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 Looks
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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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Carefree Bohemian Chic Cutout Maxi Dress
Channel a carefree vibe with a maxi dress that is so bohemian chic! The dress features a bohemian print, a sleeveless V-neckline, spaghetti straps, dual cutouts at the waist, and a maxi-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit. Complete look with sandals and tassel earrings.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Dual cutouts at the waist
- Knit fabric, bohemian print
- Maxi-length silhouette
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4063
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Dream Lace-Up Maxi Dress
Get carried away in this tropical maxi dress that will have you ready for that cabana life! The dress features a tropical floral print, a sleeveless V-neckline, a double row of spaghetti straps that cross at the back, a lace-up back, and a maxi-length silhouette with a high side slit. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and hoops.
Fit & Features
- Tropical floral print
- Sleeveless V-neckline
- Double-row of spaghetti straps, cross at back
- Lace-up back
- High side slit
- Maxi length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-2104
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Party-Ready Espadrille Wedges
These adorable espadrille wedges are perf for all of your summer parties! They feature an open round toe, wide toe straps in a cute criss-cross design, an adjustable ankle strap, and a trendy espadrille wedge. Style these shoes with your fave floral dress.
Fit & Features
- Open round toe
- Wide toe straps, criss-cross design
- Adjustable ankle strap, buckle detail
- Espadrille wedge
- Runs true to size
Style Number/Barcode: 07406-0256
Category Name: Vacation Looks
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sparkle And Shine Rhinestone Sandals
Bring the shine with sandals that add that luxe glow to your look! The sandals feature an open back, an adjustable rhinestone embellished ankle strap, an open almond toe with a rhinestone embellished strap, and a flat sole. Complete look with a crop top and mini skirt set.
Fit & Features
- Open back
- Adjustable rhinestone ankle strap
- Open almond toe
- Rhinestone strap over the toe
- Flat footbed
- Runs true to size
Style Number/Barcode: 07404-0913
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glam Moment Geometric Clutch
Create a glam moment with a trendy clutch! The clutch features a wooden frame at the top and a triangular-shaped body with a geometric design. Complete look with a skater dress and mules.
Fit & Features
- Wooden frame
- Triangular-shaped body
- Geometric design
Style Number/Barcode: 07203-0712
Category Name: Vacation Looks
Price: $14.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Vibes Floppy Hat
Accessorize your vacay outfits with this on-trend straw hat for laid-back, chic vibes! It features a rounded top and a wide floppy brim with a black trim. Complete your looks with cute oversized sunglasses.
Fit & Features
- Rounded top
- Wide floppy brim, black trim
- Straw material
Style Number/Barcode: 07302-0349
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Diva Oversized Cat Eye Sunglasses
Stay on trend like a true diva with these stylish sunglasses! The sunglasses feature an oversized cat-eye-shaped frame, dark tinted lenses, and a metal bridge, and sleek arms. Complete look with a romper and sandals.
Fit & Features
- Cat-eye shaped frame
- Dark tinted lenses
- Metal bridge
- Sleek arms
Style Number/Barcode: 07008-0880
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Making Trends Geometric Sunglasses
Make a trendy statement in cute sunglasses that complete your look! The sunglasses feature a geometric-shaped frame, metal bridge, nose pads, and sleek arms. Complete look with a romper and sandals.
Fit & Features
- Geometric shaped frame
- Metal bridge
- Nose pads
- Sleek arms
Style Number/Barcode: 07008-0885
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Desire Layered Shorts
Show off your desire for florals in cute shorts! The shorts feature a ditsy floral print, a high-rise elastic waist, a skirt overlay, and a wide-leg hem. The shorts are composed of a lightweight gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with the matching tie front top.
Shop Matching Crop Top: Floral Desire Tie Front Crop Top
Fit & Features
- Ditsy floral print
- Elastic high rise waist
- Skirt overlay
- Wide leg hem
- Gauze knit fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06303-0120
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Desire Tie-Front Crop Top
Show off your desire for florals in a stunning crop top! The top features a ditsy floral print, a plunging V-neckline, a tie-front accent, long sleeves, and a cropped hem. The top is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with the matching shorts.
Shop Matching Shorts: Floral Desire Layered Shorts
Fit & Features
- Ditsy floral print
- Plunging V-neckline
- Tie front
- Long sleeves, elastic cinched hems
- Cropped hem
- Gauze knit fabric, relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-0980
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dainty And Stunning Rhinestone Earring Set
Elevate your casual looks with this dainty and stunning earring set! It features four earrings, including a small rhinestone embellished huggie, a small thin hoop with a rhinestone adorned star charm, a chic rhinestone embellished ear crawler with a drop design, and a sleek double-banded ear cuff. Style this set with a layered necklace.
Fit & Features
- Four-pack earring set
- Small rhinestone embellished huggie, post back closure
- Small thin hoop, rhinestone embellished star charm, post back closure
- Rhinestone embellished ear crawler, drop design
- Double-banded ear cuff
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0869
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Daring Diva Denim Slides
Slip on these trendy denim sandals for a daring and stylish look! They feature an open square toe, a wide toe strap with a center cutout accented with U-shaped buckles, and a flat sole. Pair these slides with a casual dress and cute sunnies.
Fit & Features
- Open square toe
- Wide toe strap
- Center cutout, U-shaped buckle details
- Flat sole
- Denim material
- Runs true to size
Style Number/Barcode: 07404-0771
Category Name: Vacation Looks
Price: $7.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All Day Vibe Mid-Rise Denim Capri Pants
Elevate your casual style in these denim capri pants, perfect for any adventure! The flattering mid-rise waist sits perfectly on your hips, while the form-hugging fit showcases your silhouette with front seam detailing that creates a leg-lengthening effect.
Fit & Features
- Dark wash denim fabric
- Mid-rise waist
- Front seam detailing, form-hugging fit
- Capri-length hem
- Front button closure, belt loop accents
- Back pockets
- Runs true to size
Style Number/Barcode: 06602-0563
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In The Clear Criss-Cross Strap Sandals
Keep it stylish with clear sandals that are totally on trend, bby! The sandals feature an open back, clear criss-cross straps, an open almond toe, and a nailhead trim at the sole. Complete look with a romper and hoops.
Fit & Features
- Open back
- Clear criss-cross straps
- Open almond toe
- Nailhead trim
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-0756
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sparkle And Go Rhinestone Ruffle Sandals
Get ready to sparkle, babe! These luxe sandals feature an easy slip-on design, an open square toe, and a ruffled strap embellished with rhinestones. Complete look with a black mini dress and rhinestone hoops.
Fit & Features
- Slip-on design
- Open square toe
- Ruffled strap over toe
- Rhinestones
- Runs true to size
Style Number/Barcode: 07404-0895
Category Name: Vacation Looks
Price: $7.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wrapped In Style Faux Leather Strappy Sandals
Wrap yourself in these fab sandals to create an effortlessly stunning look! The sandals feature an adjustable ankle strap, a multi criss-cross strap design, and an open almond toe. Complete look with a tie-front top and shorts for a casual day out!
Fit & Features
- Adjustable ankle strap
- Multi criss-cross strap design
- Open almond toe
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-0951
Category Name: Vacation Looks
Price: $7.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summertime Sparkle Rhinestone Sandals
Bring the sparkle to your fab summertime outfits with these glitzy sandals! They feature a slide-on design with an open round toe, a wide rhinestone adorned strap, a flat sole, and a pretty rhinestone trim. Style these sandals with a cute crop top and denim shorts.
Fit & Features
- Slide-on design
- Open round toe
- Wide toe strap, rhinestone embellishment
- Flat sole
- Rhinestone trim
- Runs true to size
Style Number/Barcode: 07404-0925
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sassy Vibes Lace-Up Sandals
Bring the sassy vibes to your summertime look with these trendy sandals! They feature an open round toe with thin straps, a fab lace-up design that ties at the back, and a flat sole. The faux leather material has an all-over snake print. Style these sandals with a basic tee and denim shorts.
Fit & Features
- Open round toe, thin straps
- Lace-up design, ties at the back
- Flat sole
- Faux leather material, snake print
- Runs true to size
Style Number/Barcode: 07404-0953
Category Name: Vacation Looks
Price: $7.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Glam Rhinestone Sandals
Get an everyday glam vibe with these fab sandals! They feature an open square toe, a toe strap with rhinestone embellishment, a metallic adjustable ankle strap, a flat sole, and a pretty rhinestone trim. Style these sandals with a casual dress and cute sunnies.
Fit & Features
- Open square toe
- Toe strap, rhinestone embellishment
- Metallic adjustable ankle strap
- Flat sole
- Rhinestone trim
- Runs true to size
Style Number/Barcode: 07404-0933
Category Name: Vacation Looks
Price: $12.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Totally Chic Tie Dye Tie Front Top
Channel those chic carefree vibes with a cute tie front top! The top features a tie-dye print, long sleeves, a tie-front accent, and a cropped hem. The top is composed of sheer lightweight woven fabric that offers a relaxed fit. Complete look with high waist shorts and mules.
Fit & Features
- Tie-dye print
- Plunging V-neckline
- Tie-front
- Long sleeves
- Cropped hem
- Lightweight woven fabric
- Relaxed fit, runs true to size
Style Number/Barcode: 06204-0910
Category Name: Vacation Looks
Price: $8.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fierce Vibes Cutout Mini Dress
Bring the fierce vibes to your look with this bold leopard print mini dress! It features a sleeveless V-neckline, spaghetti straps, sultry dual waist cutouts, and a short, curve-hugging silhouette. Style this dress with strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Dual waist cutouts
- Mini-length, form-hugging fit
- Brushed knit fabric, moderate stretch
- Leopard print
- Runs true to size
Style Number/Barcode: 05103-4017
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet And Flirty Chiffon Mini Dress
Sweet and flirty, this airy chiffon dress is perf for summer. It features a sleeveless V-neckline, adjustable spaghetti straps that lead to a cross-back design, ruffled seam detailing, and a short, flowy silhouette. Complete the look with chic mules.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross-back design
- Hidden back zipper and hook and eye closure
- Ruffled seam detailing
- Mini-length, flowy silhouette
- Sheer chiffon fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-1106
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Raise The Stakes High Slit Cutout Dress
Raise the stakes in a bold maxi dress that dares to stun! The dress features a sleeveless halter neck with a racer bust, a sexy cutout at the midriff, ruching at the waist, and a high-side slit. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with hoops.
Fit & Features
- Halter neck with racer bust
- Cutout at the midriff
- Ruching at waist
- High side slit
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4108
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Boho Babe Lace Tie-Front Top
Layer on this effortlessly chic lace top to look like a total boho babe! It features long bishop sleeves, a V-neckline, a tie-front detail, and a cropped, relaxed fit. Style this top over a casual dress for a lightweight summer layer.
Fit & Features
- Long bishop sleeves, elastic cinched hems
- V-neckline
- Tie-front
- Cropped, relaxed fit
- Sheer lace fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-0978
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale