What I Wore in Sarasota: Vacation-Ready Outfits for Milder Weather | Jo-Lynne Shane

10 Days of Outfits for Florida in February

It was freezing when I left Philadelphia, so I layered up with a lightweight sweater and a short trench coat—perfect for staying warm at the airport but easy to shed once I arrived in Florida. I have two suitcases because one was packed with outfits for photoshoots, while the other held my travel capsule for the week. (Of course, there was plenty of overlap, since we photographed all of my actual vacation outfits as well.)

similar trench // stripe sweater (M) // Pistola Kinsley Flares (29) // Paul Green Hadley (8) (option) // Away The Medium // Away The Bigger Carry-On // Away The Everywhere Bag

My photographer, Alison, and I were on the same flight to Sarasota, so we shared an Uber to Lido Beach Resort, where we met up with Deb and Beth. We hit the ground running and spent a few hours shooting outfits that afternoon. Since we hadn’t made dinner reservations, we lucked out and snagged the only high top at the bar at Drift, the very popular restaurant at our hotel.

This was the last outfit I photographed that day, so I just kept it on for dinner. This striped polo-neck sweater is such a great transition piece—lightweight, textured, and made from a breathable cotton blend with a fun multi-directional stripe pattern. Plus, it’s on sale and a great price! The shorter length makes it perfect for pairing with crop jeans, like the PAIGE Nellie, and the warm brown slides create a pleasing contrast to the cooler tones in the outfit. I also like how the rattan earrings add some texture near my face, but sadly, they’re from last year and I can’t find anything quite like them.

LOFT Mixed Stripe Collared Sweater (S) // PAIGE Nellie (29) // Veronica Beard Via (8.5) // old rattan hoops

The next morning, we were up bright and early and back at it. After several hours of shooting, we took a quick break at the poolside Tiki Bar. I originally just wanted a drink to hold for some photos, but it ended up being the perfect excuse to pause for a bit.

FRAME Le Mid Rise V-Neck Tee (XS) (option) // red stripe sweater (M) // similar belt // PAIGE Anessa (29) (option) // Tom Ford sunnies (option) // Anna Beck toggle necklace

From there, we made our way to St. Armand’s Circle for lunch. After walking around for a while (and, yes, taking a few more photos!), we grabbed a table at Cha Cha Coconuts, where we could sit outside and enjoy the live music. (And no, we did NOT plan to be color-coordinated, but how cute did this turn out to be???)

Deb’s top, jeans, bag & necklace // Beth’s jacket, top, skirt, belt & necklace

I wore this crisp blue-and-white pinstripe cropped button-up with white ankle flares and neutral sandals. Then, I stepped out of my comfort zone a bit and threw a chartreuse cardigan over my shoulders for a little pop of color.

stripe button-up // MOTHER Hustler (30) (option) // Veronica Beard Via (8.5) (option) // similar bag // Splendid Dre in Chartreuse (S) // Veronica Beard Via (8.5) // Jenny Bird hoops // Anna Beck toggle necklace

Later in the afternoon, we headed back to the resort to take some photos on the beach. Once the sun set and we ran out of daylight, we returned to St. Armands Circle for dinner at Crab & Fin. It’s more of a white-tablecloth kind of spot, so we dressed up a bit.

I considered wearing the polka dot dress outfit I shared the other day but chickened out and stuck with my comfort zone—this black linen sheath. It’s such a great little dress, easy to dress up or down. I often wear it with sneakers, but for dinner, I opted for metallic leather flip-flops for a lighter look.

Beth’s dress // Deb’s dress ? // my dress // zestt organics Travel Wrap // Freja bag // beek flip flops (8)

Monday was a dreary day. We took some photos in the morning, but by the afternoon, we gave ourselves a little break. Beth and Deb went to the mall, while Alison and I grabbed lunch at the Tiki Bar and then retreated to our rooms to catch up on computer work. I was wearing my Margarita Tee and jeans, so she took a picture… I had to order a Margarita, of course!

MOTHER Margarita Tee (option) // Pistola Kinsley Flares (29) // Paul Green Hadley (8) (option)

Later that afternoon, we took a few more photos before heading back to St. Armands Circle for dinner at Columbia. By then, it was pouring rain, but I didn’t get the memo in time to change into the short trench, which would have offered a little protection. Instead, I just wore the last outfit we photographed. As it turned out, this Frank & Eileen peacoat-style sweatshirt was nice and cozy for the chilly night—and thankfully, our hotel had complimentary umbrellas!

