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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Always Alluring Halter Crop Top
Entice them all with your alluring look in this bold halter crop top! It features a high halter neckline, spaghetti straps that lead to a cross-back lace-up design, a fitted, cropped hem, and spaghetti straps at the waist that tie in the back. The textured knit fabric offers plenty of stretch. Style this chic top with the matching wide-leg pants!
Shop Matching Bottoms: Always Alluring Wide-Leg Pants
Fit & Features
- Sleeveless halter neckline
- Spaghetti straps, cross-back lace-up design, tie closure
- Fitted, cropped hem
- Waist spaghetti straps, tie-back closure
- Textured knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4694
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bri High-Rise Split Hem Flare Jeans by Windsor Denim
Elevate your everyday outfits with a fab retro vibe with the Bri split hem flare jeans by Windsor Denim. They feature a high-rise waist, a hip-hugging fit that continues throughout the legs, and a flared hem with a front split hem accent. Style with a crop top and platform heels.
Fit & Features
- High-rise waist
- Hip-hugging fit
- Form-hugging fit throughout the legs
- Flared hem, front split hem
- Front button closure, five-pocket and belt loop design
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06602-0405
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Effortless Style Sleeveless Romper
Get that effortless style that's perf for warmer months in this casual and cute sleeveless romper. It features tank shoulder straps, a deep V-neck and back, a high waist with smocked detailing, trendy side cutouts, and flowy shorts. Pair this gauze romper with strappy sandals and hoop earrings.
Fit & Features
- Tank shoulder straps
- Deep V-neck and back
- High waist, smocked detailing
- Side cutouts
- Flowy shorts
- Gauze fabric
- Runs true to size
Style Number/Barcode: 06303-0221
Category Name: Vacation Looks
Price: $14.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Spring Style Floral Romper
Show off an effortless spring style with this adorable chiffon romper. It features short puff sleeves, a subtle sweetheart neckline with a ruched bust, a smocked back design, dual high waist seams, and flowy shorts with a cute fit and flare silhouette. The airy chiffon fabric features a dainty floral print pattern. Complete the look with braided sandals.
Fit & Features
- Short puff sleeves, elastic cinched hems
- Sweetheart neckline, ruched bust
- Smocked back design
- Dual high waist seams, flowy shorts, fit and flare silhouette
- Dainty floral print
- Sheer chiffon fabric, partial knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0251
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Gal Floral Boho Flare Pants
You'll be the trendiest gal at the festival or concert in these boho flare pants! They feature a flattering high-rise elastic waist, a hip-hugging fit, and a flared hem. The pants are designed with a floral striped print on stretchy brushed knit fabric. Complete the look in a crochet top and a hat.
Fit & Features
- High-rise elastic waist
- Hip-hugging fit
- Flared hem
- Floral striped print
- Brushed knit stretchy fabric
- Runs true to size
Style Number/Barcode: 06502-0910
Category Name: Vacation Looks
Price: $11.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In For Romance Short Skater Dress
You'll be in for the romantic vibes of this short skater dress perfect for bridal showers or day dates! It features three-quarter-length puff sleeves, a sweetheart neck, a tie-front, and a fit and flare silhouette. The dress is composed of a swiss dot pattern cotton fabric with a smooth woven lining. Complete the look in simple block heels.
Fit & Features
- Three-quarter-length puff sleeves
- Square neck, tie-front
- Skater silhouette
- Short-length hem
- Swiss dot pattern, smooth woven lining
- No stretch
- Runs true to size
Style Number/Barcode: 05102-4902
Category Name: Vacation Looks
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild Blooms Floral Short Dress
Tame your wild side and showcase this flirtatious floral short dress perfect for a casual picnic date! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, and a cutout back accent. Complete the look in wedges.
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Bodycon silhouette
- Cutout back accent
- Short-length hem
- Floral print knit fabric, knit lining at the bust, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4579
Category Name: Vacation Looks
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring In Full Swing Floral Skater Dress
With spring in full swing, this floral skater dress is an adorable must-have for the season! It features a V-neckline and a matching V-back design with a tie closure, sheer long balloon sleeves, dual high waist seams, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The airy chiffon fabric features a blooming floral print pattern. Style with strappy mules for weekend brunch!
Fit & Features
- V-neckline, V-back design, tie closure
- Sheer long balloon sleeves, elastic cinched hems
- Dual high waist seams, smocked back
- Short skater skirt, tiered ruffled design
- Fit and flare silhouette
- Floral print, sheer chiffon fabric, partial woven lining
- Runs true to size
Style Number/Barcode: 05101-2140
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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That 70s Chick Retro Print Mini Dress
Inspired by the groovy era, you'll look like a cute chick in this retro mini dress perfect for parties! It features a sleeveless square neck, spaghetti straps, side ruched seams that hug your figure, a bodycon silhouette, and a geometric-retro print design. Complete the look with bold earrings.
Fit & Features
- Sleeveless square neck, spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Geometric-retro print
- Knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5005
Category Name: Vacation Looks
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Gorgeous Blooms Puff Sleeve Crop Top
Dress up your weekend brunch 'fits with this gorgeous blooming floral crop top. It features short puff sleeves, a subtle sweetheart neckline, front hook-eye closure, trendy lattice side detailing, and a cropped hem. Style with a form-hugging mini skirt and mules.
Fit & Features
- Short puff sleeves, elasticized hems
- Sweetheart neckline
- Flexible boning, front hook-eye closures
- Stretchy side lattice straps
- Cropped hem
- Floral print pattern
- Smooth woven fabric, lined, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1864
Category Name: Vacation Looks
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flirty Ways Halter Lace Trim Crop Top
With this flirty crop top for celebrations or date night, you'll stun in the plunge halter V-neckline with a dainty lace trim and partially open back. Pair with the matching skirt to complete the look.
Shop Matching Bottoms: Flirty Ways Ruched High Slit Midi Skirt
Fit & Features
- Double-lined stretchy knit fabric
- Plunge halter V-neckline, lace trim, tie closure
- Partially open back
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06001-000094
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sporty Babe Skater Skort
Channel a sporty babe vibe with this adorable skater skort! It features a high-rise waist with a flattering V-shaped design, fitted shorts, and a short skater skirt overlay. The smooth jersey knit fabric offers plenty of stretch. Style with a crop top and sneakers.
Fit & Features
- High-rise waist, V-shaped design
- Fitted shorts
- Short skater skirt overlay
- Jersey knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06503-1065
Category Name: Vacation Looks
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cabo Calling Boho Tulip Pants
Answer the call! Look fab on vacay in this boho tube top featuring an eye-catching tie-front, halter neckline, a smocked back, and a cute boho-inspired print on lined woven fabric with no stretch. Complete the look in matching pants and sandals.
Shop The Matching Top: Cabo Calling Boho Tube Top
Fit & Features
- Elasticized high-rise waist
- Front tulip-cut slits
- Boho-inspired print
- Woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06302-0616
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cabo Calling Boho Tube Top
Answer the call! Look fab on vacay in this boho tube top featuring an eye-catching tie-front, halter neckline, a smocked back, and a cute boho-inspired print on lined woven fabric with no stretch. Complete the look in matching pants and sandals.
Shop The Matching Pants: Cabo Calling Boho Tulip Pants
Fit & Features
- Sleeveless, halter neckline
- Tie-front design
- Ultra cropped hem
- Smocked back
- Boho-inspired print
- Woven lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 06003-1581
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gorgeous Blooms Sleeveless Crop Top
Style up your summer date looks with this gorgeous blooming floral crop top. It features adjustable spaghetti straps, a sweetheart neckline, a underwire bust, front hook-eye closures, and a cropped fit. Complete the outfit with a mini skirt and your favorite heels.
Fit & Features
- Adjustable spaghetti straps
- Sleeveless sweetheart neckline
- Underwire bust, hook-eye closures
- Smocked back
- Cropped hem
- Floral print pattern
- Woven lined fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1863
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feeling Playful In Floral Babydoll Dress
You'll be feeling playful in this floral babydoll dress perfect for bridal showers or dressy weekend brunches! It features a sleeveless square neck, adjustable spaghetti straps, an empire seam, and a flared short-length hem. The dress is designed with flower appliques on airy chiffon fabric with a woven lining. Complete the look in cute wedges.
Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Empire seam, babydoll silhouette
- Flared, short-length hem
- Flower appliques, chiffon fabric, woven lining
- Runs true to size
Style Number/Barcode: 05101-2470
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Captivate In Floral Strapless Dress
Captivate the crowd in this floral strapless dress at brunches or parties! It features non-slip grip lining along the neckline, side ruched seams that hug your curves along the bodycon silhouette, and a mini-length hem. The dress is designed with a watercolor floral print on mesh fabric with a stretchy knit lining. Complete the look in metallic block heels.
Fit & Features
- Strapless neckline, non-slip grip lining
- Back zipper and hook-eye closure
- Side ruched seams
- Bodycon silhouette, mini-length hem
- Watercolor floral print
- Mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2271
Category Name: Vacation Looks
Price: $5.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Spring Vibes Floral Skater Dress
This adorable floral skater dress will bring those sweet spring vibes to your look! It features a sweetheart neckline, short puff sleeves, a high waist, a short skater skirt with a ruffled hem, and a fit and flare silhouette. The lightweight chiffon fabric features a dainty floral print pattern. Style with strappy sandals.
Fit & Features
- Sweetheart neckline, short puff sleeves, elastic cinched hems
- High waist seam, smocked back design
- Short skater skirt, ruffled hem
- Fit and flare silhouette
- Small floral print
- Chiffon fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-2080
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Golden Hour Floral Ruffled Skater Dress
Snap a dreamy pic for golden hour in this floral skater dress and watch the likes come through! It features an off-the-shoulder, sweetheart neckline with ruffle trim, peasant long sleeves, a smocked bodice with a front adjustable drawstring, a cutout waist, and a flowy tiered ruffled short-length hem. Complete the look in chic clear strap mules.
Fit & Features
- Off-the-shoulder, sweetheart neck, ruffle trim
- Peasant long sleeves
- Smocked bodice, front adjustable drawstring
- Cutout waist, skater silhouette
- Tiered ruffle short hem
- Watercolor floral print, non-stretch woven fabric
- Runs true to size
Style Number/Barcode: 05101-1987
Category Name: Vacation Looks
Price: $5.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bright As Day Platform Block Heel Sandals
Today's forecast calls for these bright and cheery platform sandals perfect for a beach day or daytime party! They feature an almond toe, wide clear PVC strap, and lucite low block heel, and are composed of faux leather material. Complete the look with cute sunglasses.
Fit & Features
- Almond toe
- Wide clear PVC strap
- Lucite low-block heel
- Platform sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4202
Category Name: Vacation Looks
Price: $12.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Artsy Cute Geo Print Chain Strap Dress
Express your artsy side in this cute mini dress perfect for parties and a vacation look! The sleeveless dress features eye-catching chain straps, a sweetheart neck, a bodycon silhouette, side ruched seams, and a trendy geometric print on mesh fabric. Style with a choker and platform heels.
Fit & Features
- Sleeveless sweetheart neckline
- Chain straps
- Bodycon silhouette
- Side ruched seams
- Mini-length hem
- Geometric print, mesh fabric
- Runs true to size
Style Number/Barcode: 05103-4911
Category Name: Vacation Looks
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Paradise Bound Tropical Print Crop Top
Jet set off to paradise with this fabulous crop top packed in your carry-on! It features a sleeveless square neckline, bungee spaghetti straps, ruched side seams, a fitted, cropped hem, and a tropical palm leaf print that radiates vacay vibes. Style with the matching mini skirt!
Shop Matching Bottoms: Paradise Bound Tropical Print Mini Skirt
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Ruched side seams
- Fitted, cropped hem
- Tropical palm leaf print
- Mesh fabric
- Runs true to size
Style Number/Barcode: 06001-4751
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Paradise Bound Tropical Print Mini Skirt
Jet set off to paradise with this fabulous mini skirt packed in your carry-on! It features a high-rise waist, ruched side seams, a mini-length hem, a curve-hugging fit, and a tropical palm leaf print that radiates vacay vibes. Style with the matching crop top!
Shop Matching Top: Paradise Bound Tropical Print Crop Top
Fit & Features
- High-rise waist
- Ruched side seams
- Mini-length hem
- Form-hugging silhouette
- Tropical palm leaf print
- Mesh fabric
- Runs true to size
Style Number/Barcode: 06501-0803
Category Name: Vacation Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Plunging Into Basics Surplice Jumpsuit
Take the plunge into a basic jumpsuit that keeps it part casual, part stylish. The jumpsuit features a sleeveless wrap V-neckline with spaghetti straps, an elastic waistband, hidden side pockets, and a straight leg fit with an elastic hem. The jumpsuit is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete the look with mules and statement earrings.
Fit & Features
- Sleeveless wrap V-neckline
- Spaghetti straps
- Elastic waistband
- Hidden side pockets
- Straight leg fit with elastic hem
- Lightweight woven fabric, relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06302-0729
Category Name: Vacation Looks
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free