Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

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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.

  • Girly Chic Lace Trim Mini Skort

    Serve all the girly chic vibes in this cute mini skort designed with a drop waist, pleating, and a peeking lace trim.

    Fit & Features

    • Ponte knit fabric, moderate stretch
    • Drop waist design
    • Pleating
    • Mini-length overlay, skater silhouette, sheer lace trim
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000052

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Always Trending Strapless Striped Bodycon Mini Dress

    Trend right in this strapless mini dress featuring a twist sweetheart neckline with a keyhole cutout and a flattering bodycon silhouette. The striped knit material hugs your curves making it perfect for pairing with sneakers or sandals. 

    Fit & Features

    • Striped print, stretchy knit material
    • Strapless sweetheart twist neckline
    • Keyhole cutout
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5824

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic And Sleek Square Strappy Flat Sandals

    Chic and sleek! These flat sandals offer endless styling options with sleek dual straps and a statement square accent, they're perfect for day or night fun.

    Fit & Features

    • Square toe 
    • Dual straps, square accent
    • Flat sole with trim
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-000009

    Category Name: Vacation Looks

    Price: $18.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: 6, 6.5

  • Short But Sweet Gingham Bow Shorts

    Short but super sweet! These gingham shorts are the cherry on top of a perfect sunny day look featuring a flattering high-rise waist and side bow ties.

    Fit & Features

    • Gingham print, cotton woven fabric
    • High-rise elasticized waist
    • Hidden side pockets
    • Side bow ties
    • Fitted hem
    • Runs true to size

    Style Number/Barcode: 06303-000017

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Ready Tropical Knit Halter Crop Top

    This alluring tropical halter crop top will have you ready for a dreamy vacay! The lined stretchy knit fabric features a bold abstract tropical print pattern to catch all the glances on your getaway. The crop top is shaped with a sleeveless halter neckline with a sultry V-shaped cutout, tie-back halter straps, ruched side seams to accentuate your curves, and a form-hugging fit for a snatched look. Style with the matching wide-leg pants and hoop earrings.

    Shop Matching Bottoms: Vacay Ready Tropical Knit Wide-Leg Pants

    Fit & Features

    • Abstract tropical print
    • Stretchy lined knit
    • Halter neckline, V-shaped cutout
    • Tie-back spaghetti straps
    • Ruched side seams
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5210

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy-Chic Shell Thong Strap Sandals

    These beachy-chic shell thong strap sandals are a style staple for your summer vacay! Made with faux leather, they feature an almond toe, a trendy thong strap design with sleek oval-shaped shell accents, thin adjustable ankle and heel straps with a buckle closure, and a flat sole for comfortable wear. Pair with a crochet top and denim shorts! 

    Fit & Features

    • Faux leather upper
    • Almond toe
    • Thong strap design
    • Oval shell accents
    • Adjustable ankle and heel straps with buckle closure
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1208

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chill Vision Small Rectangle Sunglasses

    For the days when you’re chill, but still need to serve a look. These small rectangle sunglasses are the perfect low-key statement for brunch hangs, solo city strolls, or golden hour selfies.

    Fit & Features

    • Small rectangular-shaped design
    • Plastic frame with glossy finish
    • Thin arms
    • Flexible nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000059

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: NS

  • Knit The Beach Striped Strappy Crochet Crop Top

    This striped crochet crop top is all about the beach life! Featuring a square neckline, spaghetti straps, and a strappy open back, this top is perfect for summer fun. Its cropped hem adds a trendy touch. Complete the look in denim shorts.

    Fit & Features

    • Striped pattern, crochet fabric, no stretch
    • Square neckline
    • Spagehtti strap, strappy open back
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-2007

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twist and Slay Crochet Mini Dress

    Serving looks front to back—literally. This crochet mini dress hugs in all the right places with a twist-back moment that’s made to be seen. Perfect for summer parties, day-to-night vibes, or when you just wanna turn heads.

    Fit & Features

    • Sheer crochet knit fabric with lining, moderate stretch
    • Sleeveless scoop neckline
    • Spaghetti straps
    • Dual twist-back strap design
    • Back cutouts
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000046

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: M, L

    Product Badge:
    • Best Seller
  • Girl Next Door Vibes Cropped Tank

    Look like the total girl next door in this basic cropped tank. This staple piece goes with everything from your casual looks or as a layering piece for a dressed-up look. The cropped tank features a sleeveless bodice and bungee spaghetti straps for a secure and comfortable fit. Complete your girl-next-door look with high waist jeans and a pair of sneakers.

    Shop In More Colors: Girl Next Door Cropped Tank

    Fit & Features

    • V-neckline
    • Bungee straps
    • Cropped
    • Knit fabric
    • Form-hugging fit
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4459

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Natural Romancer Crew Neck Lace Mini Dress

    Indulge in the effortless romance of this lace mini dress perfect for bridal showers, rehearsal dinners, and parties! This stunning dress features short sleeves, a flattering crew neckline, and a bodycon silhouette that hugs your curves. The sheer lace fabric exudes romance, while the attached knit slip lining provides comfort and coverage. Complete the look with earrings and strappy sandals.

    Fit & Features

    • Sheer lace fabric with stretch
    • Attached slip knit lining
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5548

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Ease Strapless Boho Print Wide-Leg Jumpsuit

    The perfect strapless boho jumpsuit for every summer adventure that features a stretchy smocked bodice, a braided waist belt, and a flattering wide-leg fit. The sleek knit fabric offers plenty of stretch and a unique boho-print. 

    Fit & Fetaures

    • Boho-print, sleek knit fabric, moderate stretch
    • Strapless neckline
    • Stretchy smocked bodice
    • Braided waist belt
    • Wide-leg fit
    • Jumpsuit has a 12” front rise with a 29.5” inseam
    • Runs true to size

    Style Number/Barcode: 06502-2524

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ibiza Graphic Fishnet Tank Top

    This graphic tank top is destined to be your plus one on vacations! It is designed in sheer fishnet fabric with a trendy graphic and script that reads "Ibiza."

    Fit & Features

    • Sheer fishnet fabric
    • Crew neckline
    • Graphic and script that reads "Ibiza.
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000036

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Sun-Soaked Halter Open Back Paisley Crop Top

    Have a sun-soaked adventure in this paisley crop top this summer! Featuring a flattering halter V-neckline and spaghetti strap ties, along with an open back elasticized bar and a pointed crop hem to show off your figure. Complete the look in jean shorts and sunglasses.

    Fit & Features

    • Paisley print, knit fabric, minimal stretch
    • Halter V-neckline, spaghetti strap ties
    • Open back with elasticized bar
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2552

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Spice Lace-Up Ruffle Crop Top

    Set the tone in this spicy ruffled crop top with a lace-up back that turns heads! Pair with the matching shorts to complete the vibe.

    Fit & Features

    • Mesh-lined fabric
    • Cap sleeves
    • Crew neck
    • Ruffled crop hem
    • Bungee strap lace-up back
    • Runs true to size

     

    Shop The Matching Shorts: Summer Spice Low-Rise Ruffle Hot Shorts

    Style Number/Barcode: 06001-000033

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PINK, BLACK

    Available Size: S, M, L, XS

    Product Badge:
    • Sale
  • Stylish Striped Halter Crochet Midi Dress

    Stay stylish in this striped crochet midi dress for a sunny day by the beach or on vacation! It features a flattering halter neckline, adjustable spaghetti strap ties, and a bodycon fit that accentuates your curves along the midi-length hem. Complete the look with sunglasses and a tote bag!

    Fit & Features

    • Striped pattern, crochet fabric, short knit stretchy lining
    • Halter neckline with spaghetti strap ties
    • Bodycon fit
    • Midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2032

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blissful View Crochet Knit Midi Skirt

    Enjoy stylish bliss in this crochet midi skirt on your next getaway or weekend outing! The skirt offers a flattering high-rise waist, a bodycon fit, and a midi-length hem. Complete the look with the matching halter top.

    Shop Matching Top: Blissful View Halter Crochet Crop Top

    Fit & Features

    • Crochet knit fabric, geometric pattern, knit lining
    • High-rise waist, ribbed detail
    • Midi-length hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1140

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: LIGHT, BLUE, NATURAL

    Available Size: S, M, L, XS

    Product Badge:
    • Sale
  • Versatile Dream Strappy Faux Leather Block Heels

    A versatile pair of faux leather heels that can be styled with multiple outfits! They feature a sleek square toe, block heel, and a strappy design for a stylish touch. Complete the look with a trendy tote bag.

    Fit & Features

    • 3.5" Block heel
    • Square toe
    • Strappy design
    • Faux leather material
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4904

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Ready Tie-Front Bandeau Crochet Crop Top

    Heading on vacation? Don't forget to grab this vacay ready strapless crochet bandeau crop top with a sultry tie-front closure. Pair with the matching skirt and your fave shades!

    Fit & Features

    • Crochet fabric, stretchy knit lining
    • Strapless neckline
    • Tie-front closure
    • Ultra-cropped hem
    • Runs true to size 

     

    Shop The Matching Skirt: Vacay Ready High Rise Crochet Maxi Skirt

    Style Number/Barcode: 06003-2777

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Flirty Match Short Sleeve Tie-Front Top

    Flirt up your style in this crop top on vacation or weekend fun! The flowy short sleeves and cropped hem provide a flattering fit, while the tie-front design adds a touch of playful charm. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Flirty Match High-Rise Palazzo Pants

    Fit & Features

    • Woven fabric, no stretch
    • Tie-front design
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-1752

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ruffle and Ready Chiffon Halter Maxi Dress

    Love to make an entrance? Nail it with this chiffon maxi dress! With cascading ruffles, sultry cutouts, and a leggy slit, this chiffon maxi brings the drama every time.

    Fit & Features

    • Chiffon fabric, lined with stretchy knit
    • Sweetheart halter neckline with tie straps, padded bra cups
    • Cutout back and sides
    • Cascading ruffle trims
    • Flowy silhouette, front slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000198

    Category Name: Vacation Looks

    Price: $59.90

    Availability: In Stock

    Available Color: BROWN, BEIGE

    Available Size: S, M, L

  • Strolls In The Sand V-Neck Tropical Skater Mini Dress

    Getaway in this tropical skater mini dress to the beach or on vacay! Featuring adjustable spaghetti straps and a flattering V-neckline, this dress hugs your silhouette with an elasticized waist and side cutouts. Its skater silhouette and mini-length hem make it perfect for any daytime adventure. Complete the look in cute sandals.

    Fit & Features

    • Tropical print, woven fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • V-neckline
    • Elasticized waist with side cutouts
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5656

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Style Cowl Neck Slit Paisley Maxi Dress

    Bask in the aesthetic perfection of this paisley mesh maxi dress whether you're on vacation or having a sunset dinner with friends! This form-hugging dress features a cowl neckline and spaghetti straps, highlighting your figure in all the right ways. The high-side slit and sheer maxi-length hem add a touch of allure to this must-have dress! Complete the look with a necklace and earrings.

    Fit & Features

    • Paisley print, partially lined mesh fabric
    • Cowl neckline
    • Spaghetti straps
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5694

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Times Long Sleeve Striped Button Down Top

    Casually update your everyday look in this striped oversized top to pair with your favorite bottoms! It features a collar neckline, long sleeves with button cuffs, a button-down front, and a trendy oversized fit on poplin woven fabric for a polished look. Style this top with jean shorts, sandals, and sunglasses!

    Fit & Features

    • Striped print, poplin woven fabric, no stretch
    • Collar neckline
    • Button down front
    • Oversized fit
    • Runs true to size

    Style Number/Barcode: 06003-2627

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale