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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VIP Energy Animal Print Mini Dress
The group chat already wants the details. This animal print mini dress features a plunging halter neckline, curve-hugging mesh fit, and beaded trim accents that bring extra drama to every night-out plan.
Fit & Features
- Stretch mesh fabrication, sewn-in knit lining
- Plunge halter V-neckline with strappy accents, tie-back straps
- Animal print pattern
- Bodycon silhouette
- Fringe beaded mini-length hem, side slit accent
- Runs true to size
Style Number/Barcode: 05103-001138
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Kyla Leopard Metallic Slit Formal Dress
Special Occasion
The Kyla metallic leopard gown blends bold glamour with effortless sophistication. The leopard print, halter sweetheart neckline with hoop insert, and cutout bodice create a striking focal point, while the column floor length silhouette and high front slit bring graceful movement to every step.
Fit & Features
- Leopard print, metallic fabric, knit lining
- Halter sweetheart neckline, hoop insert, padded bust, tie straps
- Back zipper and hook-eye closure
- Cutout bodice, hoop insert
- High front slit
- Form-hugging floor-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, vacations, honeymoons, birthday dinners, bachelorettes, date nights, fashion-forward events, cocktail parties
Style Number/Barcode: 05002-000863
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Vacation Booked Tropical Floral Cutout Maxi Dress
This deserves a spot in your vacation photo dump. This tropical floral cutout maxi dress pairs a bodycon fit with a striking waist cutout, statement hardware detail, and a sweeping silhouette made for unforgettable entrances.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Large tropical floral print
- Sleeveless sweetheart neckline, metal hardware accent
- Adjustable spaghetti straps, partially open back
- Front waist cutout
- Maxi-length hem with high-cut side slit, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000673
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: XS, L
Product Badge:- Sale
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On Vacay Tropical Floral Bodycon Mini Dress
Your vacation photos just found their favorite outfit. This tropical floral bodycon mini dress combines a draped cowl neckline, flattering ruching, and a curve-loving fit that looks just as good at dinner reservations as it does on the dance floor.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Tropical floral print
- Sleeveless cowl neckline
- Tie-back halter straps, partially open back
- Ruched detailing, wrap-front design with flower accent
- Mini-length hem, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-001013
Category Name: Vacation Looks
Price: $22.96 $38.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
Product Badge:- Sale
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Vacay Mode Tropical Floral Maxi Tube Dress
The suitcase practically packed itself. This tropical floral maxi tube dress combines a sleek bodycon fit with an oversized floral print for a look that feels effortless, elevated, and ready for every vacation itinerary.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Large tropical floral print
- Strapless straight-across neckline
- High-cut back slit
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000688
Category Name: Vacation Looks
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Getaway Glam Tropical Floral Maxi Tube Dress
One dress, endless compliments. This tropical floral maxi tube dress combines a sleek bodycon fit with oversized blooms for a look that feels both getaway and glam.
Fit & Features
- Knit fabric with lining, high stretch
- Large tropical floral print
- Strapless straight-across neckline
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000644
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Resort State Of Mind Crochet Mini Dress
Consider this your out-of-office wardrobe in dress form. This crochet halter mini hugs in all the right places with a bodycon fit and lace-up back, making it perfect for sunset dinners, beach city strolls, and spontaneous weekend plans.
Fit & Features
- Crochet knit fabric, lined
- Halter neckline
- Bodycon mini-length silhouette
- Lace-up back detail
- Runs true to size
Style Number/Barcode: 06005-000370
Category Name: Vacation Looks
Price: $17.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: PINK, TEAL
Available Size: XS, S, M, L
Product Badge:- Sale
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Sorella Print Mesh A-Line Formal Dress
Special Occasion
The Sorella dress brings together airy mesh fabric, a leopard butterfly print, and a striking hardware insert with flowing sash detail. The plunge halter neckline and sheer A-line silhouette create graceful movement with every step, while the front center slit adds just the right amount of drama.
Fit & Features
- Multi leopard/butterfly print, mesh-lined fabric
- Plunge halter neckline, tie straps
- Open back
- Ruched bodice with hardware inset
- Center front slit
- Sheer A-line floor-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, fashion-forward events, vacations, honeymoons, resort getaways, sunset cocktail parties, date nights, yacht parties, upscale birthday dinners
Style Number/Barcode: 05002-001578
Category Name: Vacation Looks
Price: $79.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Resort Ready Beaded Crop Top
Serving elevated beachside glamour. This beaded crop top adds eye-catching texture and a luxe feel, making it the standout piece your vacation wardrobe has been waiting for.
