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.

  • Stay Forever Chic Faux Wool Hat

    You'll stay forever chic with this of-the-moment faux wool hat! It features a structured top with a wide flat brim and a sleek faux leather trim. Style with a mock neck bodysuit and your fave pair of denim.

    Fit & Features

    • Structured top
    • Wide flat brim
    • Thin faux leather trim, adjustable buckle detail
    • Faux wool material

    Style Number/Barcode: 07302-1394

    Category Name: Vacation Looks

    Price: $7.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirty Fun V-Neck Tie Striped Knit Crop Top

    Give your vacay style a dynamic upgrade in this flirty knit crop top perfect for a getaway or weekend fun! The top boasts a sultry V-neckline, dual tie-back design, and an ultra-cropped hem on pointelle knit fabric showcasing a trendy striped pattern. Complete the look with the matching skirt.

    Shop Matching Skirt: Flirty Fun High Rise Striped Knit Midi Skirt

    Fit & Features

    • Pointelle knit fabric, striped pattern
    • V-Neck
    • Dual tie-back design
    • Ultra-cropped length hem
    • Runs true to size

    Style Number/Barcode: 06005-1970

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cut It Out Babe Midi Dress

    Effortless, but make it extra. With a bold cutout bodice and sleek side slit, this midi dress hugs in all the right places for dates, brunch, or casual plans.

    Fit & Features

    • Stretchy rib knit fabric, contrast trim
    • Square neck, tank shoulder straps
    • Cutout bodice
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000045

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L

  • Cutie In A Lug Bootie

    Hey, there cutie rocking these lug sole booties! They feature a round toe, chunky block heel, and rib-knit upper design on faux leather material. Complete the look in a flannel shacket for cold-weather vibes. 

    Fit & Features

    • Almond toe
    • Lug sole
    • Chunky block heel
    • Rib-knit upper design
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1584

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming Vibe Tie-Back Flowy Floral Woven Maxi Dress

    Give off a charming vibe at summer parties in this simply stunning floral woven maxi dress! The breezy lightweight woven fabric is detailed with a gorgeous floral print pattern and includes a mini-length lining for coverage. The sleeveless bodice is shaped with a sweetheart neckline, a dainty tie-front bust design for a cute detail, and spaghetti straps leading to an open back with a cross-back strappy design and a customized tie closure. The fitted high waist flows out to a maxi-length hem with an effortlessly chic A-line silhouette. Style with hoop earrings and slip-on sandals.

    Fit & Features

    • Floral print
    • Lightweight woven fabric, mini-length woven lining, no stretch
    • Sweetheart neckline with tie-front bust, spaghetti straps
    • Open back, cross-back strappy design, tie closure
    • High waist seam
    • Flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3048

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Get Your Flirt On Floral Open Back Crop Top

    Have yourself a summer romance in this flirty floral crop top designed with a sultry open strappy back and a cropped hem that flaunts your figure!

    Fit & Features

    • Floral print, mesh-lined fabric
    • Scoop neckline
    • Sleek spaghetti straps
    • Open strappy back
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-000076

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L

    Product Badge:
    • Sale
  • In Search Of Luxe Gold Leaf Trim Hat

    Your search for luxe ends here with this faux wool hat! It features a stunning gold leaf trim on a thin faux leather band and a wide brim. Complete the look in a polished plaid blazer.

    Fit & Features

    • Gold leaf trim, thin faux leather band
    • Wide brim
    • Faux wool material

    Style Number/Barcode: 07302-1396

    Category Name: Vacation Looks

    Price: $5.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charmed By You Sleeveless Lace Crop Top

    Charm them all with your adorable flair in this sleeveless lace crop top! Made of soft knit floral lace fabric, it's both stylish and comfortable.  It features a square neckline, bungee spaghetti straps, and a ruched bust for a flattering fit. Complete your look with light-wash jeans and sneakers.

    Fit & Features

    • Floral lace knit fabric, sewn-in lining, moderate stretch
    • Bungee spaghetti straps
    • Square neckline
    • Cropped length 
    • Runs true to size

    Style Number/Barcode: 06001-5184

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Chic Wavy Striped Crochet Midi Skirt

    Wrap yourself in the retro chic wavy striped crochet midi skirt. With a high-rise waist and back slit, it's perfect for flaunting your style. Pair it with the matching top for a fab look!

