Florida Outfits, Real Life Edition

Four Summer Night Looks

Quick note before we jump in: this post is a little outside my comfort zone. It’s just mirror pics of outfits I actually wore, with a bit of narration along the way. I’ve always felt like everything needed to be perfect before I could share—when, in real life, I don’t actually care about being perfect and I’m very chatty. So I’m trying to lean into that and just show you how I’m putting things together as I go.

If it’s helpful, feel free to tap the ❤️ at the top. It’s always good to know what’s resonating, and it helps more people discover it too. xx

We were in Sarasota last week for USRowing Youth Nationals, which officially wrapped up Maddie’s high school career, and with it, the final chapter of what’s felt like a never-ending season of senior year celebrations.

It’s a long, hot week. The parents are responsible for everything: driving the girls, coordinating dinners, chaperoning, all while trying to keep up with real-life work commitments. It’s definitely not a vacation, but we made the most of the downtime and managed to sneak in a little time alone, which, after the past few weeks, felt like a much-needed reset.

I’m a chronic over-packer with absolutely zero shame about checking a bag for a three-day trip. But this time, with a tight turnaround for our flight home, I committed to just a carry-on and a backpack. Somehow, I packed exactly the right amount for five nights, which turned into six after we were rerouted on the way home.

During the day, I lived in shorts and tanks, and I threw in a swimsuit for quick dips in the hotel pool between activities. But at night, I kept it simple and stuck to dresses. Nothing fussy, just easy, breathable pieces I could throw on and feel pulled together.

I learned last year that I don’t exactly thrive in Florida heat (how these kids race in it all day is beyond me), and anything even slightly clingy is an immediate no. Hair goes up, makeup stays minimal, and comfort mixed with style is the priority.

Here’s what I wore. Some of these pieces might look familiar, and a few were new finds I ordered just for the trip. And if you look closely, you’ll see the slow progression of my sunburn, because no matter how much sunscreen I used, I could not not burn.

We landed on Tuesday and didn’t finish getting the girls settled until late that night, so I spent the entire day in my airport outfit. Not the plan, but it ended up working out just fine.

I always try to wear my bulkiest items on the plane to save space, so I flew in leggings, a lightweight tee, my HOKAs, and a denim jacket, which I took off the second we stepped outside. Not the most exciting outfit, but it was comfortable and freed up a good amount of space in my carry-on.

📍 Wednesday Night – St. Armands Circle

dress, $38 | bag, $13 |shoes, $198

While the girls were at practice, I spent most of Wednesday working from the hotel and honestly, I haven’t had an uninterrupted eight hours to myself in I don’t know how long. It was wonderfully productive and kind of blissful.

That night, we had a free evening and headed to a little bistro in St. Armands Circle. The food was good, the drinks were solid, and it felt nice to stroll around for a bit between rainstorms. After a long travel day and such an emotional, full season, a quiet night was exactly what I needed.

I wore this under-$40 Amazon dress (I’m wearing a small) and packed my $13 go-to woven clutch you might remember from my Miami weekend roundup.

And yes, I wore the Tory Burch Miller sandals. I will die on this hill: they are the best vacation shoe. They take up no space in your bag, go with everything, and double as pool slides. Easy.

You can read my full take on the Miller sandals over on The Well Dressed Life.

📍 Thursday Night – Team Dinner

dress, $39.99 | bag, $13 |shoes, $198

Thursday night was a casual, early team dinner with the girls and their parents, and we got to see so many of our crew friends who were in town.

One of the things I’ve come to love most about rowing is the parent community. You spend a lot of time with these people: super long weekends, travel to regattas, and a surprising amount of just standing around staring at each other. It’s kind of amazing how much I genuinely enjoy being around them. I’m so grateful for the kind, funny, down-to-earth parents this sport has brought into our lives. It makes all the early mornings and hectic weekends feel that much more meaningful.

Longtime readers know I tend to stick to neutrals, but this year, especially as I rebuild my wardrobe, I’ve been sprinkling in a few pieces that fall just outside my usual style.

I ordered this bold printed summer dress (also from Amazon, wearing a small), and I think it’s so fun. It’s stretchy, it moves nicely, and what kind of girl would I be if I wasn’t absolutely delighted by the pockets? It’s even bolder in person—this photo’s a little blurry, but you get the idea.

Also: I stopped for a quick manicure at our hotel, and the young woman checking me in ordered the dress immediately.

That kind of unsolicited validation? The best.

📍 Friday Night – Summer House, Siesta Key

dress, on sale $136.50 | jacket, on sale $79.50 bag, $13 |shoes, $198

Friday night we went to Summer House in Siesta Key. It’s become one of our favorite spots and a must-visit anytime we’re in town. The food is fantastic, the service is always great, and the vibe is that perfect blend of elegant but casual. Basically, it checks all my boxes.

I almost forgot to take a picture, so this was snapped back at the hotel—and you can kind of tell I was starting to hit the I’m ready to go home stage of the trip, I missed my Ava and Vivi so much by now.

I wore this eyelet dress from J.Crew in coral, which is currently 50% off. I’m in the medium, and it’s totally fine, but I probably could’ve gone with the small. I threw on my trusty denim jacket (also J.Crew, also on sale), which became my constant companion all week since every restaurant was freezing.

📍 Saturday Night – Dinner at the Ritz Carlton Sarasota

dress, $39.99 | bag, $13 |shoes, $125

Last year, we had dinner with a group of our parent friends at the restaurant at the Ritz-Carlton, and it turned into one of those unexpectedly perfect nights, so we made it a tradition. We went back again this year, and it was just as lovely.

It felt a little bittersweet. Happily, we still have a few more years with Ava on the team, but for our senior parents, this was their last trip. The restaurant is beautiful, the food is fantastic, and the people-watching? Truly elite.

We laughed, shared stories, and lingered at the table until they were closing up around us. And let’s just say, I was genuinely shocked to wake up feeling completely fine the next morning, especially since I didn’t say no to the Limoncello that was supposed to end the evening, or to the “just one more Prosecco” that followed. 😉

By this point in the trip, the sun had officially won. I made it through a full week in Florida without burning, only to get scorched at the hotel pool. (It’s not as bad as it looks, I swear.)

As for the dress: I love this one shoulder gem I found. I ordered it from Amazon on a last-minute whim, packed it without even trying it on, and it ended up being perfect. It comes with a rope belt that matches the shoulder tie, but I liked the silhouette better without it. Much easier and a little more relaxed and elegant.

I paired it with the Dolce Vita Mylee Heels, which I think instantly elevate the dress and they’re surprisingly comfortable. And Ring Concierge sent me these gorgeous earrings called Swirling Studs. They remind me of little seashells, so they felt just right for a summer night.

And that’s it! I forgot how nice it is to actually have limited options, you know? There’s something oddly satisfying about making it all work with what you packed and not overthinking it.

If you’re heading somewhere warm and want to pack light without feeling like you’re just repeating the same outfit every day, hopefully this gives you a little inspiration.

And if you’re curious about the travel must-haves that helped make it all work, I shared a full roundup over on The Well Dressed Life, you can read it here.

Snapped this quick picture of my bag on the way home. Still organized!

The Travel Essentials That Helped Me Pack Light (and Right)

❤️ Let me know your thoughts in the comments below!