Vacation Looks
Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.
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Vacation Dresses & Outfits for Effortless Getaways
Pack light and look luxe in vacay dresses and vacation outfits designed for sun-soaked escapes. Whether you’re poolside at a beach resort or exploring cobblestone streets, Windsor’s resortwear blends breezy fabrics, relaxed silhouettes, and bold prints for travel outfits you’ll want to wear on repeat.
Easy, Packable Styles
Slip into breezy maxi dresses in tropical prints or neutral tones—white, ivory, and tan—for instant cruisewear elegance. Chic rompers and vacay outfits like matching top-and-bottom sets in airy cotton or linen make packing a breeze and styling stress-free.
Day-to-Night Versatility
Transition from sunrise yoga to sunset cocktails in flowy sundresses or relaxed separates. Mix and match colorful vacation-ready separates—think high-waist shorts with off-shoulder tops—or choose effortless travel outfits in knit jumpsuits and wrap skirts that go anywhere.
Resort & Beach Essentials
Complete your look with stylish bikinis under sheer cover-up dresses or mesh tunics. Add slide sandals, statement sunglasses, and a woven tote for poolside chic. From beach days to rooftop lounges, these vacay dresses keep you feeling confident and carefree.
Ready to jet off in style? Explore Windsor’s full collection of vacation dresses and outfits online, in-app, or at your nearest Windsor store.
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Stay Wild Bikini Top
Stay wild and be the fiercest one at the beach! This bikini top's leopard print detailing will have your whole squad talking! Pair with the matching bikini bottoms for the most purrfect look.
Shop Matching Bottoms: Stay Wild Bikini Bottoms
Fit & Features
- Halter tie straps
- Triangle cups
- Tie back straps
- Leopard print detailing on the straps
- Includes removable padding
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0329
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Clear Obsession Open Wedges
We have a clear obsession for clear shoes, and these wedges are everything!
- Open pointed toe
- Double clear bands
- Open back
- Low wedge
- Patent design
Style Number/Barcode: 07406-0048
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Baguette Rhinestone Mini Hoop Earrings
Change up your look when you swap our your everyday hoops for something with a little more sparkle!
- Mini hoop earrings
- Baguette rhinestone detailing
- Omega closures
Style Number/Barcode: 07001-0304
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stack Star Resin Bangle Bracelet
The MVP of your arm candy lineup. This resin bangle brings bold, polished vibes—wear it solo for a clean statement or stack it high for instant drama.
Fit & Features
- Smooth resin material
- Classic bangle silhouette
- Solid structured fit
- Lightweight and comfortable
Style Number/Barcode: 07003-000114
Category Name: Vacation Looks
Price: $11.90
Availability: Out of Stock
Product Badge:- Ships Free
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Don't Call Me Sherpa Pj Top
Once the pj's are on don't bother calling because I'm in the for night friends! Don't forget to pick up the matching cozy pj shorts for an ultimate night in 'fit!
Shop Matching Bottoms: Don't Call Me Sherpa Pj Shorts
Fit & Features
- Crew neckline
- Long sleeves
- Cropped hemline
- Sherpa
- Moderate stretch
Style Number/Barcode: 07103-0054
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pj Party Cozy Sherpa Crop Top
Pj party of one please! This cozy 'fit is a must have for a solo movie marathon, sleep overs with the gals, or even a cuddle party with bae! Don't forget to pick up the matching bottoms!
Shop Matching Bottoms: Pj Party Cozy Sherpa Joggers
Fit & Features
- Crew neckline
- Long sleeves
- Cropped hemline
- Fuzzy soft sherpa
- Knit lining
- Minimal stretch
Style Number/Barcode: 07103-0103
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pj Party Cozy Sherpa Joggers
Pj party of one please! This cozy 'fit is a must have for a solo movie marathon, sleep overs with the gals, or even a cuddle party with bae! Don't forget to pick up the matching cropped top!
Shop Matching Top: Pj Party Cozy Sherpa Crop Top
Fit & Features
- High waist fit
- Banded ankles
- Fuzzy soft sherpa
- Knit lining
- Minimal stretch
Style Number/Barcode: 07103-0152
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bright & Bold Color Block Triangle Swim Top
Make a bright & bold entrance in this striking bikini top! Don't forget to pick up the matching swim bottoms to complete the look!
Shop Matching Bottoms: Bright & Bold Color Block Swim Bottoms
- Tank-Style Straps
- V Neckline
- Triangle-Styled Bralette I Removable Padding
- Moderate Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0325
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bright & Bold Color Block Swim Bottoms
Make a bright & bold entrance in these striking swim bottoms! Don't forget to pick up the matching swim top to complete the look!
Shop Matching Top: Bright & Bold Color Block Triangle Swim Top
- Mid-Rise Waist
- Contrasting At The Waist & Leg Openings
- High Cut Design
- Moderate Coverage
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0478
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunkissed Tie Front One Piece Swimsuit
Get sunkissed in all the right places when you slip into a sexy one piece swimsuit!
