Vacation Looks

Loading...

STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • Keep It On Check Plaid Crop Jacket

    Keep your fall look in check in this plaid crop jacket perf for the cozy season! It features long sleeves, a collar neckline, snap-button front closures, flap pockets, and a pull tab hem with button closure. Complete the look in trendy boots.

    Fit & Features

    • Long sleeves, collar neckline
    • Snap-button front closures
    • Flap pockets
    • Pull tab hem with button closure
    • Cropped length
    • Plaid pattern, woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1421

    Category Name: Vacation Looks

    Price: $18.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Enticing Flirty Sleeveless Lace-Up Denim Romper

    Entice them all with your flirtiness in this denim romper perfect for festivals, concerts, or casual plans! Featuring a square neckline and adjustable thin tank straps, this romper hugs your curves and offers a flirty lace-up front. Perfect for a casual day out, and with a short-length hem, it's the ultimate summer must-have. Complete the look in trendy cowboy boots.

    Fit & Features

    • Dark wash cotton-blend denim fabric, moderate stretch
    • Square neckline
    • Adjustable tank straps
    • Back zipper with hook and eye closure
    • Lace-up
    • Form-hugging
    • Runs true to size

    Style Number/Barcode: 06603-0380

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love For Fall Plaid Cropped Shacket

    Showcase your love for this cozy season with this on-trend cropped shacket. It features a collared neckline, long sleeves, a multi-button down front, and a cropped, cinched back hem. The flannel woven fabric features an all-over plaid print, perfect for the fall time. Layer over a bodysuit with faux leather pants for an elevated look.

    Fit & Features

    • Collared neckline
    • Long sleeves, button details
    • Multi-button down front
    • Buttoned chest pockets
    • Cropped hem with a cinched back
    • Plaid print, flannel woven fabric
    • Runs true to size

    Style Number/Barcode: 06204-1450

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Chic Linen Tie-Front Corset Romper

    Show up looking casual-chic for your weekend plans in this adorable tie-front corset romper! Designed with a lightweight linen woven fabric, it features a sleeveless square neckline with adjustable spaghetti straps offering a customized fit leading to a back zipper closure. The corset bodice will create that cinched silhouette, followed by a tie-front belt for a cute touch. Style with espadrille wedges.

    Fit & Features

    • Linen woven fabric
    • Square neckline
    • Adjustable spaghetti straps, back zipper and hook-eye closure
    • Corset bodice, flexible boning
    • Tie-front belt, side pockets
    • Runs true to size

    Style Number/Barcode: 06303-0251

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vibe Of Summer Tie Front Eyelet Crop Top

    This gorgeous eyelet crop top will bring you the vibe of summer vacations and parties! The sweetheart neckline flatters your look while the tie front design and spaghetti straps add a playful touch to the cropped hem on breezy eyelet fabric. Complete the look with the matching maxi skirt.

    Shop Matching Bottoms: Vibe Of Summer High Rise Eyelet Maxi Skirt

    Fit & Features

    • Eyelet fabric, moderate stretch
    • Spaghetti straps
    • Sweetheart neckline
    • Tie front
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06001-5358

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Get Like Me Cutout Wide-Leg Jumpsuit

    Make a striking impression in this bold strapless jumpsuit on vacay or a summer night out! With O-ring inserts, a cutout bodice, and a flattering wide-leg fit, this jumpsuit will turn heads everywhere you go.

    Fit & Features

    • Smooth knit stretchy fabric, full knit lining
    • Strapless neckline
    • O-ring inserts, cutout bodice
    • Wide-leg fit
    • Runs true to size

    Style Number/Barcode: 06502-000036

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Festival Vibes Halter Crop Top

    Showcase trendy festival vibes all season with this alluring crop top! It features a sleeveless halter neckline with spaghetti straps in a cross-front design and a cropped, form-hugging fit. Style with the matching wide-leg pants and retro shades.

    Shop Matching Bottoms: Festival Vibes Wide-Leg Pants

    Fit & Features

    • Sleeveless halter neckline
    • Spaghetti straps, cross-front design, tie at the back of the neck
    • Cropped, form-hugging fit
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-4029

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Minimalistic Chic Faux Leather Belt

    Add the perfect touch of chic to your look with this faux leather belt featuring a sleek metal buckle accent, dual bands with perforated holes, and a pull-through design. Complete the look in a form-fitting jumpsuit and heels.

    Fit & Features

    • Sleek metal buckle accent
    • Dual faux leather bands
    • Perforated holes
    • Pull-through design

    Style Number/Barcode: 07301-0468

    Category Name: Vacation Looks

    Price: $3.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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
  • 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
  • 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
  • Kiss the Spotlight Halter Romper

    Flirty, flowy, and low-key iconic. This romper’s deep neckline and twirl-worthy shorts bring main feed energy to your night-out lineup.

    Fit & Features

    • Slinky knit stretchy fabric
    • Halter plunge neckline, tie straps
    • Open back
    • Flowy shorts hem
    • Runs true to size

    Style Number/Barcode: 06503-000079

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • 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: $9.97 $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: $9.97 $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