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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Caught Up Beaded Crop Top
The top that makes every mirror selfie worth posting. This crop top brings just the right amount of shine, serving a flattering curve-hugging fit and a striking open back that keeps all eyes on you.
Shop Matching Bottoms: Caught Up Beaded Maxi Skirt
Fit & Features
- Slinky knit stretchy fabric
- Plunge halter neckline
- Strappy beaded embellished open back
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000694
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Aloha For Now Flower Hair Pin Set
Say aloha to your new vacay-inspired look. These hibiscus flower hair pins add a playful tropical touch to ponytails, buns, and beach-day looks with a bloom for every mood.
Fit & Features
- Hibiscus flower designs
- Metal clip closures
- Three-pack set
Style Number/Barcode: 07006-000159
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Low Key Luxe Tinted Sunglasses
The kind of sunglasses that make even a simple outfit feel a little more polished. Featuring slim metal frames and warm brown-tinted lenses, this pair delivers a sleek, vintage-inspired finish.
Fit & Features
- Sleek round frames
- Rubber nose supports
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000165
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
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Lei It On Me Flower Chain Belt
The outfit was cute, then the flower chain belt showed up. Finished with sculpted hibiscus blooms, this statement belt brings vacation-ready charm to bottoms, swimsuits, and everything packed in between.
Fit & Features
- Hibiscus flower designs
- Polished shine finish
- Chain
- Lobster clasp closure
Style Number/Barcode: 07301-000397
Category Name: Vacation Looks
Price: $16.90
Availability: Out of Stock
Product Badge:- Ships Free
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Destination Darling Floral Crop Top
Vacation mode looks good on you. This floral halter top pairs a draped neckline with an open back silhouette for the kind of outfit perfect for every getaway plan.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Tropical floral print
- Sleeveless cowl neckline
- Tie-back halter straps, open back
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000675
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: In Stock
Available Color: MULTI
Available Size: XS
Product Badge:- Sale
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Paradise Glow Tropical Sequin Beaded Mini Dress
Vacation booked or not, this tropical sequin beaded mini dress is already packed for the plot. The stretchy lined mesh hugs close with a square neckline, strappy back cutout, and just enough shine to make every entrance feel intentional.
Fit & Features
- Tropical printed mesh fabric with knit lining, high stretch
- Sequin and beaded swirl embroidered pattern
- Sleeveless square neckline
- Adjustable spaghetti straps
- Lower back cutout
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000878
Category Name: Vacation Looks
Price: $13.97 $59.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: XS, S
Product Badge:- Sale
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Meet Me In Maui Mesh Maxi Dress
Covered in oversized tropical blooms and saturated sunset shades, this mesh midi dress brings vacation energy, whether you're headed to dinner by the water or a relaxing cruise.
Fit & Features
- Tropical print, lined mesh fabric with stretch
- Strapless neckline
- Bodycon silhouette
- Fitted maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000763
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: S, M, L
Product Badge:- Sale
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Ruffle Rush Tropical Floral Mini Dress
Booked trip or just booking attention, this tropical floral ruffle mini dress gets the invite. The stretchy lined mesh, halter cowl neckline, open back, and flowy ruffled sash bring flirty movement with a fitted A-line shape.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Tropical floral print
- Sleeveless cowl neckline
- Tie-back halter straps, open back, lower tie-back spaghetti straps
- Asymmetric tiered ruffled design, ruffled side sash accent
- Mini-length hem, fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000624
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- Sale
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Flirty Forecast Halter Ruffle Mini Dress
Cue the entrance, this halter ruffle mini dress came ready to flirt. The high-stretch knit sculpts with ruching through the waist, a deep V-neckline, and tiered ruffles that bring movement without overthinking the outfit.
Fit & Features
- Sleek knit fabric, high stretch
- Sleeveless deep V-neckline, beaded hardware accents
- Tie-back halter straps, partially open back
- Ruched detailing, drop waist
- Tiered ruffled design, mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05103-001139
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: PINK, TURQUOISE
Available Size: XS, S
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Wild Card Cowl Halter Mini Dress
This dress doesn't do subtle, and that's exactly the point. The draped cowl neckline, daring open back, and mixed animal print make this halter mini dress the first thing you'll reach for when packing for vacation or nights out.
Fit & Features
- Mixed animal print, knit-lined fabric
- Plunge cowl halter neckline, tie straps
- Open tie back
- Bodycon mini-length fit
- Runs true to size
Style Number/Barcode: 05103-001060
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
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Hailie Tropical Floral Lace Formal Dress
Special Occasion
Designed for the guest list that calls for something unforgettable, the Hailie dress brings together tropical lace, cascading ruffles, and a sculptural orchid accent for a look that feels equal parts romantic and statement-making. The plunging halter neckline, open back, and mermaid silhouette create striking movement from every angle.
Fit & Features
- Tropical floral print, lace fabric, smooth knit lining
- Plunge ruffled halter neckline, tie straps
- Front tropical flower pin
- Open tie-back, lower zipper and hook-eye closure
- Cascading ruffle trim
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, vacations, honeymoons, resorts, cruises, engagement parties, cocktail events, birthday dinners, date nights, summer galas, yacht parties
Style Number/Barcode: 05002-001583
Category Name: Vacation Looks
Price: $29.97 $79.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
Product Badge:- Sale
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Seaside Stunner Halter Maxi Dress
The kind of dress that makes an entrance. With a textured finish, beaded cutout details, and a sleek halter neckline, this maxi dress is perfect for vacations, bridal celebrations, and brunch dates.
Fit & Features
- Sweater knit fabric, knit lining
- Halter neckline, tie straps
- Cutout bust with beaded accents
- Center back slit
- Bodycon maxi silhouette
- Runs true to size
Style Number/Barcode: 06005-000326
Category Name: Vacation Looks
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beach Treasures Earrings Pack
This 20-piece earring set is packed with beach-inspired details, from shells and starfish to palms and pearls, making it the perfect mix-and-match collection for vacations, weekend plans, and everyday styling.
Fit & Features
- 20-piece earring set
- Various styles and beach-inspired designs
- Faux pearls and rhinestone embellishments
- Polished metal finish
- Post-back and omega closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000416
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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Georgina Glitter Cutout Formal Dress
Special Occasion
The Georgina formal dress blends shimmering glitter knit fabric with a sleek, form-hugging long silhouette. A sleeveless halter sweetheart neckline with hardware stone and ball inserts, side cutout bodice, hoop detail, and high side slit create a look that feels equal parts polished and unforgettable.
Fit & Features
- Glitter knit fabric, smooth knit lining, high stretch
- Halter neckline, padded bra cups, hardware stone and ball inset
- Adjustable spaghetti straps
- Side bodice cutout, hoop waist insert
- High side slit
- Form-hugging long-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, cocktail celebrations, birthday dinners, vacations, honeymoons, resort getaways, date nights, luxury cruises, yacht parties
Style Number/Barcode: 05002-001423
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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After Hours Bloom Floral Maxi Dress
Sleek, sculpted, and made to linger in the memory. This mesh maxi dress features a square neckline and a curve-hugging fit that feels elevated enough for dressy occasions and vacay.
Fit & Features
- Stretch mesh fabrication with smooth lining, floral print
- Spaghetti straps with a square neckline
- Fitted bodice through the hips
- Curve-hugging fit, flared maxi hem
- Runs true to size
Style Number/Barcode: 05101-000721
Category Name: Vacation Looks
Price: $19.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Sale
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Vivid Escape Ruffle Halter Mini Dress
A bold mix of prints and flowing movement makes this one impossible to overlook. This printed mini dress features a halter neckline, plunging front, and layered ruffle hem that creates dimension with every step. Perfect for vacations, day parties, and warm-weather plans that deserve something a little more memorable.
Fit & Features
- Lined mesh fabric
- Halter neckline with plunging front detail
- Mixed floral and animal print design
- Form-hugging fit
- Layered ruffle mini hem with cascading side ruffle
- Runs true to size
Style Number/Barcode: 05103-000937
Category Name: Vacation Looks
Price: $46.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S
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Simply Elevated Cork Wedges
Simply elevated is the vibe. These cork wedges pair a knotted woven toe strap with slim adjustable ankle straps and the luxe fit cushioned insole for polished height that moves from brunch to rooftop plans with ease.
