In much the same way that getting ready for a night out is often more fun than actually going out, I find packing for a trip to be just as fun as the travel itself. Okay, maybe not just as fun, but I really do love the process. From rediscovering favorites in my own wardrobe to investing in a few new pieces to round out my vacation wardrobe, to attempting to stuff it all into my packing cubes (I like the compression ones), packing challenges me to plan out looks in advance and really make the most of my options.

For this particular trip—a return to my favorite villa in Jamaica for a week of swimming, lounging and cheers-ing Aperol spritzes—the vibes were elevated resortwear, comfy-but-cute linens, and swimsuits that are nice enough to don sans-cover-up. (Not to toot my own horn, but I think I nailed it.)

When it comes to purchasing new items for a trip, I do my best to not buy things I’ll only wear for this one occasion (I turned to rental apps and subscriptions like Vivrelle for those need-it-for-one-night picks), so the majority of this list will see me through the entirety of summer 2025 to come. 

Read on for the $10 sarong I threw on with everything, the swimsuits I recommend for style and support, and of course, a few statement pieces to wow everyone on the beach. 

• Must-Have Matching Set: Old Navy High-Waisted Crinkle Gauze Wide-Leg Pants, $20 (Originally $40); oldnavy.gap.com and Crinkle Gauze Button-Down Shirt, $20 (Originally $37); oldnavy.gap.com
• Swimsuit for Larger Chests: Robin Piccone Ava Knit One-Piece Swimsuit, $178; nordstrom.com
• Worth the Splurge: Baobab Nia Maxi Dress, $300; baobabstore.com
•  Vitamin A Skylar Bikini Top, $115; vitaminaswim.com and Lolita Bikini Bottom, $100; vitaminaswim.com
• Bought Multiple Pairs: Ray-Ban RB4441D Bio-Based Sunglasses, $151; amazon.com and sunglasshut.com
• My Favorite Sarong: Ekouaer Short Sarong, $10; amazon.com
• Abercrombie Curve Love Wide Strap Bikini Top, $55; abercrombie.com and Mid Rise High-Leg Moderate Bottom, $40; abercrombie.com
• Comfy Pool-Side Essential: Free People Free-est Roberta Sweater Set, $128; freepeople.com
• 2-in-1 Swimsuit: Jessie Zhao Red Blossom Reversible One-Piece Swimsuit, $159; nordstrom.com
• Anthropologie Daily Practice Full Twist Pants, $88; anthropolgie.com
• $16 Bikini: Cider Floral Texture Heart Link Criss Cross Bikini, $16; shopcider.com
• Farm Rio x Anthropologie Fish-Print Midi Skirt, $150; anthropologie.com
• Lack of Color Seashells Cowboy Hat, $119; amazon.com
• Farm Rio Red Garden Lenzing Ecovero Euroflax Midi Dress, $360; farmrio.com
• Robin Piccone Lyra Stripe Cap Sleeve Bikini Top, $89 (Originally $118); nordstrom.com and High Waist Bikini Bottoms, $67 (Originally $86); nordstrom.com

Old Navy High-Waisted Crinkle Gauze Wide-Leg Pants

Old Navy Crinkle Gauze Button-Down Shirt

Old Navy really nails their summery matching sets, and this season’s lineup includes a stripey combination I couldn’t pass up. I always recommend picking up solids like black, white or navy, but once you’ve got your basics down, why not have some fun with the High-Waisted Crinkle Gauze Wide-Leg Pants and Crinkle Gauze Button-Down Shirt in red stripes? For me, this was an instant add-to-cart.

Robin Piccone Ava Knit One-Piece Swimsuit

Robin Piccone is my go-to swimsuit recommendation for gals with larger chests that want coverage that isn’t too dowdy. I ended up snagging multiple swimsuits during a shopping trip at Nordstrom, and they’re the perfect combination of practical and special. The Ava Knit One-Piece Swimsuit is the kind of piece that I believe every woman needs in her one-piece wardrobe. It’s modest and timeless, but the tie-front detail adds a little spice. I styled mine with a Lack of Color hat and a sarong.

Baobab Nia Maxi Dress

I needed one standout nighttime look for a fancy dinner during my trip, and I knew Baobab would have the appropriate pieces to make me feel like a mermaid—especially when styled with a fresh tan and a drink in hand. I landed on the Nia Maxi Dress; its flattering ruching andmetallic sheen looked amazing in photos.

Vitamin A Skylar Top

Vitamin A Lolita Bottom

Vitamin A swimwear is definitely on my radar this season, mainly because it has an entire section of their website devoted to supportive swim—music to my ears (err, chest)! I love the ring detail and the vibey pattern on the Skylar Top and Lolita Bottom. Might’ve also copped the matching Samara Sarong, because I can’t help myself.

Ray-Ban RB4441D BIO-BASED Sunglasses

I took a trip to SoHo to try on glasses at Sunglass Hut in search of the perfect pair for vacation and beyond, and I landed on a new-to-me style of Ray-Bans so good, I ended up getting them in two different colors. The RB4441D Bio-Based sunnies strike the perfect balance between retro model chic and IG model cool, and I had to pick up the polished white in addition to matte opal brown. The latter is an especially good option for anyone who wants an alternative to classic black, but isn’t a fan of a tortoiseshell frame.  

Ekouaer Short Sarong

FYI, this is my favorite sarong, and it’s under $10 bucks on Amazon. The Ekouaer Short Sarong is sheer and comes in thirty-seven colors, but I also make sure I have classic black on hand to throw over my swimsuits.

Abercrombie Curve Love Wide Strap Underwire Bikini Top

Abercrombie Mid Rise High-Leg Moderate Bottom

My sister is a massive fan of Abercrombie swimwear, so she encouraged me to order a few styles, and when I saw this cutesy cherry printed suit, I was sold. The Curve Love Wide Strap Underwire Bikini Top gives ample support, and while I opted for the Mid Rise High-Leg Moderate Bottom, they also do the print in a string style, should you want to get a bit cheeky. 

Free People Free-est Roberta Sweater Set

When I saw the free-est Roberta Sweater Set at Free People, my summer-loving heart genuinely skipped a beat. This crop top and drawstring pant combo are done in a towel-like terry material, perfect for throwing on over a swimsuit or wearing to lounge poolside. I picked up the ivory combo colorway, but I also snagged the yellow and brown versions for my sisters as a pre-vacation treat.

Jessie Zhao Red Blossom Reversible One-Piece Swimsuit

Jessie Zhao is a brand I fell in love with a few years back because of its unique reversible swimsuits, so I picked up the Red Blossom Reversible One-Piece Swimsuit, which boasts a floral print on one side and a more tropical design on the other. The best part about these suits has to be the straps, which are extra-long and meant to be tied as bows to guarantee a perfect fit and a cute coquette finish.

Anthropologie Daily Practice Full Twist Pants

I knew I’d be doing yoga on the trip, but given Jamaica’s notorious humidity, I cringed at the thought of yanking on skin-tight leggings for a sweaty workout. In search of cute, breathable gym wear, I realized Daily Practice dropped more colors of my favorite track pants, the Full Twist Pants. I love the little bow details on the sides, and the vibrant red was a no-brainer.

Cider Floral Texture Heart Link Criss Cross Bikini

I can’t help but feel like swimsuits are getting more expensive by the minute, so I also turned to Cider to find some affordable options that felt a bit more trend-forward than my usual selections. You can’t tell me the Floral Texture Heart Link Criss Cross Bikini doesn’t give you Sabrina Carpenter vibes. 

Farm Rio x Anthropologie Fish-Print Midi Skirt

Reader, do not sleep on beachwear that can double as real-world attire. This Farm Rio x Anthropologie Fish-Print Midi Skirt is the perfect throw-on sarong for the pool, but it also has a hidden button closure that makes it secure enough to wear as a skirt to dinner, too. Packing pieces I can style multiple ways is a life-saver, especially when my suitcase inevitably nears the dreaded weight limit.

Lack of Color Seashells Cowboy Hat

I’m big on sun protection, so a few cute hats are always worth cramming in my suitcase. This season, I opted for this Lack of Color Seashells Cowboy Hat in addition to my usual floppy styles. It’s a little more playful, and still did a great job of keeping my face shielded from the sun.

Farm Rio Red Garden Lenzing Ecovero Euroflax Midi Dress

Farm Rio is my forever go-to for special summer dresses, and the Red Garden Lenzing Ecovero Euroflax Midi Dress was a no-brainer. The 3D flower detail at the bust is beautiful and unique—and as a plus, I didn’t even need to wear a bra. Major vacation win.

Robin Piccone Lyra Stripe Cap Sleeve Bikini Top

Robin Piccone High Waist Bikini Bottoms

Also from Robin Piccone, I grabbed the Lyra Stripe Cap Sleeve Bikini Top and coordinating High Waist Bikini Bottoms. The short-sleeved silhouette is perfect for when my shoulders inevitably burn after too much time in the sun, and the crochet trompe l’oeil print is a lot more practical to pack than the real thing.