Fit & Features
- One piece
- Tie-front
- Cut-out detailing
- High leg design
- Lined
- Moderate stretch
- No padding included
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0129
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Vacation Mode One Piece Swimsuit
Get ready to go full blown vacation mode in this perfectly dusty blush one piece cut out swimsuit that is flattering in all the right places!
Fit & Features
- One piece
- Adjustable spaghetti straps
- Tie front detailing | Cut out center
- Hook closure
- Cheeky fit | Moderate stretch
- High rise sides
- Fully lined | Not padded
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0135
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Better At The Beach Bikini Bottoms
As we all know, life is better at the beach. Live your best life in a new bikini that has you ready to soak up the sun in the hottest way bb! Don't forget to pick up the matching top!
Shop Matching Top: Better At The Beach Bikini Top
Fit & Features:
- Micro bikini bottoms
- Ribbed fabrication
- Fully lined
- Stretchy string straps
- Cheeky coverage
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0479
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Better At The Beach Bikini Top
As we all know, life is better at the beach. Live your best life in a new bikini that has you ready to soak up the sun in the hottest way bb! Don't forget to pick up the matching bottoms!
Shop Matching Bottoms: Better At The Beach Bikini Bottoms
Fit & Features:
- Micro bikini top
- Ribbed fabrication
- Fully lined
- Stretch string straps
- No padding
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0327
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bring It Back Beaded Bracelet Set
Beaded bracelets are making a come back, and this set is the perfect neutral to compliment any and every look!
- Set of six bracelets
- Elastic with stretch
- Variety of beading
Style Number/Barcode: 07003-0071
Category Name: Vacation Looks
Price: $11.00 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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I Heart You Chain Locket Necklace
Put a little picture of the one you heart the most! We are thinking your pet wins most loved! How cute would your pup or kittens pic look in there right?!
- Heart locket necklace
- Chain link design
- Locket opens & snaps closed
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-0286
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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All Eyes On You One Swimsuit
All eyes will be on you babe in this sexy one piece!
Fit & Features
- Adjustable spaghetti straps that lead to a back horizontal strap
- Low back
- V neckline
- Dual front cut outs with lattice detailing
- Cheeky bottom
- No padding included
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0149
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Off The Shoulder Strappy Swimsuit
Oh so stylish and strappy, this off the shoulder one piece is majorly on trend.
Fit & Features
- Off the shoulder neckline | Short sleeves
- Square neckline | No padding
- Center front cut out with lattice detail
- High cut sides with strappy detailing
- Cheeky bottom
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0150
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bold Accents Resin Bangle Bracelet
A bold little accent that does all the talking. This resin bangle brings that polished-but-playful vibe—perfect for stacking or rocking solo.
Fit & Features
- Smooth resin material
- Classic bangle silhouette
- Solid structured fit
- Lightweight and comfortable
Style Number/Barcode: 07003-000112
Category Name: Vacation Looks
Price: $3.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Gemstone Cluster Snap Clips 2 Pack
Add some pretty shine while keeping your stylish tresses in place with these snap clips! The two pack is adorned with multi-colored gemstone clusters for a glitzy vibe.Style Number/Barcode: 07006-0080
Category Name: Vacation Looks
Price: $6.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Eyelash Knit PJ Romper
Stay in and cozy on up for the night in this adorable eyelash knit PJ romper!
Fit & Features
- Long fitted sleeves
- Scoop neckline | Partial snap button down front
- Fitted shorts
- Fuzzy eyelash knit fabric
- Plenty of stretch
Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 07103-0062
Category Name: Vacation Looks
Price: $3.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Try Me Rhinestone Hair Clips
You say a messy bun can't look glam? Tryyy mee girrrl! These rhinestone hair clips have got all the glam u need!
- Set of two hair clips
- Over-sized design
- Rhinestone embellished
- Snap closure
Style Number/Barcode: 07006-0078
Category Name: Vacation Looks
Price: $6.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Dainty Touch Pendant Necklace
Just a little dainty something to take your look up a notch bby!
- Single necklace
- Double layered
- Dainty design
- Beading
- Double hammered pendant accents
- Lobster clasp closure
Style Number/Barcode: 07002-0280
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ruched Bubble Sleeve Cropped Blouse
Pretty and classic, this bubble sleeve blouse will be sure to dress up your everyday 'fit!
Fit & Features
- Tie front neckline
- Long ruched bubble sleeves with ruffled hems
- Elastic banded cropped hem
- Sheer chiffon fabric | No stretch
Style Number/Barcode: 06003-0641
Category Name: Vacation Looks
Price: $11.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sea Slayin' Cabby Hat
You keep slayin' in this high-seas inspired hat. This cap features a faux leather contrast, a braided detail with button detail, and has a textile main.Style Number/Barcode: 07302-0016
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale