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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Floating Moment Pleated Palazzo Pants
Float through the day in these effortless pleated palazzo pants. The lightweight chiffon fabric creates soft movement with every step, while the relaxed silhouette keeps your look easy and polished. Perfect for dressing up with heels or keeping it breezy with sandals.
Fit & Features
- Chiffon-lined fabric
- High-rise waist
- Flowy wide-leg silhouette
- Pleated design
- Runs true to size
Style Number/Barcode: 06402-000031
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
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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: $25.90
Availability: In Stock
Available Color: SNAKE
Available Size: S, M, L
Product Badge:- Part of a Set
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Sunkissed Edge Snake Print Bikini Bottoms
A little wild, a lot confident. These snake print bikini bottoms feature a sleek, minimal look with adjustable side ties that let you customize the fit your way. Style with the matching bikini top.
Shop Matching Top: Sunkissed Edge Snake Print Triangle Bikini Top
Fit & Features
- Smooth stretch knit fabric
- Snake print
- Side tie closures
- Cheeky fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000032
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: SNAKE
Available Size: S, M, L
Product Badge:- Part of a Set
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Weekend Style Studded Slide Sandals
These slide sandals add just the right amount of edge with a studded design for an effortless look.
Fit & Features
- Square toe
- H-shaped band with studs
- Flat sole
- Cushioned insole
- Faux suede material
- Runs true to size
Style Number/Barcode: 07404-000046
Category Name: Vacation Looks
Price: $18.90
Availability: In Stock
Available Color: TAUPE
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Tropical Tresses Hair Claw Clip Set
Brighten your tresses with this three-pack hair claw clip set! Designed in blooming tropical florals with claw clip closures for a secure grip, these hair clips are perfect for vacations!
Fit & Features
- Three-pack hair claw clip set
- Tropical floral design
- Claw closure
Style Number/Barcode: 07006-000136
Category Name: Vacation Looks
Price: $11.90
Availability: Out of Stock
Product Badge:- Ships Free
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Golden Coast Hoop Detail Bikini Bottoms
These bikini bottoms are serving effortless allure with attitude. The classic bikini bottoms get an upgrade with hoop insets and a sleek back ruched seam that highlights your shape from every angle. Shop the matching bikini bottom.
Shop Matching Top: Golden Coast Hoop Detail Bikini Top
Fit & Features
- Sleek knit fabric
- Mid-rise fit
- Hoop side inserts
- Back ruched seam
- Cheeky bottom
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000034
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: BROWN, MINT
Available Size: S, M, L
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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: 07104-000037
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: MINT, BROWN
Available Size: S, M, L
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Goes With Everything Thong Sandals
Simple, sleek, and always in rotation. These thong sandals keep it minimal with a clean silhouette that goes with everything, making them your easy grab for errands, weekend plans, and last-minute outfit saves!
Fit & Features
- Square toe design
- Minimal thong toe strap
- Cushioned footbed
- Flat sole
- Luxe fit cushioned sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-000047
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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Shimmer Steps Rhinestone Slide Sandals
A little sparkle goes a long way. These rhinestone strap slide sandals add an easy glow to everyday outfits with a cushioned sole and effortless slip-on fit that works for parties, brunch, or vacation strolls.
Fit & Features
- Square toe
- Multiple rhinestone criss-cross strap design
- Flat sole
- Cushioned footbed
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-000001
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: SILVER
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Chic Steps Braided Block Heels
The heels that instantly elevate every outfit. These block heels feature braided straps and a sleek block heel for a polished look that’s chic for brunch, showers, and dressy occasions.
Fit & Features
- Block heel
- Square toe
- Braided straps
- Adjustable ankle strap with buckle closure
- Cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-000333
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: WHITE
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Pretty Petals Flower Hair Claw Clip Set
Cute hair day incoming. This flower hair claw clip set makes styling feel effortless with playful petal designs that add a soft, fun finish to any look.
Fit & Features
- Three-pack hair claw clip set
- Varying-sized flower designs
Style Number/Barcode: 07006-000138
Category Name: Vacation Looks
Price: $11.90
Availability: Out of Stock
Product Badge:- Ships Free
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Styled And Booked Halter Top
This top is what you throw on when the plan is “look cute, no stress.” This paisley halter top drapes effortlessly with a tie front and flowy fit—perfect with denim when you want that styled but chill vibe.
Fit & Features
- Paisley print, woven fabric
- Halter neckline with tie front
- Open back with stretchy smocked panel
- Flowy flyaway crop silhouette
- Runs true to size
Style Number/Barcode: 06003-000278
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Sunkissed Siren Beaded Abstract Print Bikini Bottoms
Soft glow, sun-kissed skin, and these bikini bottoms doing all the talking. The abstract print and beaded details give you that effortlessly styled look that feels just as good lounging poolside as it does layered under denim. Style with the matching bikini top.
Shop Matching Top: Sunkissed Siren Beaded Abstract Print Bikini Top
Fit & Features
- Knit fabric, high stretch
- Abstract print
- Beaded accents
- Tie-side closures
- Cheeky fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000026
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: MULTI
Available Size: S, M, L
Product Badge:- Part of a Set
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Sunkissed Siren Beaded Abstract Print Bikini Top
Soft glow, sun-kissed skin, and this bikini top doing all the talking. The abstract print and beaded details give you that effortlessly styled look that feels just as good lounging poolside as it does layered under denim. Style with the matching bikini bottoms.
