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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Layered Luxe Bracelet Five-Pack
Stacked and styled in seconds. This five-pack bangle bracelet mixes sleek metal bands with a bold hinge bangle for that effortless layered look, no overthinking required.
Fit & Features
- Five-pack bangle bracelet set
- Various styles and designs
- Hinge closure and slip-on styles
Style Number/Barcode: 07003-000196
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Petals On Repeat Floral Earrings
Soft glam, but make it playful. These floral drop earrings bring a flirty, feminine touch with cascading blooms that instantly dress up your brunch fits and date-night looks.
Fit & Features
- Linear drop silhouette
- Triple floral design
- Textured center detail
- Post back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000272
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All The Angles Textured Hoop Earrings
Minimal effort, maximum polish. These textured hoop earrings add just enough shine and detail to make your everyday fit feel styled in seconds.
Fit & Features
- Polished construction
- Medium hoop silhouette
- Textured etched front detail
- Post back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000332
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Breezy Off-Shoulder Poncho Top
That effortless throw-on and go layer. This crop poncho top drapes off the shoulder with a relaxed fit that pairs perfectly with denim, boots, and stacked jewelry for an easy, cute vibe.
Fit & Features
- Texture knit fabric
- Off-shoulder neckline
- Relaxed cropped silhouette
- Runs true to size
Style Number/Barcode: 06005-000311
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: BROWN, IVORY, WINE
Available Size: XS/S, M/L
Product Badge:- Back In Stock
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Island After Hours One Shoulder Maxi Dress
This is what you pack when the itinerary says “sunset drinks,” and you plan on being the view. The one-shoulder neckline with hardware detail gives elevates the look, while the tropical floral print and front slit keep it flowy, flirty, and very camera-ready.
Fit & Features
- Tropical floral print knit fabric
- One-shoulder neckline
- Statement hardware strap detail
- Front slit with ruffle accent
- Maxi length hem
- Runs true to size
Style Number/Barcode: 05102-000419
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Such A Flirt Polka Dot Mesh Mini Skort
Okay, but this skort just RSVP’d yes for you. This polka dot mesh mini skort drapes perfectly with a tiered ruffled design and flirty A-line fit, making it your go-to for party plans, birthday dinners, or that last-minute invite that has you walking in like you planned it all week.
Shop Matching Top: Such A Flirt Polka Dot Mesh Cowl Neck Top
Fit & Features
- Polka dot mesh fabric, high stretch
- Mid-rise waist with ruching
- Tiered ruffled design
- Mini-length overlay, A-line silhouette
- Hidden fitted knit shorts
- Runs true to size
Style Number/Barcode: 06503-000245
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK/WHITE
Available Size: L
Product Badge:- Sale
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Kim Rhinestone Leopard Mermaid Formal Dress
Special Occasion
Designed to command attention the moment you arrive, the Kim rhinestone leopard gown brings bold glamour to any formal setting. The mermaid floor-length silhouette is finished with a striking cutout back that feels confident, sculpted, and unforgettable.
Fit & Features
- Rhinestone embellished mesh-lined fabric, leopard pattern
- Plunge V-neckline, wide shoulder straps
- Side zipper and hook-eye closure
- Cutout back detail
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Prom, black-tie galas, weddings, red-carpet occasions, formal birthday celebrations, upscale receptions, fancy art gallery openings, award show dinners, special date nights
Style Number/Barcode: 05002-001039
Category Name: Vacation Looks
Price: $159.90
Availability: Out of Stock
Product Badge:- Ships Free
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Bare Minimum Drama Sequin Crochet Fringe Poncho
Sheer, shimmery, and not here to blend in. This sequin crochet fringe poncho is the ultimate layer when your bikini top or bralette deserves a little extra attention, but you still want that effortless, thrown on and thriving vibe.
Fit & Features
- Lightweight sheer crochet fabric
- Sequin embellishments
- Relaxed poncho silhouette
- Open neckline with easy slip-on design
- Fringe hem
- Runs true to size
Style Number/Barcode: 06005-000288
Category Name: Vacation Looks
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dripping In Drama Hammered Lariat Necklace
Serving poolside goddess with zero effort. This hammered lariat necklace drops low with bold statement shine, instantly elevating plunging necklines, swim looks, or that pic-worthy dress you’ve been saving.