Fit & Features
- Beaded fabrication with lining
- Crop top silhouette
- Scoop neckline
- Adjustable straps
- Runs true to size
Style Number/Barcode: 06001-000624
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Sunset Social Abstract Bikini Top
Golden hour called, and this top answered. Featuring an abstract print, beaded accents, and a flirty knotted front, this bikini top is made for rooftop cocktails, vacation nights, and every RSVP-worthy plan on your calendar.
Shop Matching Skirt: Sunset Social Abstract Maxi Skirt
Fit & Features
- Lightweight mesh fabrication, knit lining
- Cropped bikini top silhouette
- Plunging V-neckline
- Front knot detail with beaded shoulder straps
- Detachable dainty stone chains
- Open tie-back design
- Runs true to size
Style Number/Barcode: 06001-000671
Category Name: Vacation Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: In Stock
Available Color: MULTI
Available Size: S, M, L
Product Badge:- Sale
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Sunset Social Abstract Maxi Skirt
Golden hour called, and this skirt answered. Featuring an abstract print and a carefree maxi-length silhouette, this skirt is made for rooftop cocktails, vacation nights, and every RSVP-worthy plan on your calendar.
Shop Matching Bikini Top: Sunset Social Abstract Bikini Top
Fit & Features
- Lightweight mesh fabrication with short knit lining
- Mid-rise waist with dainty stone swag chains
- Abstract print design
- Beaded chain trim detail at waist
- Maxi-length silhouette
- Runs true to size
Style Number/Barcode: 06501-000172
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: MULTI
Available Size: M, L
Product Badge:- Part of a Set
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Passport Ready Sequin Sheer Knit Maxi Dress
Vacation photos called—they want this dress in every frame. This sequin embroidered sheer knit maxi dress pairs a sculpting bodycon fit with a striking hardware cutout and leg-baring slit that was made for rooftop dinners, destination weddings, and every RSVP in between.
Fit & Features
- Sheer textured knit fabric, mini-length knit lining, moderate stretch
- Sequin embroidery
- Strapless sweetheart neckline, bust cutout with asymmetric metal hardware accent
- Open tie-back design
- Maxi-length hem with high-cut side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000632
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- Sale
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Wild Card Chiffon Halter Mini Dress
This chiffon halter dress combines a bold mixed animal print, open back, and flowing hanky hem for a look that feels equal parts daring and unforgettable. Style with sandals for vacations, date nights, or parties.
Fit & Features
- Animal print chiffon fabric, lined
- Halter neckline, hardware insert, tie straps
- Open back design
- Flowy A-line silhouette
- Hanky mini-length hem
- Runs true to size
Style Number/Barcode: 05101-001177
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S
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Set The Mood Abstract Print Halter Maxi Dress
Some dresses complete the outfit. This one sets the entire mood. This abstract print halter maxi dress combines a dramatic plunging cowl neckline, sculpting ruching, and a fluid front sash for a look that feels both gallery opening and late-night dinner reservation.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Abstract print
- Sleeveless plunging cowl neckline, bar strap detail
- Tie-back halter straps, open back, lower back spaghetti straps
- Front sash accent, ruched detailing
- Maxi-length hem, bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-001173
Category Name: Vacation Looks
Price: $25.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Shay Tropical Printed Bead Mini Dress
Special Occasion
Made for the nights when blending in simply isn't on the itinerary, the Shay mini dress brings bold glamour to every RSVP. This beaded mesh dress features a sculpted strapless silhouette, intricate tropical-inspired print, and a twisted sweetheart neckline that catches attention from every angle.