Shop Matching Bottoms: Sunkissed Siren Beaded Abstract Print Bikini Bottoms
Fit & Features
- Knit fabric, high stretch
- Abstract print
- Triangle design, center turquoise-embellished oval-shaped accent
- Halter tie-back spaghetti straps, beaded accents
- Lower tie-back spaghetti straps
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 07104-000018
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: MULTI
Available Size: S, M, L
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Double Take Floral Chiffon Ruffle Maxi Dress
Cue the double takes. This floral chiffon maxi dress brings the drama with ruffles, cutouts, a flirty slit, and breezy movement that shows up beautifully everywhere from brunch plans to sunset parties.
Fit & Features
- Sheer chiffon fabric with full-length stretchy knit lining
- Sleeveless sweetheart neckline, no-slip strip, padded bust, knotted center
- Halter tie-back straps, stretchy smocked back
- Asymmetric side cutouts leading to an open lower back
- Ruffled design, high-cut front slit
- Maxi-length flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-000888
Category Name: Vacation Looks
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Minimal Muse Bodycon Midi Dress
Your new go-to dress when the vibe is effortlessly polished. This bodycon midi dress hugs in all the right places while the side slit offers effortless allure for brunch plans, vacations, or sunset cocktails.
Fit & Features
- Sweater knit fabric
- Scoop neckline
- Adjustable spaghetti straps
- Side slit
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000349
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: TAUPE, ORANGE, MAGENTA
Available Size: S, M, L
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Bold Allure Abstract Animal Print Mini Skort
Not here to blend in—this one sets the tone. This abstract animal print mini skort hugs just right with a mid-rise waist, tiered ruffled design, and airy mesh feel that keeps things bold but effortless. Style with the matching halter top.
Shop Matching Top: Bold Allure Abstract Animal Print Halter Top
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Abstract animal print
- Mid-rise waist
- Tiered ruffled design, mini-length overlay, A-line fit
- Tie detail, short side slit
- Hidden fitted knit shorts
- Runs true to size
Style Number/Barcode: 06503-000237
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: S, L
Product Badge:- Part of a Set
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City Walk Tortoise Oversized Sunglasses
Put these on, and suddenly your outfit feels more put-together. These oversized tortoise sunglasses bring that effortless polish with a bold frame that works from coffee runs to weekend plans.
Fit & Features
- Tinted lenses
- Oversized sunglasses silhouette
- Square shape with rounded edges
- Tortoise pattern
Style Number/Barcode: 07008-000168
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Love The Drama Oversized Sunglasses
A little mysterious, a little extra—in the best way. These oversized sunglasses give instant polish with a bold shape that pulls your whole look together, even on your most off-duty days.
Fit & Features
- Tinted lenses
- Oversized sunglasses silhouette
- Rounded square shape
Style Number/Barcode: 07008-000174
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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It Girl Energy Rimless Shield Sunglasses
These are giving instant main character. The rimless shield design with that warm tinted lens hits different—sleek, bold, and a little futuristic. Perfect for when your outfit needs that extra edge without trying too hard.
Fit & Features
- Rimless shield sunglasses design
- Tinted lenses with warm tone finish
- Rubber nose supports
- Lightweight metal frame construction
Style Number/Barcode: 07008-000178
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Little Plans Eyelet Ruffle Romper
Cute plans call for something this good. This eyelet romper features delicate straps, a softly ruched bodice, and a flirty tiered skirt that gives you the look of a mini dress with the comfort of built-in shorts.
Fit & Features
- Eyelet fabric
- V-neckline with adjustable spaghetti straps
- Ruched fitted bodice
- Tiered flowy skirt with built-in shorts
- Runs true to size
Style Number/Barcode: 06503-000248
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
Product Badge:- Best Seller
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Sweet Babe Floral Skater Mini Dress
This dress feels like a soft summer day. The airy chiffon, delicate floral print, and flirty tiered skirt give it that effortless romantic vibe. Finished with a lace-up back for a little extra charm at parties, brunch, or any dressy occasion.
Fit & Features
- Floral print chiffon-lined fabric
- Sweetheart neckline, twist bust
- Spaghetti straps that shape the lace-up back
- Skater silhouette
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000866
Category Name: Vacation Looks
Price: $19.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: YELLOW
Available Size: L
Product Badge:- Sale
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Ocean Daydream Seashell Mini Dress
Catch flights or just compliments in this mini dres that hugs just right with delicate shell details and a breezy open back made for sunny getaways and golden hour dinners.
Fit & Features
- Crochet knit-lined fabric with seashell embellishments
- V-neckline
- Spaghetti straps shape the lace-up back design
- Bodycon fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000536
Category Name: Vacation Looks
Price: $52.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
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Paradise Ready Floral Maxi Dress
Unlock vacation energy in this floral maxi dress perfect for cocktail dinners, sunset strolls, and looking chic on the beach! This dress is designed in a flattering mermaid fit with a flared hem that brings effortless drama to every step.
Fit & Features
- Statement tropical floral print
- Mesh fabric lined with soft knit
- Tube strapless neckline
- Mermaid fit
- Flared maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001141
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L, XL