Fit & Features
- Metal construction with hammered texture
- Long lariat silhouette
- Oversized shaped pendants
Style Number/Barcode: 07002-000371
Category Name: Vacation Looks
Price: $19.90
Availability: Out of Stock
Product Badge:- Ships Free
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Beachside Siren Mesh Swim Cover Up
Beach walk, but make it cinematic. This mesh cinched cover up hugs in all the right places with adjustable side ties and a dramatic slit, perfect for layering over your bikini when you want a little mystery with your moment.
Fit & Features
- Lightweight sheer mesh fabric
- Fitted maxi cover-up silhouette
- Mid-rise waist
- High side slit
- Ruched accents
- Runs true to size
Style Number/Barcode: 07105-000038
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: L/XL
Product Badge:- Sale
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Sun Chaser Studded Bandeau Bikini Top
Sun out, standards high. This bandeau bikini top keeps it sleek with a halter strap detail and subtle stud trim, giving you that sculpted, secure fit whether you’re beach lounging or chasing the next swim pic.
Shop Matching Bottoms: Sun Chaser Studded Bikini Bottoms
Fit & Features
- Smooth stretch fabrication
- Bandeau bikini top silhouette
- Halter neck strap for added support
- Studded trim
- Runs true to size
Style Number/Barcode: 07104-000019
Category Name: Vacation Looks
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Whimsical Charm Butterfly Claw Clip Set
Your five-minute hair routine just got a glow up. This four-piece butterfly claw clip set adds a dreamy, throwback touch to messy buns, half-up styles, and everything in between—cute, effortless, and always camera ready.
Fit & Features
- Four-piece hair claw clip set
- Butterfly designs
- Claw clip closure
Style Number/Barcode: 07006-000119
Category Name: Vacation Looks
Price: $3.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bloom Agenda Floral Mesh Halter Maxi Dress
RSVP secured and outfit handled. This floral mesh halter maxi dress sculpts with high-stretch comfort, features a statement flower hardware accent, and serves a partially open back that’s perfect for photo ops.
Fit & Features
- Sheer mesh fabric with full-length knit lining, high stretch
- Large floral print
- Sleeveless halter neckline, tie-back design
- Metal flower hardware accent
- Partially open back
- Maxi-length form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-000881
Category Name: Vacation Looks
Price: $54.90
Availability: Out of Stock
Product Badge:- Ships Free
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Compliment Me Lace Ruffle A-Line Mini Dress
This lace ruffle A-line mini dress hugs through the sweetheart bodice, shows just enough with waist cutouts, and flares into a floaty silhouette that moves when you do—perfect for parties, bridal events, or any time you want compliments on repeat.
Fit & Features
- Sheer lace fabric with lining
- Sleeveless sweetheart neckline
- Tie-back halter straps, partially open back
- Asymmetric waist cutouts leading to open lower back
- Ruffled trim
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-000867
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Soft Glam Agenda Lace Ruffle Skater Dress
Soft glam just secured your weekend plans. This lace skater dress hugs at the waist, flares into flirty ruffles, and is basically made for date night, birthday dinners, and any invite that says “dress cute.”
Fit & Features
- Lace fabric with lining
- Sleeveless deep V-neckline
- Halter tie-back straps
- Open back
- Tiered ruffled design
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 05101-001100
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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DIME Retro Slim Sunglasses
Serving vintage energy with a modern edge. These DIME slim rectangular sunglasses feature a rich mocha hue frame with tinted lenses that instantly elevate any look—from coffee runs to coastlines.
Fit & Features
- Slim rectangular frame
- Tinted lenses
- 100% UV protection
- Lightweight feel
- "Dime" logo on the arms
Style Number/Barcode: 07008-000144
Category Name: Vacation Looks
Price: $14.97 $30.00
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Slim rectangular frame
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DIME Glendale Shield Sunglasses
If the invite calls for sunny day fun, these are coming with you. These DIME oversized shield sunglasses bring bold energy with a mirrored lens and sleek arms that instantly level up any look.
Fit & Features
- Lightweight frames
- Oversized shield silhouette
- Mirrored tinted lens
- 100% UV protection
- Slim arms with "Dime" logo
Style Number/Barcode: 07008-000140
Category Name: Vacation Looks
Price: $14.97 $30.00
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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DIME Cat Eye Sunglasses
Minimal effort, maximum attitude. These DIME sleek cat eye sunglasses feature a sharp silhouette and polarized tinted lenses that instantly elevate leather jackets, slick buns, and last-minute dinner plans.
Fit & Features
- Glossy acetate frame
- Narrow cat eye silhouette
- Polarized tinted lenses with 100% UV protection
- Slim arms with "Dime" logo
Style Number/Barcode: 07008-000139
Category Name: Vacation Looks
Price: $14.97 $30.00
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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DIFF Aspyn Ovard Tortoise Sunglasses
POV: you just found the sunglasses that pull the whole outfit together. These DIFF oval sunglasses add instant cool to your everyday looks, whether you’re headed to brunch, campus, or a last-minute photo dump moment.
Fit & Features
- Smooth acetate material
- Structured oval sunglasses silhouette
- Tinted lenses with 100% UV protection
- Slim curved arms with "Diff" logo
Style Number/Barcode: 07008-000142
Category Name: Vacation Looks
Price: $98.00
Availability: Out of Stock
Product Badge:- Ships Free
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Sweetly Calculated Lace Trim Mini Dress
A little romance, a little edge. This halter mini dress hugs through the bodice, flares into an easy A-line shape, and finishes with lace trim that makes it feel styled even before you add heels.
Fit & Features
- Mesh-lined fabric, lace trim
- Halter neckline
- Partial open back
- Bodycon A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05103-000828
Category Name: Vacation Looks
Price: $44.90
Availability: Out of Stock
Product Badge:- Ships Free
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Golden Glow Strapless Maxi Dress
Serving sunkissed confidence with every step. The strapless lace maxi dress contours through the bodice, highlights the neckline with hardware detail, and falls into a sleek, elongating shape that feels equal parts elevated and effortless.
Fit & Features
- Striped design, lace-lined fabric
- Strapless sweetheart neckline, hardware insert, non-slip grip lining
- Form-hugging
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000425
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Confidence Halter Crop Top
It’s the kind of top that makes sunset cocktails turn into dinners with a view. The floral cowl halter crop top features a fluid drape, statement orchid accent, and tie-back halter neckline that feels flirty, elevated, and ready for warm nights out.
Shop The Matching Skirt: Floral Confidence Maxi Skirt
Fit & Features
- Floral pattern, mesh lined fabric
- Orchid inset, halter cowl neckline, tie straps
- Open back design
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06001-000468
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Delicate and Daring Strappy Crop Top
This beaded hanky hem top contours through the bodice, dips into a V-neckline, and ties across the open back for a barely-there finish that pairs perfectly with tailored pants or a sleek mini skirt.
Fit & Features
- Mesh-lined fabric with beaded detailing
- V-neckline with slim adjustable straps
- Fitted bodice with hanky hem
- Open back with adjustable tie closure
- Runs true to size
Style Number/Barcode: 06001-000486
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: BROWN, CHARTREUSE, PLUM
Available Size: XS, S, M, L
Product Badge:- Back In Stock
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Floral Confidence Maxi Skirt
It’s the kind of skirt that makes sunset cocktails turn into dinners with a view. The floral maxi skirt features a fluid drape, statement silhouette, and flared hem that feels flirty, elevated, and ready for warm nights out.
Shop The Matching Top: Floral Confidence Halter Crop Top
Fit & Features
- Tropical statement floral print
- Mesh fabric with smooth knit lining
- Mid-rise waist
- Curve-hugging
- Maxi flared hem
- Runs true to size
Style Number/Barcode: 06501-000116
Category Name: Vacation Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: BANANA
Available Size: L
Product Badge:- Sale