Well Planned · Lookbook
Sam's Costa Rica Trip
May 8–15, 2027 · Liberia & Playa Potrero, Costa Rica · I'm Never Coming Home (7-10 outfits) package
Here's what we're recommending for Sam's trip so far:
- Beach Day is built around the Brixton straw hat and OluKai sandals you're already bringing — each tier gives you a different bikini + cover-up option.
- Birthday Dinner is built around your Free People Genevieve dress.
- Portrero Town Day is built with your Gigi Pip Capri hat and OluKai sandal.
- Your Travel Day centers around your black Lululemon leggings and taupe Sambas — each tier adds a different cozy layer for the flight.
- Pool Day has a fresh bikini and cover-up combo for lounging by the water.
- Casual Dinner is built around a relaxed linen dress and your Rainbow wedge.
- Historic/Cultural Tour Day is designed for a day of walking and sightseeing.
Every purchasable item below is currently verified in stock in your size (top/bottom S, shoe 7), in the pictured color, with a real product photo.
Look 1 · Beach Day at Playa Potrero
Effortless & Beachy
A good-quality bikini paired with a cute, comfortable cover-up — built around the straw hat and beach sandals you're already bringing.
Under Budget
Total $105.00
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Bikini Top
Offshore Top - Jet
$75.00Size S · in stock
A sage-green two-piece with good-quality Italian fabric.
View product — Offshore Top - Jet (opens in a new tab) Bottom
Wear your own bottom
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Cover-Up
Summer Oasis Beige Cover-Up Dress
$30.00Size S · in stock
A sheer cover up dress, perfect for a day at the beach.
View product — Summer Oasis Beige Cover-Up Dress (opens in a new tab) -
Accessory Bringing your own
Joanna Straw Hat — Honey
$0.00Size One size · you own this
View product — Joanna Straw Hat — Honey (opens in a new tab) -
Shoe Bringing your own
'Uiki Water-Friendly Beach Sandal — Lava Rock
$0.00Size 7 · you own this
View product — 'Uiki Water-Friendly Beach Sandal — Lava Rock (opens in a new tab)
On Budget
Total $108.94
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Bikini Top
Ruffle Trim Smocked Bikini Set
$56.95Size S · in stock
A ruffle trim set in white.
View product — Ruffle Trim Smocked Bikini Set (opens in a new tab) Bottom
Bottom included in set above
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Cover-Up
Janey Maxi Cover-Up Dress
$51.99Size S · in stock
A sheer breathable cover up for the beach.
View product — Janey Maxi Cover-Up Dress (opens in a new tab) -
Accessory Bringing your own
Joanna Straw Hat — Honey
$0.00Size One size · you own this
View product — Joanna Straw Hat — Honey (opens in a new tab) -
Shoe Bringing your own
'Uiki Water-Friendly Beach Sandal — Lava Rock
$0.00Size 7 · you own this
View product — 'Uiki Water-Friendly Beach Sandal — Lava Rock (opens in a new tab)
Splurge
Total $308.00
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Bikini Top
Tubular Top - Bronze
$110.00Size S · in stock
A strap free top.
View product — Tubular Top - Bronze (opens in a new tab) -
Bottom
Wear to Bottom - Deep End (Teal)
$100.00Size S · in stock
View product — Wear to Bottom - Deep End (Teal) (opens in a new tab) -
Cover-Up
Portia Skirt Set - Lone Lake
$98.00Size S
A sheer, cotton gauze maxi for layering.
View product — Portia Skirt Set - Lone Lake (opens in a new tab) -
Accessory Bringing your own
Joanna Straw Hat — Honey
$0.00Size One size · you own this
View product — Joanna Straw Hat — Honey (opens in a new tab) -
Shoe Bringing your own
'Uiki Water-Friendly Beach Sandal — Lava Rock
$0.00Size 7 · you own this
View product — 'Uiki Water-Friendly Beach Sandal — Lava Rock (opens in a new tab)
Look 2 · Birthday Dinner with Old Friends
Beachy & Special
Your own Genevieve dress does the heavy lifting — each tier adds finishing accessories.
Under Budget
Total $86.90
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Dress Bringing your own
Genevieve Midi Dress — Blue Blaze
$0.00Size S · you own this
View product — Genevieve Midi Dress — Blue Blaze (opens in a new tab) -
Shoe
Chocolate flats
$18.90Size 7
A brown shoe to compliment the earrings.
View product — Chocolate flats (opens in a new tab) -
Accessory
Gold Boho Hoops
$68.00Size One size · in stock
18k Gold classic hoops.
View product — Gold Boho Hoops (opens in a new tab) Accessory
Accessory — still open
On Budget
Total $116.80
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Dress Bringing your own
Genevieve Midi Dress — Blue Blaze
$0.00Size S · you own this
View product — Genevieve Midi Dress — Blue Blaze (opens in a new tab) -
Shoe
Black Flats
$18.90Size 7
A black shoe to compliment the jewerly.
View product — Black Flats (opens in a new tab) -
Accessory
Bezel Freshwater Pearl Earrings
$58.00Size One size · in stock
Pear earrings with gold accent.
