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.

  • Glam Life Off The Shoulder Gauze Romper

    Live that glam life with a romper that showcases your style! The romper features an elastic off-the-shoulder neckline, long bell sleeves, a tie waist belt, and wide-leg shorts. Complete look with wedges

    Fit & Features

    • Elastic off the shoulder neckline 
    • Long bell sleeves
    • Tie-waist belt 
    • Wide leg shorts
    • Gauze knit fabric 
    • Relaxed fit, minimal stretch 
    • Runs true to size 

    Style Number/Barcode: 06303-0126

    Category Name: Vacation Looks

    Price: $16.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Golden Hour Wide Leg Pants Energy

    She’s luxe, bold, and lowkey lethal. These tropical wide-leg pants brings the heat wherever you wear her—beach club or rooftop takeover. Pair with the matching top.

    Shop Matching Top: Golden Hour Tube Top Energy

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Mid-rise waist
    • Wide-leg fit
    • Runs true to size

    Style Number/Barcode: 06502-000032

    Category Name: Vacation Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Faux Leather Criss-Cross Braided Sandals

    Bring the glamour with sandals that showcase trendy details! The sandals feature a slip-on design, an open square toe, wide braided criss-cross straps. Sandals are composed of a faux leather material. Complete the look with a basic tee and cutoff shorts

    Fit & Features

    • Slip-on design 
    • Open square toe
    • Wide braided criss-cross straps
    • Faux leather material

     

    Style Number/Barcode: 07404-0712

    Category Name: Vacation Looks

    Price: $13.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Babe Faux Leather Sandals

    You'll look like a total trendy babe when you style up your look with these sandals! They feature a round open toe with double-banded straps and a slide-on design. The sandals have a flat sole and are composed of a sleek faux leather material. Pair these shoes with mom jeans and a graphic tee.

    Fit & Features

    • Round open toe
    • Double-banded straps
    • Slide-on design
    • Flat sole
    • PU material
    • Runs true to size

    Style Number/Barcode: 07404-0721

    Category Name: Vacation Looks

    Price: $12.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Babe Faux Leather Cork Block Heels

    Keep it trendy with heels that slay your look! The heels feature an open back, an adjustable ankle strap, a T-strap accent, an open almond toe with a caged design, a cork wedge, and a block heel. Complete look with a ribbed midi dress

    Fit & Features

    • Open back 
    • Adjustable ankle strap 
    • T-strap accent 
    • Open almond toe with caged design 
    • Cork platform and block heel 
    • Faux leather 

    Style Number/Barcode: 07401-2983

    Category Name: Vacation Looks

    Price: $7.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Step Up Your Style Anklet Set

    Step up your style with this trendy set of anklets! The pack features four anklets with dainty and thick metal chain designs, one featuring a cute butterfly charm. Style all four anklets together with your fave pair of sandals.

    Fit & Features

    • Set of four anklets
    • Dainty to thick metal chain designs
    • Butterfly charm

    Style Number/Barcode: 07003-0206

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dainty Detailed Lace Crop Top

    You'll fall in love with the dainty details of this pretty lace crop top! It features an off-the-shoulder neckline with a ruffled trim, short fitted sleeves, a double tie-front design, an open front, and a cropped, form-hugging fit. The sheer lace fabric has a front lining. Style this top with cutoff denim shorts and sandals.

    Fit & Features

    • Off-the-shoulder neckline, ruffled trim
    • Short fitted sleeves
    • Double tie-front design
    • Open front
    • Cropped, form-hugging fit
    • Sheer lace fabric, front lining
    • Runs true to size

    Style Number/Barcode: 06001-3306

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lovely In Linen Sleeveless Skater Dress

    Get a lovely look this season in this flowy linen skater dress! It features a sleeveless bodice, tank shoulder straps, a V-neck and back, a high waist with trendy bar cutouts on each side, and a flirty skater silhouette. Style this dress with sandals for a breezy vacay outfit.

    Fit & Features

    • Tank shoulder straps
    • V-neck and back
    • High waist, bar cutouts on each side
    • Flowy skater silhouette
    • Linen and gauze fabric
    • Runs true to size

    Style Number/Barcode: 05102-0241

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Status Quilted Faux Leather Sandals

    Elevate your chic status with these must-have slide-on sandals. They feature an open round toe, a thick criss-cross strap design, a flat sole, and a quilted faux leather material. Style these sandals with a casual dress and chic shades.

    Fit & Features

    • Open round toe
    • Thick criss-cross strap design
    • Flat sole
    • Quilted faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-0801

    Category Name: Vacation Looks

    Price: $12.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shell We Dance Crochet Hanky Top

    Your boho era just called and said to wear this. This crochet hanky top brings flirty vibes with a strapless fit and fringe shell trim, perfect for beach days, brunch dates, or dancing barefoot in the sand.

