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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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: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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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: $19.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
Product Badge:- Sale
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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: $19.97 $52.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- Sale
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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: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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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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Twinkle Toes Rhinestone Strappy Sandals
That subtle shine you only notice up close. These rhinestone strappy sandals are designed to elevate everyday outfits without stealing the spotlight.
Fit & Features
- Round toe design
- Rhinestone-embellished toe and asymmetrical straps
- Flat sole
- Luxe fit cushioned insole
- Smooth faux leather material
- Runs true to size
Style Number/Barcode: 07404-000066
Category Name: Vacation Looks
Price: $20.90
Availability: In Stock
Available Color: NUDE
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9
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Untamed Energy Snake Print Swimsuit
You'll serve bold confidence in this swimsuit before you even hit the water. This snake print one-piece features a lace up front with crisscross straps and a curve-hugging fit that turns every poolside moment into a full look.
Fit & Features
- Smooth stretch swim material with snake print pattern
- Strapless neckline with adjustable straps
- Lace-up front detail
- High-cut leg design, cheeky coverage
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000033
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: SNAKE
Available Size: S, M, L
- Smooth stretch swim material with snake print pattern
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Elevated Thong Platform Wedge Sandals
The effortless height your outfits have been waiting for. These thong wedge sandals add a sleek lift with a minimal strap design that pairs perfectly with your everyday looks.
Fit & Features
- Wedge heel
- Almond toe
- Wide thong strap
- Cushioned insole
- Platform sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07406-000039
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: $25.90
Availability: In Stock
Available Color: RUST
Available Size: S, M, L
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Hotter Than Summer Bikini Top
Booked the trip just to wear this. This bikini top serves sculpted support with a ruched bust and charm detail, plus adjustable straps that let you customize the fit before you hit the pool. Style with the matching bikini bottoms.
Shop Matching Bottoms: Hotter Than Summer Bikini Bottoms
Fit & Features
- Smooth stretch knit fabric
- U-wire sweetheart neckline with ruched bust and charm detail
- Adjustable shoulder straps
- Back hook closure
- Minimal coverage fit
- Runs true to size
Style Number/Barcode: 07104-000028
Category Name: Vacation Looks
Price: $28.90
Availability: In Stock
Available Color: RUST
Available Size: S, M, L
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Sunset Swirl Lace-Up Maxi Dress
Serve vacation glow from every angle in this striped maxi dress. This dress hugs your curves while the crisscross lace-up back and flared mermaid hem bring the drama for cocktails and dinners with a view.
Fit & Features
- Striped pattern, crochet knit lined fabric
- V-neckline with tie front detail
- Spaghetti straps shape the strappy lace-up back
- Mermaid flared maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000426
Category Name: Vacation Looks
Price: $52.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L, XL
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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: $39.90
Availability: In Stock
Available Color: PURPLE
Available Size: XS, S, M, L, XL
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Siren Vibe Cutout One-Piece Swimsuit
This swimsuit was made for the kind of beach day that turns into sunset plans. The cutout one-piece swimsuit hugs with smooth stretch knit fabric, a plunging halter neckline, and a bold O-ring detail that keeps the vibe confident and a little daring.
Fit & Features
- Smooth stretch knit fabric
- Abstract tie-dye print
- Plunging V-neckline, halter strap
- Center O-ring metal accent
- Side cutouts leading to open back, tie-back spaghetti straps, high-cut cheeky fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000027
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: MULTI
Available Size: S, M, L
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Vanna Payette Sequin Crochet Column Dress
Special Occasion
Made for evenings that call for a little extra shimmer, the Vanna payette sequin crochet column dress catches the light with every step. The sleek silhouette is finished with a strappy open back and high-cut side slits, creating an effortlessly striking look from every angle.
Fit & Features
- Sheer crochet knit fabric with mesh lining, moderate stretch
- All-over payette sequin embroidery
- Sleeveless V-neckline
- Spaghetti straps with beading and seashell accents, open cross-back strappy design
- Dual high side slits
- Floor-length column silhouette
- Runs true to size
Where to Wear:
Prom, bridal celebrations, honeymoons, birthday dinners, anniversaries, formal parties, and vacations.
Style Number/Barcode: 05002-001099
Category Name: Vacation Looks
Price: $29.97 $79.90
On Sale: Yes
Availability: In Stock
Available Color: NATURAL
Available Size: XS, M, L, XL
Product Badge:- Sale
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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: $20.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XL
Product Badge:- Sale
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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: $19.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: RUST
Available Size: XS, S, M, L
Product Badge:- Sale
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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: $34.90
Availability: Out of Stock
Product Badge:- Ships Free
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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: In Stock
Available Color: BROWN
Available Size: XS
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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: $19.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
Product Badge:- Sale
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Fresh Blooms Puff Sleeve Skater Dress
Cute plans start with a dress like this. This floral skater dress features a sweetheart neckline with a flirty tie detail and an open back design that feels perfect for brunch dates, Easter, and sunny weekend plans.
Fit & Features
- Floral vineyard print, linen-like fabric with woven lining
- Sweetheart neckline with tie front detail
- Puff short sleeves with elastic cuffs
- Strappy lace-up back design
- Flowy skater short silhouette
- Runs true to size
Style Number/Barcode: 05101-000914
Category Name: Vacation Looks
Price: $19.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE-2
Available Size: XXS, XS, S, M, L
Product Badge:- Sale
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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
Available Size: 7.5, 8, 8.5, 10
Product Badge:- Best Seller
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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