    Fit & Features

    • Unlined crochet knit fabrication, short knit stretchy lining
    • High-rise waist
    • Wavy striped pattern
    • High center slit at back of hem
    • Midi length hem
    • Runs true to size

     

    Shop Matching Top: Retro Chic Wavy Striped Crochet Tube Top

    Style Number/Barcode: 06501-1107

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Wear Your Art Striped Midi Dress

    Wear this fine work of art and every eye will be on you! This marble striped midi dress features long sleeves, front and back v-necklines, a bodycon silhouette, and a tie-front waist. Complete the look in PVC mules for a casual lunch!

    Fit & Features

    • Long sleeves
    • Front and back v-necklines
    • Bodycon silhouette
    • Tie-front waist
    • Midi-length hem
    • Marble striped print, stretch-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4821

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet One Off-The-Shoulder Crop Top

    Show off your sweet side in this off-the-shoulder crop top perfect for summer fun! Features a sweetheart neckline and short sleeve cuffs for a flattering fit. The adjustable drawstring allows for a customizable look and the cropped hem adds a touch of trendiness. Complete the look in denim shorts and sandals for a day out!

    Fit & Features

    • Stretchy rib knit fabric
    • Off-the-shoulder, sweetheart neckline
    • Adjustable drawstring
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06002-1865

    Category Name: Vacation Looks

    Price: $22.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Mode Button-Down Cotton Top

    Activate summer mode with this lightweight cotton button-down top featuring a collared neckline, long sleeves, and a relaxed, long-length fit. Style with the matching bra top and high-rise shorts for an effortlessly chic look.

    Shop Matching Set: Summer Mode Cotton Bra Top, Summer Mode High-Rise Cotton Shorts

    Fit & Features

    • Textured cotton fabric, no stretch
    • Collared neckline
    • Complete button-down front
    • Long sleeves, single button detail
    • Long-length hem, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06003-000081

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: CHARTREUSE

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Next Level Faux Suede Mini Skirt

    Take your look to the next level with a mini skirt that slays! The skirt features a high-rise waist, a lattice tie-up front, and a mini-length hem. The skirt is composed of a lined faux suede fabric that offers a form-hugging fit with slight stretch. Complete look with a crop top and wedges. 

    Fit & Features

    • High-rise waist
    • Back zipper closure
    • Lattice-tie front 
    • Mini-length hem
    • Lined faux suede fabric
    • Form-hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 06401-0457

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweetly Femme Floral Corset Lace-Up Mini Dress

    Sure to be a staple in your rotation, this super sweet floral mini dress is designed with a corset bodice and lace-up back that accentuates your femme figure along the A-line silhouette. 

    Fit & Features

    • Floral print, chiffon-lined fabric
    • Sweetheart neckline, bust tie, underwire bust
    • Wide shoulder straps, side zipper and hook-eye clsoure
    • Corset bodice, lace-up back
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4054

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortlessly Pretty Chiffon Midi Dress

    Showcase your effortless beauty in this airy, lightweight chiffon midi dress. It features a sweetheart neckline with a ruched bodice, long sheer peasant sleeves, a stretchy smocked back design, a fitted high waist seam, a midi-length hem with a high front slit, and a flowy, A-line silhouette. Style with clear mules for a weekend brunch date.

    Fit & Features

    • Sweetheart neckline, ruched bodice
    • Long sheer peasant sleeves, elastic cinched hems
    • Stretchy smocked back design
    • Fitted high waist seam
    • Midi-length hem, high front slit, A-line silhouette
    • Sheer chiffon fabric, partial knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4954

    Category Name: Vacation Looks

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 90s Classic Patchwork Denim Bucket Hat

    Experience the nostalgia of the 90s with this trendy patchwork denim bucket hat! It features a classic patchwork design on denim material and has adjustable inner strings to get the perfect fit. Complete the look in a denim mini dress!