(If you’d like a lower-priced option, the Splendid Diana French Terry Blazer is on sale at Evereve!)

Frank & Eileen Mini Belfast c/o (S) (option) // FRAME Le Mid Rise V-Neck (XS) (option) // similar belt // Paul Green Hadley (8) (option) // similar bag // Jenny Bird earrings // Anna Beck toggle necklace

The next morning, we squeezed in a few last-minute outfit shoots before heading back to our rooms to pack up. Alison, Beth, and Deb were flying home, and I was moving to The Modern, a hotel in downtown Sarasota, where Paul would be meeting me for our vacation.

It was still chilly and a bit dreary, so this time I pulled out my trench coat—partly for warmth, partly to save room in my suitcase(s). This time, I layered it over a navy and white striped sweater and swapped my full-length flares for cropped wide-leg jeans.

similar trench // Faherty sweater (S) (option) // PAIGE Anessa (29) (option) // Paul Green Hadley (8) (option) // old rattan hoops // Anna Beck necklace

Before parting ways, Alison and I had one last lunch at the Tiki Bar. Then, I grabbed an Uber and made my way over to The Modern to meet up with Paul. As soon as we got to our room, I changed into shorts and sandals—the rain had cleared, and it turned into a gorgeous, sunny afternoon!

Faherty sweater (S) (option) // Vineyard Vines shorts (8) // Jeffrey Campbell boat shoes (8.5) // Jenny Bird hoops // similar bag

Spring Travel Capsule Outfits

This is when I started wearing my Travel Capsule, so if you were waiting to see how those outfits came together, this is where it begins! I didn’t even unpack my second suitcase after we moved hotels.

As I explained, I made a few changes for the purposes of that post—this navy stripe sweater, for example, is from last year and only available in limited sizes. I wanted everything I put in the capsule images to be in stock, so I swapped it for the LOFT collared stripe sweater instead. I had also planned to bring the Clare V. Ciao tee, but it didn’t arrive in time, so I brought my MOTHER Margarita Tee from last summer, which has since sold out.

I also adjusted the colors of a few pieces—the Seafolly coverup, Sea Level Cross Front Swimsuit, and Tommy Bahama sheath dress—to make a more cohesive color palette. And while it wasn’t pictured in the capsule, I brought along one extra swimsuit: the La Blanca Island Goddess One Piece.

You may also notice that I didn’t wear everything in the capsule. As it turns out, I didn’t need it all—live and learn! Okay, so anyway… here’s what I actually wore!

That evening, I changed back into jeans for our walk downtown to dinner. We ate at Kojo, a contemporary Asian fusion spot with a really cool vibe and incredible sushi.

Faherty sweater (S) (option) // PAIGE Anessa (29) (option) // Veronica Beard Via (8.5) // old rattan hoops // Anna Beck necklace

As much as we loved downtown Sarasota, I started to regret my decision to move hotels almost as soon as I arrived at The Modern. Alison, Deb, and I had stayed there last year when we came down to shoot spring outfits, and I loved it, so I wanted to go back and bring Paul. It’s a really cool hotel with a fun urban vibe, but after spending three days right on the beach, I missed the sound of the waves. Sitting on my balcony listening to traffic and construction just wasn’t cutting it.

So, I made arrangements to move back to Lido Beach Resort, and the next morning, we packed up to move! Knowing we probably wouldn’t be able to check into our room right away, I dressed for the day in that same cropped button-up with white shorts over a swimsuit and packed my beach tote with sunscreen and other essentials. That way, we could check our bags with the front deck and head straight to the pool. Funny enough, this top-and-shorts combo wasn’t something I had planned to wear together, but I ended up loving it.

stripe shirt (S) // Vineyard Vines shorts (8) // rag & bone Essential Straw Tote (option) // beek Sunbeam flip flops (8) // Jenny Bird hoops

Once we got into our new room later that afternoon, we freshened up for dinner. I wore the red-and-white striped sweater from my travel look with those cropped wide-leg jeans. I like this look better with sandals, but I decided to be practical and wear sneakers so I could walk comfortably to St. Armands Circle. The resort offers a free shuttle, but I felt like I needed the exercise—and it was a beautiful night!

red stripe sweater (M) // PAIGE Anessa (29) (option) // Paul Green sneakers (8) // similar bag // Tom Ford sunnies (option)

The next day was Paul’s birthday, and he wanted to visit the Ringling Circus Museum and Museum of Art, so I tagged along. We also wandered through the gardens and walked down to see Ca’ d’Zan, the Ringlings’ winter home, which was really cool. We didn’t pay the extra fee to go inside, but it was worth seeing from the outside. Sitting right on Sarasota Bay, the building is absolutely stunning. (It’s the one behind me in the photo below.)

For the day, I went with a sweater and shorts combo, one of my favorite pairings for mild weather, and finished the look with boat shoes for a classic-yet-trendy touch.

Faherty sweater (S) (option) // Vineyard Vines shorts (8) // Jeffrey Campbell boat shoes (8.5) // similar bag // Tom Ford sunnies (option) // Anna Beck necklace // Jenny Bird earrings

That night, we met up with some of Paul’s family for dinner at Columbia to celebrate his birthday. Funny enough, they happened to be in the area at the same time—a total coincidence!

I kept it simple and swapped my white shorts for white jeans. I also switched to sandals since my boat shoes were starting to give me a blister—they’re very comfortable, but they do take a little breaking in. And I brought my trench coat because it was quite windy, and I was glad I did—I definitely needed it, even though we took the resort shuttle to dinner and back.

Faherty sweater (S) (option) // similar trench // MOTHER Hustler (30) (option) // Veronica Beard Via (8.5) (option) // similar bag // Tom Ford sunnies (option) // Anna Beck necklace // Jenny Bird earrings

The next day was another pool day, and I wore my striped shirt and white shorts over my teal blue swimsuit again. We spent the whole day at the resort and had dinner at the Tiki Bar—nice and easy.

I did go up and change before eating diner that night because it got quite windy and chilly—I ran up and changed into a graphic tee, flare jeans, sneakers, and a sweatshirt. (I also wore that sweatshirt and tee with my Aritzia lounge pants a few times to work in the lobby in the mornings.)

MOTHER Margarita Tee (option) // Gap Factory hoodie (S) // Pistola Kinsley Flares (29) // Paul Green Hadley (8) (option)

On our last morning, we walked into downtown Sarasota for some exercise (and also because I wanted to pick up a sweatshirt to commemorate our trip). Along the way, we stumbled upon a fun mural, so of course, I had to stop for a picture.

Zella tank (S) // Vineyard Vines shorts (8) // On Cloud sneakers (9) // Celine sunnies (option)

Then it was back to the beach for our last day… which was actually the only day we spent on the beach! The pool is just so convenient, but with the ocean right there, I told Paul it would be a crime not to spend at least a little time by the water. It was the perfect sunny, warm, breezy day; and I took the opportunity to finish my book—Kristin Hannah’s Home Front.

Seafolly cover-up (M) // rag & bone Essential Straw Tote (option) // Celine sunnies (option) // Eric Javits sun hat (option)

And yes, Paul was actually with me on this trip! He joked that I had to post at least one picture together to prove to his work colleagues that he was really here, so we snapped this selfie on the beach.

Sea Level Cross Front Swimsuit (10) // Celine sunnies (option) // Eric Javits sun hat (option) // Jenny Bird earrings

For dinner on our last night, I went back to my cropped striped button-up and white ankle flare jeans. I took Paul to Crab & Fin, but unfortunately, it wasn’t as good as it was when I went with the girls. I’m not sure if it was just because it was a Monday, but the fish didn’t seem that fresh, and we felt rushed. I probably won’t go back again.

stripe button-up (S) // MOTHER Hustler (30) (option) // Veronica Beard Via (8.5) (option) // similar bag // Jenny Bird hoops // Anna Beck toggle necklace

And one more proof of life… While Paul was taking my picture, a kind gentleman walking by offered to snap one of us together. We gratefully accepted! I always feel awkward asking people to take our picture, but it’s so nice when someone offers.

The sunset was beautiful that night, so we sat on the beach for a bit before heading out for dinner.

Sunset on Lido Beach

The next morning, I threw on my new Sarasota sweatshirt and Pistola flares to go down to work in the lobby, and I ended up keeping it on and wearing it home. Fortunately, Paul was able to fit my trench coat into his suitcase because mine were at capacity! Next year, I should bring two medium-sized bags.

Sarasota sweatshirt // Pistola Kinsley Flares (29) // Paul Green Hadley (8) (option) // rag & bone tote (budget option)