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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Effortlessly Yours Slinky Knit Poncho
One of those tops that somehow works with everything and still stands out. This slinky knit poncho drapes effortlessly with an off-the-shoulder neckline and asymmetric hem that pairs perfectly with denim, shorts, or a sleek mini.
Fit & Features
- Slinky knit fabric, high stretch
- Off-the-shoulder neckline
- Short sleeves
- Asymmetric hem
- Fitted silhouette
- Runs true to size
Style Number/Barcode: 06001-000746
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: SAGE, BURGUNDY
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Bloom Service Hair Claw Clip
The finishing touch your messy bun was waiting for. This triple tropical flower hair claw clip brings a playful, vacation-ready vibe to quick updos, sleek twists, and every outfit that deserves a little extra fun.
Fit & Features
- Hair claw clip silhouette
- Triple tropical flower design
- Claw clip closure
Style Number/Barcode: 07006-000151
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: YELLOW
Available Size: NS
Product Badge:- New Arrival
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Wrist Candy Four-Pack Bangle Set
This statement four-pack bangle bracelet stack brings instant polish to everything from swimwear and sundresses to your favorite going-out look, making styling feel effortlessly pulled together.
Fit & Features
- Four-pack bangle bracelet set
- Two sleek metal bangles
- Two chunky square-shaped bangles
Style Number/Barcode: 07003-000260
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: MULTI
Available Size: NS
Product Badge:- New Arrival
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Backless Behavior Halter Mini Dress
This dress definitely started a few unnecessary crushes. The bodycon fit, cowl halter neckline, and attached triangle bikini top bring serious vacation confidence, while the side ruffle sashes and open back keep every angle working overtime.
Fit & Features
- Slinky knit fabric, knit lining
- Plunge halter cowl open neckline
- Attached string triangle bikini top
- Open back
- Bodycon mini-length silhouette
- Attached side ruffles
- Runs true to size
Style Number/Barcode: 05103-001029
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Vacation Coded Halter Tunic Top
A little daring, a little vacation-coded, and fully worth the stare. This halter tunic top brings flowy movement, a dramatic open front, and an abstract print that makes even simple plans feel expensive.
Fit & Features
- Abstract print, sheer mesh fabric, bust lining
- Sweetheart halter neckline, tie straps, hoop insert
- Center front high slit opening
- Flowy long-length hem
- Runs true to size
Style Number/Barcode: 06001-000655
Category Name: Vacation Looks
Price: $34.90
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Plans Satin Halter Crop Top
Serving date night, rooftop drinks, and every plan worth dressing up for. This satin halter top features a draped cowl neckline and an open tie-back design that creates an effortlessly elevated look from every angle.
Fit & Features
- Smooth satin fabrication
- Sleeveless plunge halter neckline
- Open back
- Adjustable neck and back tie closures
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-000583
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: GREEN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Disco Daisy Beaded Mini Skort
This skort came to collect compliments. Covered in floral beadwork and shimmering sequins with a scalloped hem, it’s the piece you throw on when the dress code is extra.
Fit & Features
- Floral bead and sequin-embellished pattern
- Sheer mesh fabric, built-in knit shorts
- Side zipper and hook-eye closure
- Form-hugging fit
- Scallop trim mini-length hem
- Runs true to size
Style Number/Barcode: 06403-000155
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Sweet Escape Cascading Ruffle Mini Skirt
Serving postcard-worthy outfits and endless outfit compliments. This cascading ruffle mini skirt features a flowy layered design that moves with every step, making it the perfect pick for vacations, festivals, and sunny-day styling.
Fit & Features
- Lightweight woven fabrication
- Low-rise silhouette
- Cascading tiered ruffle design
- Asymmetrical hem
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06503-000342
Category Name: Vacation Looks
Price: $32.90
Availability: Out of Stock
Product Badge:- Ships Free
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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
- Sleeveless v-neckline
- Animal print pattern
- Bodycon silhouette
- Beaded trim accents
- Mini length silhouette
- Runs true to size
Style Number/Barcode: 05103-001138
Category Name: Vacation Looks
Price: $42.90
Availability: Out of Stock
Product Badge:- Ships Free
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Coastal Crush Chevron Halter Romper
Out of office and dressed accordingly. This chevron halter romper features a plunging neckline with ring details and an easy-breezy fit that's made for vacations, rooftop cocktails, and spontaneous sunset plans.
Fit & Features
- Woven fabrication
- Sleeveless halter neckline
- Ring detail front with open back design
- Multi-hued chevron pattern
- Romper silhouette
- Cheeky shorts
- Runs true to size
Style Number/Barcode: 06303-000058
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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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: Out of Stock
Product Badge:- Ships Free
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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: $44.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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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: $38.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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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: $46.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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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: $54.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Dallas Mesh Print Bead Formal Dress
Special Occasion
Like a work of art in motion, The Dallas gown captivates with a printed butterfly abstract design that drifts across airy mesh fabric. The sweetheart neckline, cutout bodice, and detachable beaded straps bring a distinctive finish, while the open tie back and flowing A-line silhouette create an effortlessly striking presence.
Fit & Features
- Multi-printed mesh fabric, knit lining
- Sweetheart neckline, padded bra cups
- Spaghetti straps
- Open tie back
- Detachable beaded waist chain
- A-line floor-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, vacations, honeymoons, bachelorettes, date nights, yacht parties, birthday celebrations, luxury resorts, beach clubs, anniversaries, fashion-forward events
Style Number/Barcode: 05002-001582
Category Name: Vacation Looks
Price: $99.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
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
- Halter neckline
- Bodycon mini-length silhouette
- Lace-up back detail
- Runs true to size
Style Number/Barcode: 06005-000370
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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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, XL
Product Badge:- Ships Free
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Paradise Pending Flower Hair Claw Clip
Your updo just booked a vacation. This embellished tropical flower hair claw clip adds a playful finishing touch to messy buns, sleek twists, and every warm-weather outfit in between.
Fit & Features
- Hair claw clip silhouette
- Tropical flower design
- Embellished detailing
- Clip closure
Style Number/Barcode: 07006-000149
Category Name: Vacation Looks
Price: $8.90
Availability: In Stock
Available Color: YELLOW, FUCHSIA, PINK, WHITE
Available Size: NS
Product Badge:- New Arrival
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Resort Ready Beaded Bikini Top
Serving elevated beachside glamour. This beaded bikini 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
- Bikini top silhouette
- Scoop neckline
- Adjustable straps
- Runs true to size
Style Number/Barcode: 06001-000624
Category Name: Vacation Looks
Price: $49.90
Availability: Out of Stock
Product Badge:- Ships Free
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Vacation Glow Sequin Skort
Serving resort-ready sparkle from every angle. This sequin mini skort gives you the flirty look of a skirt with the confidence and comfort of built-in shorts, making it perfect for vacations, brunches, and sunset plans.
Fit & Features
- Sequin-embellished fabrication with lining
- Mid-rise waist
- All-over floral sequin design
- Mini length silhouette
- Built-in cheeky shorts
- Runs true to size
Style Number/Barcode: 06403-000149
Category Name: Vacation Looks
Price: $44.90
Availability: Out of Stock
Product Badge:- Ships Free
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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
- Cropped bikini top silhouette
- Plunging v-neckline
- Front knot detail with beaded shoulder straps
- Open back design
- Runs true to size
Style Number/Barcode: 06001-000671
Category Name: Vacation Looks
Price: $24.90
Availability: Out of Stock
Product Badge:- Ships Free
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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 lining
- Mid-rise foldover waistband
- 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: Out of Stock
Product Badge:- Ships Free
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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: $52.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- New Arrival