Well Planned · Lookbook
Jen's Montego Bay, Jamaica Trip
Nov 23–28, 2026 · Montego Bay, Jamaica · Personalized Package
Here's what we're recommending for Jen's trip:
- Four looks — a pool day, a beach day, an anniversary dinner, and a travel day — each with an Under Budget, On Budget, and Splurge option so you can choose the mix that works best.
Every item below is currently verified in stock in your size (S), in the pictured color, with a real product photo.
Look 1 · Pool Day
Classic & Easy
Wear your own black bikini, or swap in a navy or polka-dot bikini — each paired with a crochet or gauze cover-up and a packable fedora. Pair with your own brown Rainbow wedges and Quay cat-eye sunglasses.
Under Budget
Total $53.99
Top
Wear your own black bikini — top
Bottom
Wear your own black bikini — bottom
-
Cover-Up
Crochet Scoop Back Swim Cover-Up Dress — Multi
$30.00Size S · in stock
An open-back crochet cover-up in a multi stripe that pairs easily with your own black bikini.
View product — Crochet Scoop Back Swim Cover-Up Dress — Multi (opens in a new tab) -
Accessory
Fedora Sun Hat — Beige
$23.99Size M · in stock
A wide-brim, UV-protective fedora that packs flat — worn across all three tiers of this look.
View product — Fedora Sun Hat — Beige (opens in a new tab)
On Budget
Total $91.99
-
Top
Smocked Bralette Bikini Top — Navy Blue
$18.00Size S · in stock
A smocked bralette top in classic navy for a colour swap from your own black bikini.
View product — Smocked Bralette Bikini Top — Navy Blue (opens in a new tab) -
Bottom
Solid Tricot Low-Rise Bikini Bottom — Navy Blue
$15.00Size S · in stock
Matching navy bottom, low-rise with medium coverage.
View product — Solid Tricot Low-Rise Bikini Bottom — Navy Blue (opens in a new tab) -
Cover-Up
Crochet Square Neck Midi Cover-Up Dress — Cream
$35.00Size S · in stock
A longer square-neck crochet midi for more coverage between the pool and lunch.
View product — Crochet Square Neck Midi Cover-Up Dress — Cream (opens in a new tab) -
Accessory Same as Under
Fedora Sun Hat — Beige
$23.99Size M · in stock
View product — Fedora Sun Hat — Beige (opens in a new tab)
Splurge
Total $100.99
-
Top
Balconette Underwire Polka Dot Top — Cream
$30.00Size S · in stock
An underwire balconette top in a graphic polka dot for extra structure and support.
View product — Balconette Underwire Polka Dot Top — Cream (opens in a new tab) -
Bottom
Reversible Polka Dot High Waist Cheeky Bottom — White/Black
$22.00Size S · in stock
A reversible high-waist bottom — wear the polka dot side or flip to solid, cheeky coverage.
View product — Reversible Polka Dot High Waist Cheeky Bottom — White/Black (opens in a new tab) -
Cover-Up
Gauze Swim Cover-Up Shirtdress — Black
$25.00Size S · in stock
A breezy gauze shirtdress cover-up in black for a dressier splurge look.
View product — Gauze Swim Cover-Up Shirtdress — Black (opens in a new tab) -
Accessory Same as Under
Fedora Sun Hat — Beige
$23.99Size M · in stock
View product — Fedora Sun Hat — Beige (opens in a new tab)
Look 2 · Beach Day
Sand & Sun
Same bikini as Pool Day, styled as a beach look, with a shorts + top set for walking to lunch or the market.
Under Budget
Total $36.99
-
Bottom
Linen 2 piece set
$36.99Size S · in stock
Cute linen set that can be worn to beach, pool or dinner!
View product — Linen 2 piece set (opens in a new tab) Shoe
Wear your own shoe
On Budget
Total $53.94
-
Set
Summer 2 piece set
$35.99Size 00-0
Another cute cover up --> happy hour outfit!
View product — Summer 2 piece set (opens in a new tab) -
Splurge
Total $150.98
-
Dress
Floral Cover Up
$50.99Size XS · in stock
Beach --> Happy Hour
View product — Floral Cover Up (opens in a new tab) -
Shoe
Women's Bay Flat Sandal
$99.99Size 7.5 · in stock
View product — Women's Bay Flat Sandal (opens in a new tab)
From your closet: Quay cat-eye sunglasses, packable sun hat (same as Look 1).
Look 3 · Anniversary Dinner
Beachy & Bright
A fun, beachy dress with room for a wedge, or the black flats from Look 2.
Under Budget
Total $37.99
-
Dress
Summer Maxi
$37.99Size S · in stock
A flowy floral maxi with room for a wedge sandal.
View product — Summer Maxi (opens in a new tab)
On Budget
Total $45.99
-
Dress
Summer Spaghetti Strap
$45.99Size S · in stock
A vibrant, beach-getaway maxi for a fun dinner look.
View product — Summer Spaghetti Strap (opens in a new tab)
Splurge
Total $125.00
-
Dress
Carmen Smocked Dress
$125.00Size XS · in stock
A statement tropical-print maxi from a beloved resortwear designer.
View product — Carmen Smocked Dress (opens in a new tab)
Look 4 · Travel Day
North Dakota to Jamaica
Comfy enough to leave North Dakota in, arriving ready for Jamaica in November — a soft jogger set that layers down easily once you land.
Under Budget
Total $56.97
-
Set
Striped Set
$39.98Size S · in stock
Soft, relaxed joggers comfortable for a long travel day.
View product — Striped Set (opens in a new tab) -
Layer
Black
$16.99Size S · in stock
A soft layering top, warm enough for North Dakota and easy to shed on arrival.
View product — Black (opens in a new tab)
On Budget
Total $127.97
-
Bottom
Daily Legging
$98.00Size S · in stock
A step up in fabric quality for a full travel day.
View product — Daily Legging (opens in a new tab) -
Layer
Forever Fleece 1/2 Zip Hoodie — Black
$29.97Size S · in stock
A cozy half-zip fleece — warm for departure, easy to tie around your waist later.
View product — Forever Fleece 1/2 Zip Hoodie — Black (opens in a new tab)
Splurge
Total $226.00
-
Bottom
Align Foldover Relaxed Jogger
$128.00Size 4 · in stock
Buttery-soft premium travel jogger.
View product — Align Foldover Relaxed Jogger (opens in a new tab) -
Layer
Mountain High Half-zip Fleece
$98.00Size S · in stock
A fleece layer warm for departure, easy to tie around your waist later.
View product — Mountain High Half-zip Fleece (opens in a new tab)