View product — Bezel Freshwater Pearl Earrings (opens in a new tab) -
Accessory
Cagliari - Rattan Clutch
$39.90Size One Size · in stock
Black & Gold accents to complete the look.
View product — Cagliari - Rattan Clutch (opens in a new tab)
Splurge
Total $237.90
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Dress Bringing your own
Genevieve Midi Dress — Blue Blaze
$0.00Size S · you own this
View product — Genevieve Midi Dress — Blue Blaze (opens in a new tab) -
Shoe
Black Flats
$49.90Size 7
A black shoe with gold accent to tie into the earrings and clutch.
View product — Black Flats (opens in a new tab) -
Accessory
14K Gold Gemstone Tiny Huggie - Single
$88.00Size One size · in stock
Classy earrings to compliment your dinner look.
View product — 14K Gold Gemstone Tiny Huggie - Single (opens in a new tab) -
Accessory
Eloise Clutch - Black
$100.00Size One Size · in stock
View product — Eloise Clutch - Black (opens in a new tab)
Look 3 · Portrero Town Day
Casual & Exploring
Breezy dresses you can walk the whole town in, paired with the sandal and straw hat you're already bringing.
Under Budget
Total $74.99
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Dress
Maren Linen Dress
$74.99Size XS · in stock
Casual linen dress.
View product — Maren Linen Dress (opens in a new tab) -
Accessory Bringing your own
Capri Hat — Brown
$0.00Size One size · you own this
View product — Capri Hat — Brown (opens in a new tab) -
Shoe Bringing your own
Kipe'a 'Olu Sandal — Sahara
$0.00Size 7 · you own this
View product — Kipe'a 'Olu Sandal — Sahara (opens in a new tab)
On Budget
Total $118.00
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Dress
Lexi Rib Split Dress
$118.00Size XS · in stock
Linen dress — for town exploring.
View product — Lexi Rib Split Dress (opens in a new tab) -
Accessory Bringing your own
Capri Hat — Brown
$0.00Size One size · you own this
View product — Capri Hat — Brown (opens in a new tab) -
Shoe Bringing your own
Kipe'a 'Olu Sandal — Sahara
$0.00Size 7 · you own this
View product — Kipe'a 'Olu Sandal — Sahara (opens in a new tab)
Splurge
Total $138.00
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Dress
Romy Striped Linen Maxi Dress — Eclipse
$138.00Size XS · in stock
A linen blend, effortless maxi.
View product — Romy Striped Linen Maxi Dress — Eclipse (opens in a new tab) -
Accessory Bringing your own
Capri Hat — Brown
$0.00Size One size · you own this
View product — Capri Hat — Brown (opens in a new tab) -
Shoe Bringing your own
Kipe'a 'Olu Sandal — Sahara
$0.00Size 7 · you own this
View product — Kipe'a 'Olu Sandal — Sahara (opens in a new tab)
Look 4 · Travel Day (ND → Costa Rica)
Comfy & Easy
Your own black leggings and taupe Sambas do the work — each tier adds a cozy crewneck layer for the flight.
Under Budget
Total $61.00
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Layer
CloudComfort Crewneck Sweatshirt — Soft Ivory
$36.00Size S · in stock
An ultra-soft, cloud-like crewneck in a warm ivory — easy to throw on for a long travel day.
View product — CloudComfort Crewneck Sweatshirt — Soft Ivory (opens in a new tab) -
Bottom Bringing your own
Align High-Rise Pant 28″ — Black
$0.00Size S · you own this
View product — Align High-Rise Pant 28″ — Black (opens in a new tab) -
Top
Women's Super Flex High Neck Racerback Support Tank Top
$25.00Size S · in stock
A black layer for landing in Costa Rica.
View product — Women's Super Flex High Neck Racerback Support Tank Top (opens in a new tab) -
Shoe Bringing your own
Samba OG — Taupe Oxide
$0.00Size 7 · you own this
View product — Samba OG — Taupe Oxide (opens in a new tab)
On Budget
Total $112.99
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Layer
Inspire Layer - Doe
$48.00Size XS · in stock
Easy layer for leaving Utah.
View product — Inspire Layer - Doe (opens in a new tab) -
Bottom
Cotton Gauze Easy Joggers
$39.99Size S
Comfy balloon pants for travel.
View product — Cotton Gauze Easy Joggers (opens in a new tab) -
Top
Women's Super Flex High Neck Racerback Support Tank Top
$25.00Size S · in stock
A brown layer for landing in warmer weather.
View product — Women's Super Flex High Neck Racerback Support Tank Top (opens in a new tab) -
Shoe Bringing your own
Samba OG — Taupe Oxide
$0.00Size 7 · you own this
View product — Samba OG — Taupe Oxide (opens in a new tab)
Splurge
Total $166.00
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Layer
Halo Modern Crew — Pale Grey Heather
$98.00Size S · in stock
A cropped, DreamKnit-soft pullover — the splurge-tier layer, elevated but still built for comfort in transit.
View product — Halo Modern Crew — Pale Grey Heather (opens in a new tab) -
Bottom Bringing your own
Align High-Rise Pant 28″ — Black
$0.00Size S · you own this
View product — Align High-Rise Pant 28″ — Black (opens in a new tab) -
Top
Pose Plyo Tank - French Roast
$68.00Size S · in stock
View product — Pose Plyo Tank - French Roast (opens in a new tab) -
Shoe Bringing your own
Samba OG — Taupe Oxide
$0.00Size 7 · you own this
View product — Samba OG — Taupe Oxide (opens in a new tab)
Look 5 · Pool Day
Easy & Poolside
A good-quality bikini paired with a breezy crochet cover-up — simple and effortless for lounging by the water.
Under Budget
Total $120.00
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Bikini Top
Italian V-Neck Bikini Top — Deep Navy
$25.00Size S · in stock
A simple, good-quality Italian-fabric two-piece in deep navy — easy and effortless for the pool.
View product — Italian V-Neck Bikini Top — Deep Navy (opens in a new tab) -
Bottom
Italian High-Rise Bikini Bottom
$25.00Size S · in stock
Completes the set.
View product — Italian High-Rise Bikini Bottom (opens in a new tab) -
Cover-Up
Windward Tee Dress — Black
$70.00Size XS · in stock
A sheer maxi cover-up in black — simple, effortless, and easy to throw over the bikini.
View product — Windward Tee Dress — Black (opens in a new tab)
On Budget
Total $190.00
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Bikini Top
Elba Compression Top
$78.00Size S · in stock
Leopard print bikini top.
View product — Elba Compression Top (opens in a new tab) -
Bottom
Mae Compression Bottom
$68.00Size S · in stock
Matching bottom for a put together look.
View product — Mae Compression Bottom (opens in a new tab) -
Cover-Up
Breathtaking White Maxi Dress - White
$44.00Size S · in stock
The maxi cover-up in white for effortless layering.
View product — Breathtaking White Maxi Dress - White (opens in a new tab)
Splurge
Total $289.00
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Swimsuit
La Crosse Top - Cold Brew
$110.00Size S · in stock
Brown bikini top with cross back.
View product — La Crosse Top - Cold Brew (opens in a new tab) -
Bottom
Wear To Bottom - Cold Brew / Stormy / Sandal
$115.00Size S · in stock
Matching bottom for a put together look.
View product — Wear To Bottom - Cold Brew / Stormy / Sandal (opens in a new tab) -
Cover-Up
Dylan Gauze Sarong
$64.00Size One Size · in stock
The sarong cover-up in black for effortless layering.
View product — Dylan Gauze Sarong (opens in a new tab)
Look 6 · Casual Dinner
Relaxed & Simple
A relaxed linen dress paired with your own Rainbow wedge — simple and effortless for an easy dinner out.
Under Budget
Total $48.99
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Dress
Ottilie Cotton Dress - Green
$48.99Size S · in stock
A relaxed cotton dress in green — simple, effortless, easy for a casual dinner out.
View product — Ottilie Cotton Dress - Green (opens in a new tab) -
Shoe Bringing your own
Madison Six Layer Wedge — Premier Black
$0.00Size You own this Also in Look 2
View product — Madison Six Layer Wedge — Premier Black (opens in a new tab)
On Budget
Total $118.00
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Dress Also in Look 3
Lexi Rib Split Dress - Chocolate
$118.00Size XS · in stock
A fun cotton dress for a casual dinner.
View product — Lexi Rib Split Dress - Chocolate (opens in a new tab) -
Shoe Bringing your own
Madison Six Layer Wedge — Premier Black
$0.00Size You own this Also in Look 2
View product — Madison Six Layer Wedge — Premier Black (opens in a new tab)
Splurge
Total $138.00
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Dress
Bianca Maxi Dress
$138.00Size XS · in stock
A flowy, viscose maxi for evening plans.
View product — Bianca Maxi Dress (opens in a new tab) -
Shoe Bringing your own
Madison Six Layer Wedge — Premier Black
$0.00Size You own this Also in Look 2
View product — Madison Six Layer Wedge — Premier Black (opens in a new tab)
Look 7 · Historical Tour / Sightseeing Day
Elevated Casual
Under Budget
Total $142.00
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Top
Lexi Rib Sun-In Tank - White
$54.00Size S
View product — Lexi Rib Sun-In Tank - White (opens in a new tab) -
Bottom
Allison Hemp Short - Cream/Navy Stripe
$88.00Size XS
View product — Allison Hemp Short - Cream/Navy Stripe (opens in a new tab) Bag
No bag for this look - staying under budget
On Budget
Total $254.00
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Top
Lexi Rib Sun-In Tank - White
$54.00Size XS
View product — Lexi Rib Sun-In Tank - White (opens in a new tab) -
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Bag
Cass Phone Crossbody - Black
$128.00Size One Size · in stock
View product — Cass Phone Crossbody - Black (opens in a new tab)
Splurge
Total $292.95
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Bottom
Lydia Bubble Skirt - Black
$29.95Size M
View product — Lydia Bubble Skirt - Black (opens in a new tab) -
Bag
Sable Crossbody - Truffle
$195.00Size Size
View product — Sable Crossbody - Truffle (opens in a new tab)
