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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Subtle Bite Tooth Charm Three Pack Necklace Set
Minimal layers with a hint of attitude. This three-pack necklace set mixes clean chain textures with a subtle tooth charm, giving your everyday looks a little edge without overdoing it.
Fit & Features
- Three-pack necklace set
- Mixed chain designs with polished shine finish
- Tooth charm
- Lobster clasp closures
Style Number/Barcode: 07002-000419
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Going Somewhere Wrap Slit Maxi Skirt
Easy confidence, built in. This high-rise skirt hugs smoothly with a slinky double-lined knit and a front wrap slit that brings just enough drama for day or night plans.
Fit & Features
- Slinky double-lined knit fabric with stretch
- High-rise waist
- Body-skimming silhouette
- High front wrap slit for movement
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06501-000120
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Easy Does It Rib Knit Mini Skort
Easy, flattering, and always in rotation. This rib knit mini skort sits just right at the waist with side slits that add movement—perfect for everyday plans that turn into something more.
Fit & Features
- Stretch rib knit fabric
- Mid-rise waist
- Bodycon fit
- Side slit accents
- Mini-length skirt overlay, knit shorts lining
- Runs true to size
Style Number/Barcode: 06503-000227
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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After Hours Floral Leopard Mini Dress
Fluid, flattering, and impossible to ignore. This halter mini dress mixes floral and leopard-inspired abstract prints with ruched details and cascading ruffles that have all eyes on you.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Floral leopard print
- Ruffled trim V-neckline, halter tie-back straps, partially open back
- Ruffled trims, ruched detailing
- Mini-length asymmetric hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-000689
Category Name: Vacation Looks
Price: $45.90
Availability: In Stock
Available Color: MAUVE
Available Size: XS, S, M, L, XL
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Sharp Turn Aviator Sunglasses
Sleek lines, zero effort required. These trendy aviator sunglasses bring a modern edge to everyday looks, with a bold frame that instantly pulls everything together—from casual errands to styled-up moments.
Fit & Features
- Sleek aviator silhouette
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000127
Category Name: Vacation Looks
Price: $11.90
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Bloom Cowl Halter Maxi Dress
Bold print, barely-there feel perfect for vacations. This maxi dress blends leopard and tropical florals with a plunging cowl halter and open back, finished with a statement floral hardware that stands out.
Fit & Features
- Tropical floral and leopard print
- Sheer mesh fabric, soft knit short lining
- Plunge cowl halter neckline
- Open back, lower ruched seam
- Front tropical floral hardware piece
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000401
Category Name: Vacation Looks
Price: $48.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sunlit Plans Halter Tiered Skater Dress
Soft, flirty, and made for daylight plans that turn into something more. This halter skater dress balances a sculpted top with a playful tiered skirt for an easy look that feels styled the second you slip it on.
Fit & Features
- Smooth stretch fabrication
- Halter neckline with scoop front
- Drop waist with tiered skater skirt
- Mini length silhouette
- Runs true to size
Style Number/Barcode: 05102-000457
Category Name: Vacation Looks
Price: $43.90
Availability: In Stock
Available Color: YELLOW
Available Size: L
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Vacation Mode Abstract Open Back Maxi Dress
This dreamy mesh maxi dress was made for golden hour plans, tropical cocktails, and dancing 'til dinner. Designed in an abstract print that brings the ocean and desert sky together, this halter dress features a draped cowl neckline, hardware straps, and open tie-back.
Fit & Features
- Abstract print, mesh-lined fabric
- Plunge cowl halter neckline with hardware
- Open tie-back design
- High side slit
- Form-hugging maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000409
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M, L
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Soft Focus Florals Mesh Maxi Dress
Soft-focus florals, but make it a statement. This floral mesh maxi dress hugs just right with a sleek, fitted silhouette that’s ready for weddings, date nights, and every dressed-up plan on your calendar.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Large floral print
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Fitted silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000363
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Sheer mesh fabric with knit lining, high stretch
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Casually Polished Criss Cross Sandals
Easy, but never boring. These faux leather flat sandals bring subtle shine with faux pearls and stone embellishments, making them the kind of pair that upgrades even your most effortless looks.
Fit & Features
- Square toe
- Criss-cross straps with faux pearl and stone embellishments
- Faux leather material
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-000061
Category Name: Vacation Looks
Price: $22.90
Availability: In Stock
Available Color: IVORY
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Sweet Steps Bow Thong Sandals
Soft details, effortless charm. These bow thong sandals add a delicate finishing touch with a dainty bow and rhinestone-embellished accents that feel polished yet glam—perfect for casual plans, brunch dates, and shower celebrations!
Fit & Features
- Square toe
- Thong strap silhouette, bow with rhinestone embellishments
- Flat sole
- Slip-on style for easy wear
- Runs true to size
Style Number/Barcode: 07404-000058
Category Name: Vacation Looks
Price: $18.90
Availability: In Stock
Available Color: WHITE, NUDE
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Pretty Agenda Floral Woven Ruffle Maxi Dress
Soft, flowy, and ready for every RSVP on your calendar. This pretty floral woven maxi dress brings effortless drama with tiered ruffles and a flattering sweetheart neckline that looks just as good in photos as it does in motion.
Fit & Features:
- Lightweight woven fabric with full-length stretchy knit lining
- All-over floral print
- Sleeveless sweetheart neckline with ruched bust, adjustable tank straps
- Open back with self-tie detail, lower back zipper with hook-eye closure
- Tiered ruffled design
- Maxi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-000876
Category Name: Vacation Looks
Price: $54.90
Availability: Out of Stock
Product Badge:- Ships Free
- Lightweight woven fabric with full-length stretchy knit lining
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Flirty Babe Polka Dot Mesh Ruffle Mini Dress
Flowy, flirty, and impossible to ignore. This polka dot mesh ruffle mini dress hugs in all the right places with soft ruching and a playful hem that moves with you.
Fit & Features:
- Mesh fabric with knit lining, high stretch
- All-over polka dot print
- Sleeveless plunging V-neckline
- Tie-back halter straps, partially open back
- Ruched body, drop waist design
- Tiered ruffled mini-length hem, fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000515
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: XS
- Mesh fabric with knit lining, high stretch
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Sunkissed Ruffles Floral Mini Dress
Made for slow walks through seaside towns and golden hour selfies. This floral mini dress brings soft romantic vibes with a sweetheart neckline and tiered ruffles that move with you.
Fit & Features
- Chiffon fabric with floral print, knit lining
- Ruched sweetheart neckline with adjustable spaghetti straps
- Ruched fitted bodice with back zipper and hook-eye closure
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000558
Category Name: Vacation Looks
Price: $54.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
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Sunset Plans Chevron Crochet Maxi Dress
This chevron crochet knit maxi dress features a flattering V-neck and lace-up back that feels equal parts stylish and unforgettable—perfect for beachside restaurants or warm nights out.
Fit & Features
- Chevron striped pattern
- Crochet knit lined fabric
- V-neck, spaghetti straps
- Lace-up back
- Maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000418
Category Name: Vacation Looks
Price: $54.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L, XL
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One And Done Halter Wide Leg Jumpsuit
Slip it on and let the silhouette do the work. This knit cutout halter wide-leg jumpsuit hugs where it should, flows where it matters, and delivers instant confidence from day plans to night.
Fit & Features
- Lined knit stretch fabric
- Halter neckline with tie closure
- Cutout bodice
- Wide-leg fit
- Runs true to size
Style Number/Barcode: 06502-000074
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Easy Elegance Stone Beaded Thong Flat Sandals
The kind of detail that makes a simple outfit feel finished. These flat sandals feature a stone-beaded Y-shaped thong strap with delicate trim, bringing just enough shine to elevate everyday looks and dressed-up plans.
Fit & Features
- Almond toe
- Y-shaped thong strap with beaded stone embellishments
- Adjustable ankle strap with buckle closure
- Colored edge trim for detail
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-000062
Category Name: Vacation Looks
Price: $21.90
Availability: In Stock
Available Color: BLACK, TAN
Available Size: 5.5, 6, 6.5, 7, 7.5, 9, 8.5
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Easy Goes With Everything Thong Sandals
The pair you grab without thinking—because they always work. These thong sandals keep it clean and minimal with a sleek silhouette that slides effortlessly into everyday plans, from coffee runs, casual plans, or sunset walks on vacation.
Fit & Features
- Sleek square toe
- Thong strap
- Flat sole designed for everyday comfort
- Slip-on silhouette for easy on and off
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-000056
Category Name: Vacation Looks
Price: $9.97 $15.90
On Sale: Yes
Availability: In Stock
Available Color: GREEN, RED
Available Size: 5.5, 6, 6.5, 7, 7.5, 8.5, 9
Product Badge:- Sale
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Laid Back Babe Denim Skort
Denim but make it flirty. This midrise skort gives you that vintage mini look with the confidence of built-in shorts, perfect for brunches, coffee shop hangs, and night-out plans.
Fit & Features
- Tinted denim fabric
- Mid-rise waist
- Form-hugging fit, mini-length hem
- Shorts lining
- Front button closure, belt loops, pockets
- Runs true to size
Style Number/Barcode: 06603-000145
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S, M, L, XL
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Dressy Plans Cutout Jumpsuit
Sleek, sultry, and made for late plans. This halter jumpsuit serves confident cutouts and a fluid, wide leg that moves effortlessly from drinks to dance floor moments.
Fit & Features
- Smooth knit fabric
- Halter neckline, multiple styling options
- Cutout accent
- Wide-leg fit
- Runs true to size
Style Number/Barcode: 06502-000077
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: PLUM
Available Size: XS, S, M, L
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Alluring Chic Ribbed Knit Belted Mini Dress
Confident curves, chic allure. This ribbed knit mini dress hugs in all the right places with a belted waist that pulls the look together for nights out, date plans, or anytime you want effortless polish with a little edge.
Fit & Features
- Ribbed knit fabric with high stretch
- Sleeveless scoop neckline
- Tie-back halter straps, partially open back
- Attached O-ring belt detail at the waist
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000283
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: BROWN, BLACK
Available Size: S, M, L, XS
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Confidently Bold Strappy Faux Leather Tube Top
Confidently bold will be your vibe in this strappy faux leather tube top. It hugs you in all the right places and turns even a low-effort outfit into something undeniably intentional.
Fit & Features
- Strapless bandeau silhouette
- Front cutout with strappy wrap detail
- Lace-up back for adjustable fit
- Mid-length hem, form-hugging fit
- Faux leather fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06003-000216
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: L
Product Badge:- Sale
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Beachside Bold Abstract Print Beaded Bikini Top
Sun on your skin, confidence on repeat. This abstract print bikini top brings a cool edge with beaded details that feel styled and trendy—perfect for beach days that turn into golden-hour plans. Pair with the matching bikini bottoms.
Shop Matching Bottoms: Beachside Bold Abstract Print High-Cut Bikini Bottoms
Fit & Features
- Smooth stretch knit fabric, abstract print
- Triangle design
- Beaded accents on the straps and at the center
- Adjustable spaghetti straps
- Tie-back straps
- Runs true to size
Style Number/Barcode: 07104-000017
Category Name: Vacation Looks
Price: $25.90
Availability: In Stock
Available Color: MULTI
Available Size: S, M, L
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Cool Confidence Animal Print Halter Top
A halter top that knows exactly what it’s doing—draped, sculpted, and ready to flex your confidence. The mesh fabric and abstract animal print bring that cool-girl edge. Style with the matching maxi skirt.
Shop Matching Bottoms: Cool Confidence Animal Print Mesh Maxi Skirt
Fit & Features
- Mesh fabric, high stretch
- Abstract animal print
- Sleeveless plunging cowl neckline, bar strap detail
- Tie-back halter spaghetti straps
- Open back, lower tie-back spaghetti straps
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-000387
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: RUST
Available Size: XS, S, M, L
Product Badge:- Part of a Set