    Fit & Features

    • Patchwork design, denim material
    • Adjustable inner strings
    • Bucket hat style

    Style Number/Barcode: 07302-1614

    Category Name: Vacation Looks

    Price: $4.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wanting More Strapless Lace Knit Maxi Dress

    Leave everyone wanting more when you're in this lace knit maxi dress! Perfect for any summer plans, this dress flaunts a sleek strapless neckline and form-hugging fit that flares out into a long hem.

    Fit & Features

    • Lace knit fabric, lined
    • Strapless neckline
    • Form-hugging fit
    • Flared maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000057

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Seal The Deal Trouser Joggers

    These casual and chic trouser joggers will have you business ready to take on the day! They feature a high-rise waist, pintuck pleated detailing, dual front pockets, a relaxed fit, and a trendy jogger hem. The lightweight woven fabric has no stretch. Style these pants with a bodysuit and a structured blazer.

    Fit & Features

    • High-rise waist, belt loops
    • Hidden front zipper, hook and bar, and button closure
    • Pintuck pleated detailing
    • Dual front pockets
    • Relaxed fit, elasticized jogger hem
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06402-1280

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wanderlust Calling Strapless Abstract Flowy Tunic Top

    Breeze into the sunny season in this strapless tunic top with a pretty abstract print on a flowy long silhouette and a flirty center slit design. Style as a cover-up or by itself on vacation, at festivals, or a beach day!

    Fit & Features

    • Abstract print, sheer chiffon fabric
    • Strapless neckline with metal insert, bust lining
    • Center slit design
    • Flowy long silhouette
    • Runs true to size

    Style Number/Barcode: 06003-2751

    Category Name: Vacation Looks

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Gorgeous Lace-Up Striped Maxi Dress

    Look gorgeous everywhere you go in this striped maxi dress! Featuring a flattering halter crew neck and a chic lace-up back, this bodycon fit dress hugs your curves for a stunning silhouette. 

    Fit & Features

    • Striped pattern, stretchy cotton knit fabric
    • Halter crew neck
    • Lace-up open back
    • Bodycon fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000009

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M

    Product Badge:
    • Sale
  • Romance Forever V-Neck Bow Floral Lace Top

    Romance your look with this floral lace top boasting a delicate satin bow and sheer bodice that flaunts your figure.

    Fit & Features

    • Floral lace fabric, bust knit lining
    • V-neckline, satin bow
    • Adjustable spaghetti straps
    • Sheer bodice
    • Fitted mid-length hem
    • Runs true to size

    Style Number/Barcode: 06001-000009

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Alluring Marble Mesh Bodycon Dress

    This alluring marble mesh bodycon dress will draw all the attention your way! It features a square neckline, sheer long fitted sleeves, a short, curve-hugging silhouette, and an all-over marble swirl pattern. The partially lined mesh fabric offers plenty of stretch. Style with platform heels.

    Fit & Features

    • Square neckline
    • Sheer long fitted sleeves
    • Mini-length hem
    • Fitted bodycon silhouette
    • Marble swirl pattern
    • Sheer mesh fabric, partial knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4863

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Flirt Floral Mesh Mini Skirt

    Bold and flirty will be your vibe in this mini skirt featuring a large floral print to turn heads. The mid-rise waist paired with the short form-hugging fit create a sultry silhouette.

    Shop Matching Top: Bold Flirt Floral Mesh Tube Top

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Large floral print
    • Mid-rise waist
    • Mini-length hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-000002

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: L

    Product Badge:
    • Part of a Set
  • Faux Leather Paper Bag Tie Waist Shorts

    Create a sleek and edgy look in these faux leather paper bag shorts. Step out in style in these high-waist shorts with side pockets and a matching self-tie belt. The faux leather material instantly makes dressy shorts the perfect bottoms to pair with your going-out looks for a girls' night out or clubbing. Pair these faux leather shorts with a mesh bodysuit or sparkly corset top for a fierce and sexy look.

    Fit & Features

    • High-rise paper bag waist
    • Tie front belt
    • Back zipper, hook and eye closure
    • Side pockets
    • Form-fitting style
    • Faux leather fabric with moderate stretch
    • Runs true to size

    Style Number/Barcode: 06403-0146

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance