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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Sultry Spice Cutout Maxi Dress
Sultry and spicy! Make jaws drop in this sleeveless maxi dress featuring a one-shoulder neckline, waist cutout details and a form-fitting silhouette with a high-cut side slit for a show of skin. Composed of stretchy slinky knit fabric. Finish the look in lucite mules.
Fit & Features
- Sleeveless, one-shoulder neckline
- Waist cutout details
- Form-fitting silhouette
- High-cut side slit
- Maxi-length hem
- Slinky knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4528
Category Name: Vacation Looks
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Take Me On A Getaway Midi Dress
Pack this alluring and chic midi dress for your next weekend getaway. It features a sleeveless halter neckline with thin straps, front ruched detailing with an adjustable drawstring, a bold front waist cutout, and a midi-length, curve-hugging fit with a high side slit. Style this dress with sleek hoop earrings and strappy sandals.
Fit & Features
- Sleeveless halter neckline, thin straps that tie at the back of the neck
- Front ruching, adjustable drawstring
- Front waist cutout
- Midi-length, form-fitting silhouette, side slit
- Ribbed sweater knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1414
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Beachy Vibes Maxi Sweater Dress
Bring the beachy vibes to your summer look with this effortlessly chic maxi sweater dress. It features a sleeveless scoop neckline, spaghetti straps, an open back with a cross-back strap design, and a fitted, maxi-length silhouette with a high side slit. The sweater knit fabric features pretty crochet detailing. Style this dress with sandals.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Open back, cross-back strap design
- Fitted, maxi-length silhouette, side slit
- Sweater knit fabric, crochet detailing, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1421
Category Name: Vacation Looks
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Passport To Paradise Midi Dress
The island may be breathtaking but you'll also be a sultry view in this sleeveless midi dress featuring a square neck, spaghetti straps, a cutout bodice, asymmetrical hem, and a side ruched drawstring that lets you customize the fit. Complete the look in a straw floppy hat.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Cutout bodice
- Side ruched drawstring
- Form-fitting
- Asymmetrical midi hem
- Slinky knit lined fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4620
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Basic Babe Sleeveless Bodycon Slit Mini Dress
A sleeveless knit mini dress boasts a flattering square neckline, a bodycon fit, and a flirty front slit. Perfect for layering or styling alone.
Fit & Features
- Knit fabric, moderate stretch
- Square neckline
- Shoulder straps
- Front slit
- Bodycon mini-length fit
- Runs true to size
Style Number/Barcode: 06005-2002
Category Name: Vacation Looks
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Leafy Greens Ruffle Skater Romper
Wear your greens! Steal the show on vacay in this palm leaf print romper featuring a sleeveless, square neck, spaghetti straps, open back with tie closure, and a ruffled skater-style skirt with shorts lining. Complete the look in strappy heels.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Open back with tie closure
- Ruffled skater-style skirt
- Shorts lining
- Palm leaf print
- Brushed knit lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06503-0992
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sun Dance Paisley Flare Pants
Dance all day in these boho flare pants featuring a high-rise elasticized waist, form-fitting silhouette, and a paisley multi-print design. Complete the look in a wrap crop top.
Fit & Features
- High-rise elasticized waist
- Form-fitting
- Flared hem
- Boho paisley print
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0920
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Beachy-Chic Bodycon Mini Dress
Showcase a beachy-chic vibe in this curve-hugging bodycon mini dress. It features a sleeveless square neckline, spaghetti straps, ruched detailing down the side seams, and a short, form-fitting silhouette. The stretchy brushed knit fabric features an all-over tropical palm leaf print. Style this dress with espadrille sandals.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ruching down the side seams
- Mini-length, form-fitting, bodycon silhouette
- Tropical palm leaf print
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4696
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Flower Lattice Back Dress
Look as pretty as the island flowers in this tropical maxi dress perfect for a luau dinner! It features a sleeveless, square neck, sleek spaghetti straps, an open back with lattice detailing, a sultry side slit, and a curve-hugging silhouette. Complete your vacay look in large hoop earrings.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Open-back, lattice straps
- Side slit, curve-hugging silhouette
- Maxi-length hem
- Tropical floral print, knit fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4506
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Get That Glitzy Glow Bikini Top
Get that glitzy glow for your weekend getaway with this trendy bikini top! It features a basic triangle design with halter spaghetti straps, tie-back straps, and a lurex glitter mesh fabric with sheer mesh inserts. Complete the look with the matching bikini bottoms.
Shop Matching Bottoms: Get That Glitzy Glow Bikini Bottoms
Fit & Features
- Triangle design
- Halter spaghetti straps
- Tie-back spaghetti straps
- Lurex glitter mesh fabric, sheer mesh inserts
- No padding
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0697
Category Name: Vacation Looks
Price: $8.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In Line High Rise Striped Pants
These woven striped pants should be in line with your summer aesthetic! They feature a high-rise waist, side pockets for keeping your hands warm, and a wide-leg silhouette. Complete the look in the matching top.
Shop The Matching Top: In Line Tie-Front Striped Top
Fit & Features
- High-rise waist
- Side pockets
- Wide-leg silhouette
- Striped woven fabric
- Fits true to size
Style Number/Barcode: 06302-0621
Category Name: Vacation Looks
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In Line Tie-Front Striped Top
This woven striped top should be in line with your summer aesthetic! Featuring kimono-style short sleeves, a tie-front design, and a cropped hem. Complete the look in the matching pants.
Shop Matching Bottoms: In Line High Rise Striped Pants
Fit & Features
- Kimono-style short sleeves
- Tie-front design
- Cropped hem
- Striped woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1220
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sassy Retro Cat Eye Sunglasses
Sassy and retro! These oversized sunglasses feature cat-eye sleek metal frames, tinted gradient lenses, rubber most supports, and arms. Complete the look in a printed jumpsuit for a party.
Fit & Features
- Oversized style
- Cat-eye sleek metal frame
- Tinted gradient lenses
- Rubber nose supports and arms
- 100% UV protection
Style Number/Barcode: 07008-0952
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Paradise Ready One-Shoulder Maxi Dress
This gorgeous tropical printed maxi dress will have you looking ready for a vacay off to paradise! It features a sleeveless one-shoulder neckline, a single bungee spaghetti strap, an asymmetrical waist cutout with a chic O-ring accent, and a curve-hugging, floor-length silhouette with a front slit. The stretchy knit fabric features an all-over palm leaf print. Complete your look with slip-on sandals and your fave shades.
Fit & Features
- Sleeveless one-shoulder neckline
- Single bungee spaghetti strap
- Asymmetrical waist cutout, O-ring accent
- Maxi-length hem, form-fitting silhouette, front slit
- Tropical palm leaf print
- Knit fabric, short knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4484
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island Hopping Tropical Maxi Dress
Feel the island breeze in this tropical maxi dress for your next holiday in the sun! It features a sleeveless, halter neck, a sultry cutout bodice that leads to the open tie-back closure, and a flowy maxi hem with a slit. Complete your vacay look with lace-up heels.
Fit & Features
- Sleeveless, halter neck with tie
- Cutout bodice
- Open-back, tie closure
- Side slit
- Flowy maxi silhouette
- Tropical print, woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 05102-4500
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Away On Vacay Tropical Mini Dress
Going away on vacation? This tropical mini dress will definitely get you in the vacay mood! It features a sleeveless, scoop neck, spaghetti straps, a form-hugging silhouette, and a side ruched seam that leads to the asymmetrical slit hem. Complete the look in chic oversized sunnies.
Fit & Features
- Sleeveless, scoop neck
- Spaghetti straps
- Form-hugging silhouette
- Side ruched seam, asymmetrical slit hem
- Mini-length
- Tropical print, sleek knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4682
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Desert Vacay Sleeveless Maxi Dress
Make sure to pack this effortlessly-chic maxi dress in your weekend bag for your desert vacay! It features a sleeveless plunging V-neck and back design, tank shoulder straps, a high-rise banded waist with side cutouts, and a flowy, floor-length silhouette with a front slit to show some leg. Style this dress with espadrille sandals.
Fit & Features
- Sleeveless plunging V-neck and back design
- Tank shoulder straps
- High-rise banded waist, side cutouts
- Maxi-length hem, flowy silhouette
- Front slit
- Woven gauze fabric, pleated detailing, knit skirt lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4504
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Summer Halter Maxi Dress
Sultry for summer. Raise the chicness in this halter maxi dress featuring a sleeveless bodice with tie-closure, o-ring inset, and a cutout accent leading to the bodycon silhouette with an asymmetrical slit hem. Complete your sultry look in espadrille wedges.
Fit & Features
- Sleeveless, halter neck, tie closure
- O-ring inset, cutout accent
- Bodycon silhouette
- Asymmetrical slit
- Maxi-length hem
- Rib-knit fabric, moderate stretch, fits true to size
Style Number/Barcode: 05102-4467
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Effect Abstract Cowl Halter Crop Top
Printed to perfection in a flattering halter silhouette, this crop top boasts a sultry cowl neckline and an open back to show some skin! Pair with the matching pants.
Fit & Features
- Abstract print, stretchy knit fabric
- Cowl halter neckline, tie straps
- Open back
- Fitted crop hem
- Runs true to size
Shop The Matching Pants: Sultry Effect Abstract Wide-Leg Pants
Style Number/Barcode: 06001-000107
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Kaleidoscope Boho Tie-Front Top
Escape the city life for paradise with this boho crop top featuring a sleeveless, sweetheart neck, adjustable spaghetti straps, a tie-front detail, back smocked design, and a kaleidoscope print. Complete the look in the matching skirt.
Shop Matching Skirt: Kaleidoscope Boho Slit Maxi Skirt
Fit & Features
- Sleeveless, sweetheart neck
- Adjustable spaghetti straps
- Tie-front detail
- Back smocked design
- Kaleidoscope boho print
- Runs true to size
Style Number/Barcode: 06003-1556
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Playful Twist Halter Knit Romper
This halter romper comes with a playful twist! Featuring a sleeveless, keyhole halter neckline with cross straps, tie closure, a partial open-back, high-rise waist, and a flowy short hem. Complete the look in chic espadrille wedges.
Fit & Features
- Sleeveless, halter neckline, tie-closure
- Cross front straps, keyhole
- Partial open-back
- Flowy short hem
- Sleek knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06503-0995
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Kaleidoscope Boho Slit Maxi Skirt
Escape the city life for paradise with this boho maxi skirt featuring a high-rise waist, front high-cut slit, and a kaleidoscope print. Complete the look in the matching top.
Shop Matching Top: Kaleidoscope Boho Tie-Front Top
Fit & Features
- High-rise waist
- Front high-cut slit
- Maxi-length hem
- Kaleidoscope boho print
- Runs true to size
Style Number/Barcode: 06301-0103
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Love It Lace-Up Crop Top
You'll love this lace-up crop top that is an elevated version of your fave basic tanks. It features a sleeveless square neckline, spaghetti straps, a lattice-front design, and a cropped, form-hugging fit. Style with high-rise denim and cute mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Lace-up front, tie closure
- Cropped fit
- Woven fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06003-1861
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Effortless And Chic Cropped Blouse
This effortless and chic cropped blouse is a stunning summer staple! It features a sweetheart neckline with a lace-up tie-front design, half-length bishop sleeves, ruched detailing, and a cropped fit. Style with high-rise denim.
Fit & Features
- Sweetheart neckline
- Lace-up tie-front design
- Half-length sheer bishop sleeves, elasticized hems
- Ruching
- Back zipper closure
- Cropped fit
- Sheer woven fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06003-1878
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance