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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Night Whisper Plunge Ruffle Maxi Dress
The definition of sleek seduction. This halter maxi dress drapes in all the right places with a deep plunge neckline, ruched sides, and soft knit finish—made for those nights that call for a little mystery and a lot of confidence.
Fit & Features
- Slinky knit stretchy fabric
- Plunge halter neckline with ruffle detail
- Ruched side seams
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000571
Category Name: Vacation Looks
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Veronica Long Sleeve Cutout Formal Dress
Special Occasion
Striking from every angle, the Veronica one-shoulder gown sculpts the figure with a form-hugging fit, daring side cutout, and hardware detail at the waist. A sweeping floor-length hem with a high side slit ensures every step feels like a spotlight moment.
Fit & Features
- Smooth knit-lined fabric, moderate stretch
- One-shoulder, fitted long sleeve
- Side cutout bodice, hardware waist accent
- High side slit
- Form-hugging silhouette
- Floor-length hem
- Runs true to size
Where to Wear:
Black-tie galas, weddings, rehearsal dinners, engagement parties, holiday soirees, formal celebrations, red-carpet events, award ceremonies
Style Number/Barcode: 05002-000401
Category Name: Vacation Looks
Price: $29.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Untamed Bloom High-rise Slit Midi Skirt
Flirty, fearless, and just the right amount of wild. This skirt blends bold floral and animal prints for that effortlessly sultry vibe. The high-rise fit and flirty slit midi hem bring all the movement and attitude—no accessories required (but gold jewelry helps).
Shop The Matching Top: Untamed Bloom Tie-Front Crop Top
Fit & Features
- Floral and animal print, mesh fabric, lining
- High-rise waist
- Curve-hugging fit
- Flowy slit midi-length hem
- Runs true to size
Style Number/Barcode: 06501-000097
Category Name: Vacation Looks
Price: $7.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fierce And Refined Leopard Cowl Maxi Dress
Fierce meets refined with this leopard maxi dress made to command attention. Designed with a plunge cowl neckline and a daring high slit, it turns every step into a moment- finished with an open back and sleek hoop that makes it unforgettable from every angle.
Fit & Features
- Leopard print, mesh-lined fabric, moderate stretch
- Plunge cowl neckline, tie closure
- Open back with hoop insert
- High front slit
- Curve-hugging silhouette, maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000319
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Late Arrival Long Sleeve Maxi Dress
She’s sleek, sculpted, and definitely not shy. With a sweetheart neckline, flirty cutouts, and a high slit that plays with just enough drama, this curve-hugging maxi dress brings the heat wherever you go.
Fit & Features
- Smooth knit stretchy fabric, double-lined
- Sweetheart neckline with a hardware insert
- Fitted long sleeves
- Cutout bodice
- High front slit
- Curve-hugging, maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000646
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Edge of Allure Halter Maxi Dress
This one was made for your bold streak. The sheer mesh, curve-hugging fit, and plunging halter neckline bring instant “all eyes on me” energy—no extra effort required.
Fit & Features
- Abstract print, mesh fabric, sewn-in knit lining
- Plunge halter V-neckline, tie closure
- Open back
- Hardware cinch at waist
- Curve-hugging, sheer maxi-length hem
- Runs true to size
Style Number/Barcode: 05103-000596
Category Name: Vacation Looks
Price: $45.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Sunset Glow Abstract Print Tie-Front Top
Soft, sheer, and made for golden hour. This abstract print mesh tie-front top brings that effortless sultry vibe—flowy, flirty, and perfectly bold.
Shop Matching Bottoms: Sunset Glow Abstract Print Mesh Maxi Skirt
Fit & Features
- Sheer mesh fabric, lettuce edge hems, high stretch
- Abstract print
- V-neckline, tie-front design
- Long fitted sleeves
- Mid-length hem
- Runs true to size
Style Number/Barcode: 06202-000069
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sea You Soon Huggie Earrings Set
A little coastal charm, right where you need it. This two-pair huggie set features statement seashell details that bring easy, beachy energy to any look—no sand required.
Fit & Features
- Two pairs of huggie hoop earrings
- Seashell designs
- Polished metal finish
- Clasp closures
Style Number/Barcode: 07001-000213
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Luxe Frame Sunglasses
Step into the sunshine with these ultra-chic round sunglasses featuring gold metal frames and soft tinted lenses for that perfectly polished finish. Effortless, timeless, and made for main-character days.
Fit & Features
- Round metal frames with tinted lenses
- Gold-tone detailing with logo accents
- Polished finish
- 100% UV protection
Style Number/Barcode: 07008-000096
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Midnight Mischief Chain Maxi Dress
Made to steal the spotlight, this dress is designed to stun with a strapless bandeau bodice with an O-ring center and cascading chain details that frame the waist, finishing with a curve-hugging maxi skirt and side slit for that perfect mix of edge and allure.
Fit & Features
- Sleek knit fabric, short knit stretch lining
- Strapless sweetheart bandeau top, padded bra cups
- Hoop insert
- Detachable cascading chains
- High side slit
- Form-hugging fit, long-length hem
- Runs true to size
Style Number/Barcode: 05103-000555
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Seaside Whisper Shell Charm Bikini Bottoms
Make a splash in this dreamy triangle bikini top, featuring a soft flocked texture that gives effortless coastal-cool energy. Finished with a delicate shell charm at the center, it’s the prettiest little detail for your next sun-kissed moment.
Shop The Matching Top: Seaside Whisper Shell Charm Bikini Top
Shop The Matching Cover Up: Seaside Whisper Cover Up SkirtFit & Features
- Flocked texture-lined fabric
- Low-rise V-cut waist
- Adjustable side ties
- Cheeky bottom
- Shell charm accent
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000017
Category Name: Vacation Looks
Price: $25.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
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Seaside Whisper Shell Charm Bikini Top
Make a splash in this dreamy triangle bikini top, featuring a soft flocked texture that gives effortless coastal-cool energy. Finished with a delicate shell charm at the center, it’s the prettiest little detail for your next sun-kissed moment.
Shop The Matching Bottoms: Seaside Whisper Shell Charm Bikini Bottoms
Shop The Matching Cover Up: Seaside Whisper Cover Up SkirtFit & Features
- Flocked texture-lined fabric
- Triangle cups, removable padding
- Dual adjustable tie-back closures
- Shell charm accent
- Runs true to size
Style Number/Barcode: 07104-000010
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
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Shore Thing Starfish Belly Chain
Sun, sand, and sparkle. This dainty gold belly chain layers delicate strands with a tiny starfish charm for that subtle beach goddess vibe. Perfect over swimwear, with low-rise denim, or to add a touch of shimmer to your festival fit.
Fit & Features
- Dainty layered chain
- Starfish charm
- Lobster clasp closure
Style Number/Barcode: 07002-000237
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Shore Thing Starfish Arm Cuff
Straight from the shore, styled for the city. This starfish cuff bracelet brings a touch of seaside charm with its textured metallic finish and open wrap design. Perfect for stacking or adding a little ocean energy to any look.
Fit & Features
- Polished metallic finish
- Dual starfish ends with textured detailing
- Open cuff design
Style Number/Barcode: 07003-000166
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Golden Bloom Flower Arm Cuff
Bloom where the glam is. This floral cuff bracelet adds a feminine twist with polished petal details and an open design that’s equal parts delicate and statement.
Fit & Features
- Polished metallic finish
- Open cuff design with dual flower ends
Style Number/Barcode: 07003-000165
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday It Girl Rectangle Sunglasses
These rectangle sunnies give serious quiet-luxury energy—clean lines, chic gold V accents, and a shape that goes with literally everything. They’re the pair you grab when you want to look put-together with zero effort.
Fit & Features
- Plastic rectangle frames
- Tinted lenses
- V-shaped accents
Style Number/Barcode: 07008-000105
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Marlyne Halter Open Back Formal Dress
Special Occasion
Effortless and ethereal, the Marlyne formal dress moves like a warm breeze. Designed in airy organza fabric with a halter neckline and chic O-ring accent, its free-flowing A-line silhouette and open back create an easy elegance that’s perfect for sunset dinners or coastal soirées.