Fit & Features
- Printed tropical design, beaded embellishments, mesh-lined fabric
- Strapless sweetheart neckline, padded bra cups, non-slip grip lining
- Side zipper and hook-eye closure
- Bodycon mini-length silhouette
- Runs true to size
Where to Wear:
Bachelorettes, birthday dinners, date nights, cocktail parties, fashion-forward events, vacations, honeymoons, resort getaways
Style Number/Barcode: 05001-000783
Category Name: Vacation Looks
Price: $89.90
Availability: In Stock
Available Color: BLACK
Available Size: XXS
Product Badge:- Ships Free
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Island Intentions Satin Mini Dress
The dress to pack in your suitcase. Designed with a tropical-inspired print, beaded straps, and a lace-up open back, this satin mini dress was made for oceanfront dinners and resort cocktails.
Fit & Features
- Silky satin woven fabric, smooth woven lining
- Subtle tropical print
- Square neckline
- Beaded spaghetti straps
- Lace-up open back
- Curve-hugging, mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000596
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: OLIVE
Available Size: XS
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Destination Glam Abstract Print Halter Top
Booked, busy, and dressed like the destination. This abstract print halter top features a plunging neckline and ruched fit that hugs in all the right places for rooftop dinners, resort nights, and every plan in between. Pair with the matching maxi skirt.
Shop Matching Bottoms: Destination Glam Abstract Print Maxi Skirt
Fit & Features
- Sleek knit fabric, high stretch
- Abstract print
- Sleeveless deep V-neckline
- Tie-back halter straps, partially open back
- Ruched bodice
- Mid-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000687
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Garden Glow Flower Statement Earrings
These dimensional acrylic flower earrings feature vibrant petals and a rhinestone-embellished center, making them the perfect finishing touch for vacations, brunch, and every outfit that could use a playful pop.
Fit & Features
- Dimensional flower
- Mini rhinestone embellished center
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000384
Category Name: Vacation Looks
Price: $13.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: NS
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Sunny Side Up Aviator Sunglasses
These colored aviator sunglasses bring a retro-inspired feel with an effortless cool factor that works from beach days to city strolls.
Fit & Features
- Square-shaped aviator silhouette
- Rubber nose supports
- Tinted lenses
- 100% UV protection
- Lightweight frame
Style Number/Barcode: 07008-000160
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: YELLOW
Available Size: NS
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Pretty Please Flower Earrings
Cute from every angle and impossible to overlook. These flower earrings feature delicate petal studs with dangling gem charms that add the prettiest finishing touch to looks for brunch, parties, or vacations.
Fit & Features
- Flower designs, mini rhinestone embellished center
- Dainty chain fringe
- Teardrop rhinestone charm
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000598
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: WINE
Available Size: NS
- Flower designs, mini rhinestone embellished center
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Tropical Flair Four-Pack Hair Clips Set
Your messy bun just booked a one-way ticket somewhere tropical. These tropical flower clips add the cutest little finishing touch to beach days, dinner plans, and every photo you almost didn’t post.
Fit & Features
- Four-pack hair clips set
- Tropical flowers
- Clip closure
Style Number/Barcode: 07006-000134
Category Name: Vacation Looks
Price: $3.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Worthy Tropical Floral Tube Top
One top, endless outfit screenshots. This tropical floral tube top combines a sleek strapless silhouette with adjustable drawstring details for a look that's effortlessly on-trend.
Fit & Features
- Lined mesh fabric, high stretch
- Large tropical floral print
- Strapless straight-across neckline
- Ruched side seams, adjustable drawstrings
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000619
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Desert Disco Beaded Bra Top
Made for head-turning stares. With intricate beadwork, cascading draped strands, and an open back silhouette, this statement bra top brings a festival-luxe feel that looks straight off a designer runway.
Fit & Features
- Beaded embellishments, knit fabric
- Halter neckline, tie straps
- Open back with tie
- Cascading beaded front drape
- Bra top silhouette
- Runs true to size
Style Number/Barcode: 06001-000623
Category Name: Vacation Looks
Price: $49.90
Availability: Out of Stock
Product Badge:- Ships Free
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Destination Glam Abstract Print Maxi Skirt
Booked, busy, and dressed like the destination. This abstract print maxi skirt features a ruched waist and high-cut side slit that creates a flowy fit for rooftop dinners, resort nights, and every plan in between. Pair with the matching halter top.
Shop Matching Top: Destination Glam Abstract Print Halter Top
Fit & Features
- Sleek knit fabric, high stretch
- Abstract print
- High-rise waist, ruched detailing
- High-cut side slit
- Maxi-length hem
- Flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 06501-000180
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Part of a Set