PAIGE Anessa Twisted (30) // Splendid Faye V-Neck (L) // similar belt // Splendid Lounge Jacket c/o (M) // On Cloud 6 (9) // Quince Expandable Carry-On & Transit Quilted Duffle // Marlyn Schiff Bayla Necklace c/o // Quince hoops

What This Trip Looks Like

Before we get into the packing list, I think it helps to know what this trip actually looks like. Paul and I are spending a week with family in an Airbnb, bookended by two resort stays. We originally planned three nights on each end, but both resorts were offering a fourth night free, so we figured, why not? That brings us to a total of 16 days away, including travel days.

The weather in Philadelphia this time of year is so unpredictable, so we’ve started extending this trip a little longer every year. It’s nice to get away for a while and enjoy Florida’s warm, sunny weather.

Most days are spent at the pool or beach, followed by dinner out in the evenings, so I don’t need a lot of casual daytime outfits—but I still like to be prepared for whatever comes up.

What I Packed: The Core Pieces

Here’s everything I packed for the trip (clothing only). It looks like a lot, but for two weeks, I’ll definitely be wearing everything here at least twice.

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Here’s how it breaks down:

Shorts

I brought three pairs of shorts, which was probably overkill. So far I’ve only worn the two non-denim pairs, but with another week left, I may still be glad I packed them all. The denim shorts can always double as a swim cover-up.

Denim

I traveled in wide-leg blue jeans and packed slim straight white ankle jeans for dinners and cooler days—both have definitely been worth bringing, especially since evenings here have been mild.

Dresses

Tommy Bahama Beleza Shift Dress (M) // Sam Edelman Camille (8) // J.Crew Portofino Clutch // Isla Gold Bead Necklace & Astra Pavé Paperclip Necklace c/o Thatch // Rogan Pearl Earrings c/o Lizzie Fortunato // Triple Row Bracelet

I brought three dresses and have been rotating them for dinners, which has worked out perfectly. One also doubles as a swim cover-up.

Tops

I brought a mix of sleeveless and short-sleeve tops, including a white t-shirt and a neutral striped tank, which work as base layers or can be worn on their own with accessories. I also packed a graphic tee, a more elevated sweater tank to dress up my white jeans, and a few additional tops that work with both shorts and denim.

Altogether, I brought seven tops, which feels a bit excessive… but this is always the hardest category for me to narrow down. They take up so little space, it’s easy to justify “just one more.”

Layers

I only brought one true jacket, the Splendid Lounge Denim Jacket in Moonstone, which I wore on the plane. I haven’t needed it here in Florida yet, but it may still come in handy.

At the last minute, I swapped my denim jacket for a short-sleeve version, and that was the right call. It works more as an outfit piece than a true layer, so I’ve actually been able to wear it.

MVP Piece

Frank & Eileen Jackie T-shirt Cardigan c/o (M) // PAIGE Olivia (30) // Dolce Vita Dom Sandals (8) // Bryan Anthonys Sea Seeker & You Are My Sunshine Necklace c/o (20% off with JOLYNNE20) // YSL sunnies

My Frank & Eileen Jackie T-shirt Cardigan has been the unexpected MVP of this travel capsule. It’s the only lightweight long-sleeve layer I brought, and I’ve worn it multiple ways—with shorts to dinner, thrown on over my pajamas in the mornings, and if we get any cooler evenings, it will be perfect with my wide-leg jeans.

What I Miss

The one thing I wish I had is my J.Crew beach sweater. I pulled it out it at the last minute, thinking the t-shirt cardigan would be enough, and technically it has been, but I do miss having a soft pullover.

Everything Else I Packed

Here’s what I packed to round out the outfits—shoes, bags, accessories, swimwear, loungewear, and everything else!

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Shoes

I usually start with shoes when I’m building a packing list since they take up the most space and anchor each outfit.

I only brought one pair of sneakers this time to save room, so they had to be my athletic pair. I chose my On Cloud slip-ons in the Pearl/White.

From there, I added:

• gold flat strappy sandals (easy to dress up or down)
• molded footbed walking sandals (my most-worn pair so far)
• TKEES flip flops (for the pool and beach, and ultra-casual looks)
• raffia kitten heel slides (for dressier looks)
• brown thong sandals with stone details (for fun!)

So yes… shoes were probably my overage category—but everything fit!

Bags & Accessories

Madewell Rib Vest Tank (M) // PAIGE Anessa Twisted (30) // Dolce Vita Dom Sandals (8) // Bryan Anthonys Sea Seeker & You Are My Sunshine Necklace c/o (20% off with JOLYNNE20) // Jenni Bird Florence Earrings

I probably overdid it here, too, but it’s hard to know what you’ll need until you’re in it. I see my bags as an extension of my outfit—they help add variety, especially when I’m re-wearing pieces.

At the last minute, I slipped my Clare V. woven leather belt bag into my personal bag (it lays flat, so it’s easy to pack) because I realized I didn’t have a crossbody—and I’m so glad I did. I’ve used it a ton, especially when walking longer distances to dinner or heading out for a walk.

I also brought a raffia and leather shoulder bag (similar) for everyday, a straw clutch for dressier dinners (and to tuck into my beach tote to hold my phone and other essentials), and a straw beach tote (similar) that packs flat in my suitcase.

If this were a shorter trip, I would have eliminated the shoulder bag, but for two weeks, it’s been nice to have options.

Swim + Cover-Ups

crochet swimsuit cover-up (M) // TKEES square toe flip flops c/o (8) // Talbots swimsuit (10) // YSL sunnies // Quince globe hoops // similar straw tote

I packed four swimsuits for this trip. Two or three would have been enough, but I like having the variety.

I only brought one official cover-up, but I’ve also been using a dress or denim shorts and a tank, which has worked just as well and helps stretch my vacation capsule wardrobe.

I also packed my straw hat (turned upside down in my suitcase and filled with smaller items—a good packing trick!).

Activewear & Loungewear

Athleta Brooklyn Heights Cargo Pants (6) // Getaway Linen Blend Muscle Tank (M) // TKEES square toe flip flops c/o (8)

I threw in my Athleta Brooklyn Heights Cargo Pants and Getaway Linen Blend Muscle Tank at the last minute, and I’m really glad I did because they’ve been perfect for slow mornings. My Splendid SunSoft set has also worked well as a backup lounge/pajama option.

For workouts, I brought one extra tank and a pair of Vuori shorts, which has been more than enough.

And I only packed one pair of pajamas, knowing we’d have laundry, and that’s been plenty.

Accessories

I also brought a neutral belt (wore it on the plane) and a variety of jewelry to add interest to my simple looks. I basically filled up this travel jewelry case with bracelets, necklaces, and earrings—I figured, if I’m going to bring it, I might as well fill it!

I didn’t link everything below, but I included the highlights—at least the pieces I’ve worn so far.

What I’d Do Differently Next Time

Honestly, there isn’t much I would do differently, which tells me I’m getting pretty good at this! It really does take practice, though—the more I travel, the better I get at planning and knowing what I actually need and what I can skip.

If I had to offer advice for anyone packing for a two-week warm-weather trip (assuming you have access to laundry), here’s what I’d say:

• I could have packed fewer casual daytime outfits (two pairs of shorts and about five short-sleeve or sleeveless tops would have been plenty)
• Two to three swimsuits is enough
• Don’t skip a cozy layer—my Frank & Eileen t-shirt cardigan has worked out, but a lightweight sweater or sweatshirt would be nice to have
• I could have cut at least one pair of shoes (probably the brown embellished thong sandals) and one bag (the raffia shoulder bag or straw clutch)

Shop My Travel Capsule

I rounded up everything here in one easy spot. I’ll share a full roundup of what I actually wore when I get home, but hopefully this gives you a helpful starting point if you’re planning a similar trip!