Fit & Features
- Lightweight organza shimmer woven fabric, woven lining
- Halter neckline with hoop insert, tie straps
- Open back design
- Hidden side pockets
- Flowy A-line silhouette
- Floor-length hem
- Runs true to size
Where to Wear:
Destination weddings, garden ceremonies, sunset dinner parties, resort vacations, cocktail events, bridal showers, wedding showers, rehearsal dinners, birthday celebrations
Style Number/Barcode: 05002-000751
Category Name: Vacation Looks
Price: $79.90
Availability: In Stock
Available Color: BROWN, BEIGE
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Ocean Treasures Bikini Charms
A little ocean magic for your swim looks—these gold sea life charms clip onto your bikini for an instant resort-worthy upgrade. Starfish, shells, and sandy-day sparkle make every beach moment feel a little more styled.
Fit & Features
- Three-piece charm set
- Starfish, shell, and sand dollar motifs
- Polished tone finish
- Clasp attachments
Style Number/Barcode: 07001-000225
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blossom Kiss Floral Pearl Earrings
Flirty, feminine, and a little fancy. These flower earrings feature a delicate bloom with a faux pearl accent that adds just the right touch of soft glamour.
Fit & Features
- Floral design with faux pearl drop accent
- Polished metal finish
- Post-back closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000246
Category Name: Vacation Looks
Price: $8.90
Availability: Out of Stock
Product Badge:- Ships Free
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Jeanette Cheetah Print Mermaid Formal Dress
Special Occasion
Crafted for the woman who embraces every entrance, the Jeanette formal dress shapes a striking mermaid floor-length silhouette in bold cheetah print. The halter v-neckline with hoop inserts, open back, and lower ruched seam adds sculpted allure—turning every step into a high-impact moment.
Fit & Features
- Cheetah print, mesh-lined fabric
- Halter V-neckline with hoop inserts
- Open back with lower ruched bum seam
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Fashion gala, creative industry event, luxe birthday dinners, holiday or NYE parties, resort destination weddings, upscale cocktail parties, anniversaries
Style Number/Barcode: 05002-000711
Category Name: Vacation Looks
Price: $84.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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Seaside Whisper Cover Up Skirt
For the days you want your swimsuit to have a plus-one, this scrunched cover-up brings that flirty, beach-wandering energy. With flocked shell texture and adjustable sides, it’s the piece that makes your bikini feel instantly styled.
Shop The Matching Bikini Bottoms: Seaside Whisper Shell Charm Bikini Bottoms
Shop The Matching Bikini Top: Seaside Whisper Shell Charm Bikini TopFit & Features
- Flocked texture shell pattern, knit stretchy fabric
- Low-rise waist
- Adjustable drawstring sides with ties and seashell trims
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 07105-000018
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
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Carefree Chic Strappy Sandals
Your new “grab-and-go but still cute” sandals — strappy, sleek, and finished with metallic touches that make even the simplest outfit feel styled. Lightweight, comfy, and ready for any sunny day plans.
Fit & Features
- Glossy faux patent finish
- Open round toe with toe-hardware strap
- Multi-strap design
- Adjustable ankle strap with buckle closure
- Flat sole
- Lightly padded footbed
- Runs true to size
Style Number/Barcode: 07404-000040
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Chic Lace-Up Crop Top
Meet the top that turns heads. The lace-up beaded back and crop-length silhouette give you that breezy, pulled-together vibe, and you didn't even have to think about it. Pair with the matching wide-leg pants.
Shop Matching Bottoms: Effortless Chic Wide-Leg Pants
Fit & Features
- Smooth knit fabric, high stretch
- Square halter neckline
- Spaghetti straps
- Lace-up back, beading
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000384
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: RUST
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Ocean Glow Pearl Shell Earrings
Channel full seaside siren energy with these dreamy shell drop earrings. Designed with textured gold-tone scallop shells and dainty faux pearl accents, they serve effortlessly “washed ashore but make it glam.”
Fit & Features
- Gold-tone textured shell design
- Faux pearl embellishments
- Drop-style earrings with cascading pearl dangles
- Post-back closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000231
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free