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.

  • Time To Drink Tequila Graphic Tee

    Get ready to go to happy hour with your squad in the cutest graphic tee! It features a crew neckline with a side cutout, short sleeves, a front agave and limes graphic with the script "Time To Drink Tequila," a mid-length hem, and a relaxed fit. The cotton fabric offers a moderate stretch. Style with denim shorts and strappy sandals.

    Fit & Features

    • Crew neckline, side cutout
    • Short sleeves
    • Agave and limes graphic
    • Script that reads, "Time To Drink Tequila"
    • Mid-length hem, relaxed fit
    • Cotton fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1558

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay On My Mind Floral Mini Skirt

    You'll be ready for your vacay getaway with this bold floral mini skirt. It features a high-rise waist, dual vertical seams down the front, all-over ruching, a mini-length hem, and a curve-hugging silhouette. The lined mesh fabric features a tropical floral print pattern. Style with the matching bustier and a pair of mules!

    Shop Matching Top: Vacay On My Mind Floral Bustier Top

    Fit & Features

    • High-rise elasticized waist, back zipper, hook and eye closure
    • Dual vertical seams down the front
    • All-over ruching
    • Mini-length hem, bodycon fit
    • Tropical floral print
    • Sheer mesh fabric, full knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0791

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacay On My Mind Floral Bustier Top

    You'll be ready for your vacay getaway with this bold floral bustier top. It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a corset-designed bodice with ruching at the bust, and a fitted, cropped hem. The mesh fabric features a tropical floral print pattern. Style with the matching mini skirt and a pair of mules!

    Shop Matching Bottoms: Vacay On My Mind Floral Mini Skirt

    Fit & Features

    • Sleeveless sweetheart neckline, padded cups
    • Adjustable spaghetti straps
    • Corset-designed bodice, ruched bust
    • Fitted, cropped hem
    • Tropical floral print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4714

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Seriously Stylish Satin Trouser Pants

    These satin trouser pants are seriously stylish for working babes and after-hours fun! They feature a flattering high-rise waist, hidden side pockets, and a wide-leg silhouette. Complete the look in a sleeveless top and strappy sandals. 

    Fit & Features

    • High-rise waist
    • Hidden side pockets
    • Side zipper closure
    • Wide-leg silhouette
    • Silky satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06402-1281

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Start Your Engines Slash Graphic Crop Tee

    Start your engines and rev up in edgy style by showcasing this graphic crop tee! It features short sleeves, a crew neck, a front graphic with "Custom Parts Classic Motors" and a slashed cropped hem. Complete the look in trendy denim jeans for a concert or chilling with friends!

    Fit & Features

    • Short sleeves
    • Crew neck
    • Front graphic and script, "Custom Parts Classic Motors"
    • Slashed cropped hem
    • Stretchy cotton fabric
    • Runs true to size

    Style Number/Barcode: 06002-1555

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Beauty Ditsy Floral Romper

    Keep it sweet in this gorg romper that is perf for your next date night! The romper features a sleeveless square neckline, spaghetti straps, a ditsy floral print, a lower back keyhole cutout with tie-back straps, and wide-leg shorts with a tiered skater overlay.  Complete the look with sandals.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ditsy floral print
    • Lower back keyhole cutout, tie-back straps
    • Wide-leg shorts
    • Tiered skater overlay, fit and flare silhouette
    • Woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06403-0276

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Classic Chic Vibes Paperbag Romper

    Bring those classic and chic vibes to your look with this stylish romper! It features a sleeveless V-neckline, adjustable spaghetti straps, a high-rise paperbag waist, a tie-front belt, and a fitted silhouette. Complete the outfit with a layered necklace and heeled mules.

    Fit & Features

    • V-neckline
    • Adjustable spaghetti straps
    • High-rise paperbag waist, tie-front belt
    • Hidden side zipper and hook and eye closure
    • Side pockets
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06303-0218

    Category Name: Vacation Looks

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Go-Getter Gal Zebra Print Wrap Tie Top

    Amp up your business casual fits' or everyday style with this zebra print top to create stylish looks for the girls on the go! The top features peasant long sleeves with dual button cuffs, a V-neckline, surplice bodice with a wrap-tie cropped hem on smooth woven fabric. Complete the look in straight-leg jeans, heels, and a mini tote.

    Fit & Features

    • Peasant long sleeves, dual button cuffs
    • V-neckline
    • Surplice bodice
    • Wrap-tie cropped hem
    • Zebra print
    • Smooth woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1997

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Total Jetsetter Swirl Print Flare Pants

    Whether you're jet-setting to an island resort or road-tripping up to a music festival, these swirl print flare pants are just the ticket to make a stylish entrance! They feature a high-rise waist, hip-hugging fit, and a flared hem on brushed stretchy knit fabric. Complete the look in a cute corset top.

    Fit & Features

    • High-rise waist
    • Hip-hugging fit
    • Flared hem
    • Swirl print
    • Brushed stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-2246

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Delightful Duo Halter Polka Dot Crop Top

    Look and feel so delightful in this polka dot halter crop top for an effortlessly poised look for brunch or parties! Pair with the matching skirt.

    Fit & Features

    • Polka dot print, woven-lined fabric
    • Halter neckline, lace trim, spaghetti strap tie, metal insert
    • Padded bra cups
    • Back zipper and hook-eye closure
    • Flexible boning
    • Fitted crop hem
    • Runs true to size

     

    Shop The Matching Skirt: Delightful Duo Polka Dot Ruffle Skirt

    Style Number/Barcode: 06003-2747

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Weekend Ready High-Rise Denim Mom Shorts

    You'll be ready for casual weekend plans with these trendy denim mom shorts. They feature a super high-rise waist with a front button and hidden zipper closure, rolled hems, and a relaxed fit. The denim fabric offers a rigid fit with no stretch. Style with a graphic tee and sandals.

    Fit & Features

    • Super high-rise waist
    • Front button, hidden zipper closure
    • Five-pocket and belt loop design
    • Rolled hems
    • Relaxed fit
    • Denim fabric, rigid fit, no stretch
    • Runs true to size

    Style Number/Barcode: 06603-0351

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Escape To Paradise Tropical Print Mini Skirt

    Look like you're ready to escape to paradise in this dreamy tropical print mini skirt! It features a high-rise waist, a faux wrap-front design, a mini-length hem, and a curve-hugging silhouette. The tropical palm leaf print will give off those vacay vibes. Style with the matching crop top!

    Shop Matching Top: Escape to Paradise Tropical Print Crop Top

    Fit & Features

    • High-rise waist
    • Faux wrap-front design
    • Mini-length hem, form-hugging fit
    • Tropical palm leaf print
    • Texture knit fabric, partial sewn-in knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0596

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Escape to Paradise Tropical Print Crop Top

    Look like you're ready to escape to paradise in this dreamy tropical print crop top! It features a sleeveless scoop neckline, spaghetti straps, an alluring open back with a strappy cross-back lace-up design, and a fitted cropped hem. The tropical palm leaf print will give off those vacay vibes. Style with the matching mini skirt!

    Shop Matching Bottoms: Escape To Paradise Tropical Print Mini Skirt

    Fit & Features

    • Sleeveless scoop neckline, spaghetti straps
    • Open back, strappy cross-back lace-up design, tie closure
    • Fitted cropped hem
    • Tropical palm leaf print
    • Texture knit fabric, partial sewn-in knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4007

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Meet My Gauze And Crochet Romper

    You see what you like, so go for it in this cute romper! It has a sleeveless V-neckline, adjustable spaghetti straps that create a cross-back design, and a fully lined lace bodice. A sheer crochet panel highlights your waist. Shorts are composed of unlined gauze fabric and offer a flowy fit. Complete the look with sandals and sunglasses for a fab day out.

    Fit & Features

    • Sleeveless V-neckline 
    • Adjustable spaghetti straps, cross at back 
    • Sheer crochet panel at the waist
    • Flowy shorts
    • Gauze knit fabric 
    • Relaxed fit, minimal stretch
    • Runs true to size 

    Style Number/Barcode: 06303-0217

    Category Name: Vacation Looks

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual And Chic Linen Shorts

    Stylishly elevate your weekend look with these casual and chic linen-blend shorts! They feature a high-rise waist, a button-front closure, dual front pockets, pleating, and a fitted silhouette. Complete the outfit with the matching vest and a pair of espadrille sandals for happy hour!

    Shop Matching Top: Casual And Chic Cropped Linen Vest

    Fit & Features

    • High-rise waist
    • Button-front closure, hidden front zipper
    • Dual front pockets
    • Pleating
    • Fitted silhouette
    • Linen-blend fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06303-0212

    Category Name: Vacation Looks

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual And Chic Cropped Linen Vest

    Stylishly elevate your weekend look with this casual and chic linen-blend vest! It features a sleeveless V-neckline, a complete button-down front, and a fitted, cropped hem. Complete the outfit with the matching shorts and a pair of espadrille sandals for happy hour!

    Shop Matching Bottoms: Casual And Chic Linen Shorts

    Fit & Features

    • Sleeveless V-neckline
    • Button-down front
    • Dual faux pocket slits
    • Fitted, cropped hem
    • Linen-blend fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1574

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Skip A Beat Ponte V-Neck Skater Dress

    You'll be dressed to impress in this ponte skater dress as a graduate or bride-to-be! It features a sleeveless V-neckline, spaghetti straps, a flattering fit and flare silhouette, and a short-length hem. Complete the look in chic rhinestone heels.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Back zipper closure
    • Fit and flare, skater silhouette
    • Short-length hem
    • Lined ponte-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2235

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Edged Out Fringe Tie-Front Graphic Top

    Find your edge with this sassy graphic crop top perfect for festivals, concerts, and checking out a carnival! It features short sleeves, fringe trim along the shoulders, and a plunging neckline with a tie-front hem. Complete the look in a denim skort and cowboy boots!

    Fit & Features

    • Short sleeves
    • Fringe trim along the shoulders
    • Plunging neckline
    • Tie-front hem, cropped length 
    • Graphic design
    • Stretchy cotton fabric
    • Runs true to size

    Style Number/Barcode: 06002-1563

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Nights Linen High Slit Midi Skirt

    This effortlessly-chic linen midi skirt was made for summer nights! It features a high waist with a low-cut front design, a side knot detail, a midi-length hem with a sultry high slit to showcase some leg, and a flowy silhouette. The linen-blend fabric has a smooth knit lining. Style with a crop top and sandals.

    Fit & Features

    • High waist, low-cut front design
    • Side knot detail
    • Back zipper, hook and eye closure
    • Midi-length hem, high slit
    • Flowy silhouette
    • Linen-blend fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06301-0150

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Escape With Me Tropical Mini Dress

    Escape to an island getaway with this tropical mini dress perfect for a sunset dinner by the shore! It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a knotted bust accent, and a bodycon silhouette. The smooth lined knit fabric offers a moderate stretch. Complete the look in trendy sandals.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Knotted bust accent
    • Bodycon silhouette, mini-length hem
    • Tropical print
    • Lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5004

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Marvel Lace-Up Mini Dress

    Everyone will marvel at you in this marble print mini dress featuring a sleeveless square neck, spaghetti straps that lace up along the back, and a bodycon silhouette. The mini-length dress is composed of a marble-printed mesh fabric with a stretch knit lining. Complete the look in platform wedges for dinner by the beach!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Lace-up back
    • Bodycon silhouette
    • Mini-length hem
    • Marble print, mesh fabric, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4990

    Category Name: Vacation Looks

    Price: $5.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Garden Strolls Floral Tie-Back Skater Dress

    Your stroll through the garden party will be so sweet in this floral chiffon dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty tie-back design, and a fit-and-flare skater silhouette with a short hem. Complete the look in cute sandals.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Tie-back design
    • Fit and flare, skater silhouette
    • Short-length hem
    • Watercolor floral print
    • Airy chiffon, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4903

    Category Name: Vacation Looks

    Price: $9.97 $41.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance Avenue Floral Crochet Skater Dress

    Stroll hand-in-hand with your lover in this floral crochet dress sure to bring the romance! It features a sleeveless square neck, adjustable spaghetti straps, a flirty tie-back design, a high-waist seam, and a short skater silhouette. Complete your darling look in strappy sandals.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Tie-back design, zipper and hook-eye closure
    • High waist seam, skater silhouette
    • Short-length hem
    • Floral crochet, smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2396

    Category Name: Vacation Looks

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blooming Beauty Floral Print Mesh Maxi Dress

    Let your beauty bloom with a mesh maxi dress that features a sleeveless sweetheart neckline with lace trim, a bodycon-fit silhouette, and a pretty floral print throughout! Complete your date night look with stiletto heels! 

    Fit & Features

    • Sheer mesh fabric with knit lining, plenty of stretch
    • Floral print
    • Sleeveless sweetheart neckline, lace trim
    • Spaghetti straps
    • Bodycon-like fit
    • Long maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3785

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M, L, XL