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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Sunset Siren Cutout Bodycon Mini Dress
Serving sunkissed goddess with zero effort. This cutout bodycon mini dress hugs in all the right places, with sun-shaped hardware that turns a simple night out into a full-style statement.
Fit & Features
- Textured knit fabric, high stretch
- Strapless sweetheart neckline
- Dual cutouts at the bodice
- Metal sun-shaped hardware accents
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000445
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Petals On Repeat Floral Tube Top
This is what you wear when the group chat says, “dress cute.” The floral tube top hugs in all the right places and gives you that effortless, vacation-coded look without overthinking it.
Shop The Matching Skirt: Floral Confidence Maxi Skirt
Fit & Features
- Tropical statement floral print
- Mesh fabric with smooth knit lining
- Strapless neckline, non-slip grip lining
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000475
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bold And Sleek Abstract Animal Print Maxi Dress
She’s bold, she’s sleek, and she does not blend in. This abstract animal print maxi dress skims your curves with a draped cowl neckline and open tie-back detail that feels daring yet elevated—perfect for rooftop nights, birthday dinners, or any plan worth dressing up for.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Abstract animal print
- Sleeveless low cowl neckline
- Halter tie-back straps, open back, lower tie-back spaghetti straps
- Maxi-length form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-000735
Category Name: Vacation Looks
Price: $14.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Nicki Beaded Fringe Mermaid Formal Dress
Special Occasion
Designed for the kind of entrance that feels quietly iconic, the Nicki beaded mesh mermaid silhouette moves with intention and undeniable polish. A beaded triangle bust with fringe and a high front slit brings just enough drama to a look made for weddings, galas, and unforgettable nights.
Fit & Features
- Smooth knit-lined fabric, moderate stretch
- Beaded triangle bust silhouette with fringe
- Halter spaghetti strap
- Back zipper and hook-eye closure
- Mermaid silhouette with high front slit
- Floor-length hem
- Runs true to size
Where to Wear:
Prom, big birthday events, fashion-forward soirees, upscale cocktail parties, glamorous occasions, red-carpet events
Style Number/Barcode: 05002-001093
Category Name: Vacation Looks
Price: $19.97 $99.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Addison Animal Print Formal Dress
Special Occasion
A little daring, a lot refined, the Addison dresswas made for the kind of entrance that lingers long after you’ve crossed the room. Designed in striking animal print with a sculpted mermaid fit, this gown features a cutout bodice with a hoop insert and an open strappy back finished with beaded tie-back straps for a look that feels equal parts polished and unforgettable.
Fit & Features
- Animal print mesh fabric, knit lining
- Plunging neckline with cutout bodice, padded bra cups
- Hoop insert detail at the center front
- Open strappy back with beaded tie-back straps
- Floor-length mermaid silhouette
- Runs true to size
Where to Wear:
Destination weddings, resort dinners, vacation, honeymoons, date night, cocktail parties, birthday parties, bachelorettes
Style Number/Barcode: 05002-000713
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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Sheer Confidence Ruffled Mesh Sarong
This is the layer that turns a simple bikini into a full look. This ruffled mesh sarong hugs in all the right places with a flirty tie-waist and sheer finish that was made for beach clubs, pool parties, and spontaneous golden hour plans.
Fit & Features
- Sheer mesh fabric with high stretch
- Tie-waist design
- Long ruffled accents
- Mini-length ruffled hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 07105-000036
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK, MINT
Available Size: L/XL
Product Badge:- Sale
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Chic Mood Rectangle Sunglasses
Mood set before the outfit. These chic sunglasses feature a sleek rectangular frame with tinted lenses that instantly sharpen up your off-duty 'fits, coffee runs, and last-minute plans.
Fit & Features
- Rectangular-shaped plastic frame
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000111
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
- Rectangular-shaped plastic frame
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Sleek Confidence Curved Rectangle Sunglasses
These curved rectangle sunglasses bring sleek confidence with a lightweight metal frame and polarized tinted lenses that keep everything looking sharp from brunch to beach days.
Fit & Features
- Curved rectangular shape
- Thin metal frame
- Rubber nose pads
- Polarized tinted lenses
Style Number/Barcode: 07008-000112
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Garden Floral Cowl Neck Maxi Dress
Serving soft glam with a flirty twist. This floral cowl neck maxi dress drapes effortlessly through the neckline and skims the body for a dreamy silhouette made for weddings, vacations, and any dressy event.
Fit & Features
- Floral print, knit-lined fabric
- Cowl neckline
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001147
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Seaside Glamour Crochet Strapless Mini Dress
Serving seaside glamour. This seashell crochet mini dress hugs in all the right places, with a strapless sweetheart neckline and textured crochet knit, ready for beach clubs, sunset dinners, and every vacation photo moment.
Fit & Features
- Sheer crochet knit fabric with lining
- Seashell embellishments
- Strapless sweetheart neckline, padded bust
- Back zipper closure
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000430
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bold Bloom Floral Knit Midi Tube Dress
Big blooms, bold plans. This floral knit midi tube dress hugs in all the right places with a sleek bodycon fit and effortless strapless neckline—perfect for brunch dates, rooftop drinks, or any moment that deserves a standout look.
Fit & Features
- Ribbed knit fabric, moderate stretch
- Large floral print
- Strapless neckline
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000344
Category Name: Vacation Looks
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Glow Up Thong Wedge Heels
The kind of heels that glow with each step. These metallic thong wedges give you height without the drama, adding that polished finish to your favorite looks.
Fit & Features
- 3" Wedge heel
- Square toe
- Thong-style toe strap
- Metallic faux leather material
- Runs true to size
Style Number/Barcode: 07406-000040
Category Name: Vacation Looks
Price: $32.90
Availability: Out of Stock
Product Badge:- Ships Free
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Hotter Than Summer Bikini Bottoms
Booked the trip just to wear this. These bikini bottoms serve sculpted support with cheeky coverage and beaded detail, plus adjustable side ties that let you customize the fit before you hit the pool. Style with the matching bikini top.
Shop Matching Top: Hotter Than Summer Bikini Top
Fit & Features
- Smooth stretch knit fabric
- Low-rise waist
- Adjustable side ties with beaded accents
- Cheeky fit
- Returns are not accepted without the hygienic liner
- Runs true to size
Style Number/Barcode: 07105-000041
Category Name: Vacation Looks
Price: $9.97 $25.90
On Sale: Yes
Availability: In Stock
Available Color: RUST
Available Size: M
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Vacay Sparkle Tropical Sequin Mini Dress
Booked the trip and packed the drama. This tropical floral sequin tube bodycon mini dress hugs close with a glossy, light-catching finish that was made for sunset cocktails and flash photography.
Fit & Features
- Tropical floral, sequin mesh fabric, sewn-in lining
- Tube strapless neckline, non-slip grip lining
- Side zipper and hook-eye closure
- Bodycon mini fit
- Runs true to size
Style Number/Barcode: 05102-000427
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
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Effortless Drama Bodycon Mini Dress
Giving sultry with a twist, this leopard mini dress knows how to steal the spotlight. The ruffled sash detail takes your bodycon moment to the next level—perfect for parties, dates, or that glam night out.
Fit & Features
- Leopard print, mesh-lined fabric, moderate stretch
- Strapless tube neckline, padded bra cups
- Bodycon silhouette
- Mini-length hem, side ruffled sash detail
- Runs true to size
Style Number/Barcode: 05103-000859
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacation Coded Floral Maxi Dress
This tropical floral print maxi drapes in airy mesh with a soft cowl neck and lace-up back, flowing into a floor grazing hem that moves like you planned this getaway all along. Perfect for weekend and long getaways, where the sun will shine on you in this gorgeous dress!
Fit & Features
- Tropical floral print, mesh fabric, soft knit lining
- Cowl neck, spaghetti straps
- Lace-up back
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000990
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Plans Animal Print Mesh Halter Mini Dress
Wild plans call for a dress that knows exactly what it’s doing. This animal print mesh halter mini dress hugs through the waist with ruched shaping and flares out with playful tiers that move with you from dinner reservations to wherever the night decides to go.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Animal print
- Sleeveless halter neckline with tie-back straps, partially open back
- Metal hardware accent, keyhole bust cutout
- Ruched drop waist
- Tiered ruffled design, mini-length A-line fit
- Runs true to size
Style Number/Barcode: 05102-000350
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Radiant Shine Tube Mini Dress
Like sunshine you can wear. This glitter mesh tube mini dress features a soft A-line shape that gives a flattering, flirty fit while the subtle shimmer catches the light for brunch plans, vacations, and warm night outings.
Fit & Features
- Glitter mesh fabric, soft knit lining
- Strapless tube neckline
- A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05103-000732
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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High Impact Floral Mesh Maxi Dress
This floral mesh halter maxi dress features a draped cowl neckline and curve-hugging silhouette that flows into a sleek maxi length, perfect for date nights, vacations, and dressy events.
Fit & Features
- Floral print, mesh-lined fabric
- Cowl halter neckline
- Open back
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000683
Category Name: Vacation Looks
Price: $49.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Citrus A-Line Mini Dress
Like sunshine in outfit form. This lemon print stretch linen mini dress features a square neckline with a delicate bust tie and a flirty A-line skirt that’s made for brunch dates, vacations, and sunny day plans.
Fit & Features
- Citrus print, cotton-blend woven fabric, woven lining
- Square neckline with tie front
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- A-line fitted silhouette, pipe trim
- Flared mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000518
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Days Strappy Platform Wedges
These wedges understood the assignment. Strappy knotted details, and a cork platform wedge give you that easy lift while keeping the vibe effortless for brunch plans, coffee shops, or warm weather getaways.
Fit & Features
- 4" Wedge heel
- Square toe, strappy design
- Platform sole
- Luxe fit cushioned insole
- Adjustable ankle strap with buckle closure
- Cork/ faux leather material
- Runs true to size
Style Number/Barcode: 07406-000031
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: WHITE, GOLD
Available Size: 7.5, 9
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Casual Cutie Platform Thong Wedges
Your everyday flip-flop just got an upgrade. These platform thong wedge sandals give you a clean, minimal look with extra height and an easy slip-on fit that works from coffee runs to weekend plans.
Fit & Features
- Wedge heel
- Square toe
- Wide thong toe strap
- Wedge platform sole
- Cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07406-000038
Category Name: Vacation Looks
Price: $32.90
Availability: Out of Stock
Product Badge:- Ships Free
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Sunkissed Edge Snake Print Triangle Bikini Top
A little wild, a lot confident. This snake print triangle bikini top features a sleek, minimal look with adjustable straps and a tie-back design that lets you customize the fit your way. Style with the matching bikini bottoms.
Shop Matching Bottoms: Sunkissed Edge Snake Print Bikini Bottoms
Fit & Features
- Smooth stretch knit fabric
- Snake print
- Triangle design
- Adjustable spaghetti straps
- Open back, tie-back spaghetti straps
- Runs true to size
Style Number/Barcode: 07104-000023
Category Name: Vacation Looks
Price: $6.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Golden Coast Hoop Detail Bikini Top
This bikini top is serving effortless allure with attitude. The classic triangle silhouette gets an upgrade with hoop insets and sleek wraparound straps that highlight your shape from every angle. Shop the matching bikini bottom.
Shop Matching Bottoms: Golden Coast Hoop Detail Bikini Bottoms
Fit & Features
- Sleek knit fabric
- Triangle bust with hoop insert
- Wrap-around tie detail
- Adjustable spaghetti straps
- Tie-back detail
- Runs true to size
Style Number/Barcode: 07104-000024
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: M
Product Badge:- Sale