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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Spring Picnic Lace-Up Espadrille Wedges
The perfect espadrille wedges for having the cutest picnic fit! They feature an almond toe, platform sole, and faux leather lace-up straps. Complete the look in a flirty skater dress.
Fit & Features
- Almond toe
- Platform espadrille sole
- Wedge style
- Faux leather lace-up straps
- Runs true to size
Style Number/Barcode: 07406-0298
Category Name: Vacation Looks
Price: $12.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spring Things Lace-Up Espadrille Wedges
Embrace all things spring! Sunnier days are ahead and these chic wedges are every girl's staple for creating fresh looks. They feature an almond toe, espadrille platform sole, and faux leather lace-up straps. Complete the look in a flowy sundress.
Fit & Features
- Almond toe
- Espadrille platform sole
- Wedge style
- Faux leather lace-up straps
- Runs true to size
Style Number/Barcode: 07406-0299
Category Name: Vacation Looks
Price: $12.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Tropic Strappy Back Midi Dress
Flaunt your figure on vacay girl! This floral tropic midi dress is perfect for a dinner with a view. Featuring a sleeveless V-neckline, spaghetti straps, a strappy open-back, a bodycon silhouette, and an asymmetrical hem. Complete the look in chic wedges.
Fit & Features
- Sleeveless, V-neck, spaghetti straps
- Strappy open-back, tie closure
- Bodycon silhouette
- Asymmetrical midi-length hem
- Floral tropic print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4376
Category Name: Vacation Looks
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Laced in Daydreams Satin Halter Floral Mini Dress
This floral satin halter mini dress is sweet, flirty, and made for RSVP-ing yes, complete with dreamy lace details and a flattering A-line silhouette.
Fit & Features
- Floral print, woven satin fabric, bust lining
- Lace trim halter neckline, spaghetti strap tie
- A-line silhouette
- Lace trim front slit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000652
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cool Vibes Border Print Flare Pants
Effortlessly cool vibes all around! Style these flare pants for the perf desert festival fit. They feature a high-rise elasticized waist, form-fitting silhouette, and a flared hem on paisley border print knit fabric. Complete the look in a basic crop cami.
Fit & Features
- High-rise elasticized waistband
- Form-fitting silhouette
- Flared hem
- Paisley border print
- Stretch knit fabric
- Fits true to size
Style Number/Barcode: 06502-0871
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Festive Medallion Flare Pants
Get ready for the festival season in these boho flare pants featuring a high-rise elasticized waist, form-fitting silhouette, and a unique medallion border print on brushed knit fabric with plenty of stretch. Complete the look in a chic panama hat.
Fit & Features
- High-rise elasticized waist
- Form-fitting silhouette
- Flared hem
- Medallion borderprint
- Brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06502-0851
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Paisley Babe Flare Pants
These paisley flare pants are total babe status! They feature a high-rise elasticized waist and a form-fitting silhouette on brushed knit fabric with a moderate stretch. Complete the look in a flirty tie-front top.
Fit & Features
- High-rise elasticized waist
- Form-fitting silhouette
- Flared hem
- Paisley print
- Brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06502-0844
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Reese High Rise Denim Shorts By Windsor Denim
Laidback and chill, you'll the Reese high-rise denim shorts by Windsor denim! They feature a vintage-inspired silhouette with a trendy roll cuffed hem on medium wash denim fabric. Complete the look in a corset top and sandals.
Fit & Features
- High-rise waist
- Vintage-inspired silhouette
- Roll cuffed hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Medium wash denim fabric, no stretch
- Fits true to size
Style Number/Barcode: 06603-0259
Category Name: Vacation Looks
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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The Cutest Vibe Ditsy Floral Romper
Showcase the cutest vibe this summer season in this ditsy floral printed romper. It features short fitted cap sleeves, a V-neckline, center ruching with an adjustable drawstring, a high waist seam with a front cutout, and flowy shorts. Style this romper with a classic denim jacket and espadrille sandals.
Fit & Features
- Short cap sleeves
- V-neckline
- Center ruched detailing, adjustable drawstring
- High waist seam, front cutout
- Flowy shorts
- Ditsy floral print
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06503-0979
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Swept Away Floral Ruffled Maxi Dress
Get swept up in a pretty maxi dress that brings the romance! The dress features a sleeveless sweetheart neckline, tie-up spaghetti straps, tiered ruffles, a floral print, and a maxi-length silhouette. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with sandals and butterfly earrings.
Fit & Features
- Sleeveless sweetheart neckline
- Tie-up spaghetti straps
- Tiered ruffles
- Floral print
- Maxi length silhouette
- Lined lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-1101
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet And Chic Paper Bag Shorts
Sweet and chic, these dressy paper bag shorts will elevate your everyday looks. They feature a high-rise waist, a tie-front belt, front pockets, and a relaxed fit. Style with a basic bodysuit or a cute cropped blouse.
Fit & Features
- High-rise elasticized paper bag waist
- Tie-front belt
- Front pockets, single faux back pocket
- Relaxed fit
- Woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0204
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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She's Fab Oversized Sunglasses
Keep your summer look on point with these fab oversized shades! The sunglasses feature a square-shaped thin metal frame with cool ombre lenses. Style with a sleek crossbody purse.
Fit & Features
- Square-shaped thin metal frame
- Ombre lenses
- 100% UV protection
Style Number/Barcode: 07008-0955
Category Name: Vacation Looks
Price: $3.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Minimalistic Glam Huggie Three Pack
Love that minimalistic look? Add these glam huggie earrings to your daily lineup. They feature a set of three pairs two with rhinestone insets and post-back closure and one large solid hoop with omega-back closure. Complete the look in a chic casual dress with a blazer.
Fit & Features
- Three pack set
- Two rhinestone small hoops
- Post-back closure
- One large solid hoop
- Omega-back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged
Style Number/Barcode: 07001-1225
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dancing Queen CZ Stone Belly Chain
Dance all night queen! Elevate your swimwear in this belly stone featuring CZ stone charms and an adjustable lobster clasp closure. Complete the look in a boho bikini set.
Fit & Features
- CZ stone charms
- Adjustable lobster clasp closure
- Dainty chain link
Style Number/Barcode: 07002-1203
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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New Frames Cat Eye Sunglasses
Everyone will be checking you in these sunglasses! They feature a sleek metal frame with cat-eye accents, gradient lens, and rubber nose supports for comfortable wear. Complete the look in a trendy sweater dress.
Fit & Features
- Sleek metal frame
- Cat-eye accents
- Gradient lens
- Rubber nose supports
- 100% UV protection
Style Number/Barcode: 07008-0933
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Daydream Layered Charm Anklet
Create a tantalizing look with this layered charm anklet featuring a three-row design with rhinestones and coin charms with a lobster clasp closure. Complete the look in a flowy kimono and mini dress.
Fit & Features
- Three-row design
- Rhinestones and coin charms
- Lobster clasp closure
Style Number/Barcode: 07003-0329
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Set the Bar Linen Cutout Mini Dress
This flare mini dress sets the bar high! Showcase your daring side in this sleeveless dress featuring a plunge v-neck on the front and back, a smocked bodice, and side elasticized bar cutouts that lead to a flirty mini-length hem. Complete the look in wedges and dainty earrings.
Fit & Features
- Sleeveless, dual plunge v-neck
- Smocked bodice
- Side elasticized bar cutouts
- Flare mini-length hem
- Linen gauze fabric
- Runs true to size
Style Number/Barcode: 05102-4831
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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One Take V-Neck Ruffle Skater Romper
One take in this skater romper and you'll be so obsessed! With a flirty tie back design and flattering skater silhouette, this romper will be your favorite style for brunch to parties!
Fit & Features
- Knit fabric, moderate stretch
- Adjustable spaghetti straps
- Ruffle V-neckline
- Tie-back design
- Skater silhouette
- Ruffle layered short-length hem
- Runs true to size
Style Number/Barcode: 06503-1143
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Geneviève Floral Chiffon Wrap Dress
Special Occasion
Wrap yourself in a floral dress that brings romance to your event! Geneviève features a darling floral print, a sleeveless V-neckline, and adjustable spaghetti straps that cross at the back. Her back features a lace-up strap design and an elastic stretch at the lower back that leads to a zipper closure. Her slim-fit waist leads to a flowy wrap silhouette that is accented with a high side slit. She is composed of a lined chiffon fabric that offers a form hugging fit with minimal stretch. Complete look with wedges and a clutch for the perfect wedding guest outfit.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, lace-up back
- Back zipper closure
- Floral print
- Wrap silhouette, high side slit
- Lined chiffon fabric
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 05002-1889
Category Name: Vacation Looks
Price: $19.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Effortless Style Moves Midi Dress
Make effortless style moves in this adorably-chic midi dress. It features a sleeveless square neckline with a ruffled trim, thin ruffled shoulder straps, a stretchy smocked bodice, a high waist, and a flowy, midi-length, A-line silhouette with a front slit. Complete the look with espadrille sandals.
Fit & Features
- Sleeveless square neckline, ruffled trim
- Thin ruffled shoulder straps
- Stretchy smocked bodice
- High waist seam, flowy A-line silhouette
- Midi-length hem, front slit
- Lightweight linen fabric, woven skirt lining
- Runs true to size
Style Number/Barcode: 05102-4347
Category Name: Vacation Looks
Price: $12.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Vibes Ditsy Floral Romper
Bring the sweet vibes to your everyday summer look with this adorable romper. It features a sleeveless square neckline, spaghetti straps, a fitted smocked bodice, flowy shorts, and an all-over ditsy floral print pattern. Style this romper with a jean jacket and slip-on sandals.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Smocked bodice, fitted high waist seam
- Flowy shorts
- Ditsy floral print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-0978
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fresh And Flirty Floral Romper
Get a fresh and flirty summertime look with this adorable floral printed romper. It features a sleeveless V-neckline with a tie-front design, spaghetti straps, a front waist cutout, a fitted high waist seam, and flowy shorts with a cute ruffled hem. Style with a denim jacket and strappy sandals.
Fit & Features
- Sleeveless V-neckline, tie-front
- Spaghetti straps
- Front waist cutout
- Fitted high waist seam
- Flowy shorts, ruffled hem
- Floral print, lightweight gauze fabric, no stretch
- Runs true to size
Style Number/Barcode: 06303-0209
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Social Linen Fringe Mini Skirt
Make the plans. Get trendy with your look in this linen mini skirt featuring a high-rise waist, fringed hem, and a bodycon fit. Complete the look in the matching top.
Shop Matching Top: Social Linen Tie Strap Crop Top
Fit & Features
- High-rise waist
- Back zipper, hook and eye closure
- Fringed hem
- Bodycon fit
- Linen-lined woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06301-0107
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Social Linen Tie Strap Crop Top
Make the plans. Get trendy with your look in this linen tie strap crop top featuring a sleeveless square neckline with adjustable spaghetti straps, fringed crop hem, and a side zipper closure. Complete the look in the matching bottoms.
Shop Matching Bottoms: Social Linen Fringe Mini Skirt
Fit & Features
- Sleeveless, square neck
- Adjustable tie spaghetti straps
- Fringed crop hem, smocked back
- Side zipper closure
- Linen-lined woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1625
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale