
We explored Siena, wandered through a stunning gothic cathedral, hit a vineyard for wine tasting, and made a stop in San Gimignano for what’s supposedly the best gelato in the world (no notes—100% accurate). Our final stop? Pisa. We climbed all 250 stairs to the top of the Leaning Tower, and let me tell you, I regretted every step in those flats. Fashion over function failed me hard that day—but hey, the photos looked great, and I somehow didn’t fall off the tower
Tuesday – Travel Day Home (aka: Just Let Me Sleep)
Vibe: Comfy, covered, and completely exhausted
Our travel home started bright and early with a 6 a.m. departure out of Florence, a quick 45-minute flight to Rome, a layover, and then a 10-hour haul to JFK. I knew comfort was key, so I pulled on my go-to travel staples: a Madewell cropped white tee (XL), black Spanx Air Essentials wide leg pants (XL), and my Lululemon Effortless jacket (size 14). Archies on my feet for support, sunglasses on my face to hide the exhaustion—it wasn’t glamorous, but it got the job done.
This outfit was exactly what I needed for long flights, a long layover, and just trying to survive international travel with my sanity intact. Zero regrets. Maximum comfort.
Wednesday – One More Flight (and One More Outfit)
Vibe: Scrappy, stripey, and out of clean clothes
After landing at JFK on Tuesday, we spent the night at my sister-in-law and brother-in-law’s apartment in Queens. I passed out immediately on their bed—no shame—and we had a low-key dinner with them that night before flying out the next morning.
By Wednesday, I was running low on clean clothes (as in, nothing was washed and I had zero energy to care). I wore a navy scoop neck tank from Old Navy (L) with white linen pants from Gap that had navy stripes (L). I layered on the same Lululemon Effortless jacket (14) for warmth and, even though my Archies would’ve been way more comfortable, I went with the Steve Madden flats because they just looked better with the outfit. I sat for most of the flight anyway, so it was fine. As always, I had my BEIS carry-on and Mini Weekender in tow—those two bags truly carried me through the entire trip.
The Takeaway?
This trip wasn’t about the outfits (though, let’s be honest—I planned them all in my head before we even booked the flights). It wasn’t about the perfect photos or hitting every “must-see” landmark in Florence. It was about time. Uninterrupted time with Brant. After a year of short visits, work travel, and just life getting in the way, this trip gave us a chance to slow down, laugh, get lost, eat incredible food, and just be together.
And that? That was everything.
Yes, I wore the wrong shoes in Pisa. Yes, I got sweaty, tired, and had a few less-than-flattering moments (shout out to my shapewear for trying its best). But I also felt really good in my skin. I felt confident, present, and grateful. Not because everything went perfectly, but because I let go of the pressure for it to be perfect.
The biggest reminder from this trip? Make the time. Take the trip. And don’t save the “good dress” for a day when you feel 100%.
Wear it now. Live it now. Love them now.
Until next time, Italy.