Fit & Features
- 5" Cork wedge heel
- Open almond-shaped toe
- Woven toe strap with knot design
- Thin adjustable ankle straps, buckle closure
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07406-000037
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: IVORY
Available Size: 5.5, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Rare Find Animal Print Maxi Dress
A little wild, a little glamorous, and impossible to scroll past. This animal print mesh maxi dress pairs a sweetheart neckline, cutout details, hardware accents, and a dramatic front sash for the kind of entrance people remember.
Fit & Features
- Multi-animal print, lined mesh fabric
- Strapless sweetheart neckline
- Hardware bust insert with cascading sash
- Cutout bodice
- Curve-hugging, maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000803
Category Name: Vacation Looks
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Spritz Multi-Print Ruffle Mini Skort
Pool plans, brunch plans, “wait where are we going next?” plans. This multi-print ruffle mini skort brings the flirty vibe with a flouncy hem, low-rise fit, and hidden shorts. Pair with the matching tube top.
Shop Matching Top: Sunset Spritz Multi-Print Tube Top
Fit & Features
- Knit fabric, high stretch
- Floral and animal multi-print pattern
- Low-rise waist, ruched detailing
- Side ruffled accents
- Tiered ruffled mini-length hem, A-line fit
- Hidden built-in shorts
- Runs true to size
Style Number/Barcode: 06503-000327
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: MULTI
Available Size: XS
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Jailene Cutout Coin Charm Formal Dress
Special Occasion
Designed for the girl who never blends into the background, the Jailene formal dress is all about movement, shimmer, and statement-making confidence. Crafted from sleek slinky fabric, this halter mermaid gown features dramatic cutouts, a thigh-high slit, and cascading coin embellishments that catch the light with every step, dance, and slow-motion entrance.
Fit & Features
- Slinky knit stretchy fabric, knit lining
- Halter neckline, tie straps
- Partial open back, zipper and hook-eye closure
- Cutout bodice with coin charm-trimmed straps
- High side slit
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Vacations, honeymoons, resort getaways, destination celebrations, birthday dinners, yacht parties
Style Number/Barcode: 05002-001779
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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Floral Mood Mesh Lace-Up Tube Top
Florals with a little edge. This mesh lace-up tube top brings a sleek strapless fit, lined stretch feel, and tie-back detail made for plans that need a stronger outfit. Style with the matching maxi skirt.
Shop Matching Bottoms: Floral Mood Mesh Maxi Skirt
Fit & Features
- Mesh fabric with knit lining, high stretch
- Large floral print
- Strapless straight-across neckline, no-slip strip
- Flexible boning
- Lace-up back design, tie closure
- Mid-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000520
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Statement Maker Shield Sunglasses
Serving expensive taste with minimal effort. These shield metal sunglasses bring instant attitude to any look, whether you're heading on vacation, running errands, or making the sidewalk your runway.
Fit & Features
- Shield silhouette
- Clear tinted lenses
- 100% UV protection
- Rubber nose supports
- Metal arms with plastic trim
Style Number/Barcode: 07008-000183
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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Treasure Found Coin Charm Earrings
A little shimmer, a little movement. These teardrop hoop earrings feature a colored teardrop gem and cascading coin charm fringe that brings a boho-inspired allure to any look.
Fit & Features
- Sleek teardrop shaped hoop
- Colored gemstone charm
- Cascading mini coin charm fringe
- Fish hook with rubber stoppers
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000403
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Paradise Crush Halter Skater Dress
Serving vacation plans from every angle. This flirty mesh skater dress pairs a plunging halter neckline with an open tie-back and layered ruffle skirt for a look that's made for getaways, birthday dinners, and golden hour photos.
Fit & Features
- Multi-print lined mesh fabric, tulle trim lining
- Plunge halter neckline, tie straps
- Open dual tie back straps
- Fitted bodice
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000983
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: XS, S
Product Badge:- Sale