    Fit & Features

    • Crochet fabric, stretchy knit lining
    • Strapless tube neckline
    • Hanky hem with shell trim
    • Runs true to size

    Style Number/Barcode: 06005-000078

    Category Name: Vacation Looks

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Glam Platform Cork Heels

    Get a casual glam look this summer season in these adorable cork heels! They feature an open round toe, a thick criss-cross strap design, an adjustable ankle strap, and a cork platform and block heel. Style these trendy heels with a floral dress and chic shades.

    Fit & Features

    • Open round toe
    • Thick criss-cross strap design
    • Adjustable ankle strap
    • Open back
    • Cork platform and block heel
    • Runs true to size

    Style Number/Barcode: 07401-2984

    Category Name: Vacation Looks

    Price: $7.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless And Chic Eyelet Mini Dress

    Effortless and chic, this eyelet mini dress is the perfect addition to your summer wardrobe. It features a sleeveless scoop neckline, tank shoulder straps, and a mini-length, curve-hugging silhouette. Style this dress with strappy sandals.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Short, form-hugging fit
    • Sheer eyelet fabric, full lining
    • Runs true to size

    Style Number/Barcode: 05102-1275

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bohemian Beauty Flare Pants

    You'll be a total bohemian beauty in these on-trend flare pants! They feature a high-rise waist, a form-hugging fit, a flared-out hem, and an all-over bohemian-inspired print. Style these knit pants with a basic crop top and sandals.

    Fit & Features

    • High-rise waist
    • Form-hugging fit
    • Flared-out hem
    • Bohemian-inspired print
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-0596

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Plunging Into Basics Surplice Jumpsuit

    Take the plunge into a basic jumpsuit that keeps it part casual, part stylish. The jumpsuit features a sleeveless wrap V-neckline with spaghetti straps, an elastic waistband, hidden side pockets, and a straight leg fit with an elastic hem. The jumpsuit is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with mules and statement earrings. 

    Fit & Features

    • Sleeveless wrap V-neckline
    • Spaghetti straps
    • Elastic waistband
    • Hidden side pockets
    • Straight leg fit with elastic hem 
    • Lightweight woven fabric, relaxed fit, minimal stretch 
    • Runs true to size 

    Style Number/Barcode: 06302-0202

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Elevated Basics High Waist Paperbag Shorts

    Elevate your basic fits with paper bag shorts that are so on-trend! The shorts feature a high-rise paper bag waist, a hidden zipper front, a tie waist belt with belt loops, slant pockets, and cuffed hem. Complete look with a blouse and denim jacket for a cute casual outfit.

    Fit & Features

    • High-rise paper bag waist
    • Hidden front zipper and hook and bar closure
    • Tie-waist belt with belt loops
    • Slant pockets, cuffed hem
    • Woven fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06403-0158

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Glow N' Shimmer Low Rise Bikini Bottoms

    Chase that glow in these shimmery bikini bottoms! They feature a low rise waist and a cheeky fit. They are composed of a glitter lurex fabric that offers a form hugging fit. Complete your vacation outfit with the matching bikini top. 

    Shop Matching Bikini Top: Glow N' Shimmer Bikini Top

    Fit & Features

    • Low-rise waist
    • Cheeky fit
    • Glitter lurex
    • Matching bikini top sold separately 

     

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07105-0517

    Category Name: Vacation Looks

    Price: $5.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Era V-Neck Ruffled Romper

    Enter your sweet girl era in this eyelet romper perfect for brunch, graduations, or shower celebrations! The V-neck and form-hugging bodice create a flattering silhouette, while the ruffled hem adds a playful touch.

    Fit & Features

    • Eyelet knit fabric
    • V-neckline
    • Spaghetti straps
    • Form-hugging bodice
    • Ruffled skirt overlay, shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000032

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glow N' Shimmer Bikini Top

    Chase that glow in this shimmery bikini top! It features a plunging sweetheart neckline, demi-cups, underwire, adjustable spaghetti straps, and a slide-hook fasten closure. Complete your vacation outfit with the matching bikini bottoms.

    Shop Matching Bikini Bottoms: Glow N' Shimmer Low Rise Bikini Bottoms

    Fit & Features

    • Sleeveless sweetheart neckline
    • Demi-cups
    • Underwire
    • Adjustable spaghetti straps
    • Slide-hook fasten closure
    • Matching bikini bottoms sold separately

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0368

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming Stunner Floral Skater Dress

    Bring the charm in this stunning floral skater dress. It features ruffle detail shoulder straps, a wrap-front V-neckline with a ruffle overlay, an open back with a tie closure, a waist tie accent, and a flirty skater skirt with a tiered ruffle design. Style this chiffon dress with hoop earrings and sandals.

    Fit & Features

    • Ruffle detail shoulder straps
    • Wrap-front V-neckline, ruffle overlay
    • Open back, tie closure, back zipper and hook and eye closure
    • High waist, tie-front
    • Skater skirt, tiered ruffle design
    • Floral chiffon fabric, knit lining
    • Runs true to size

    Style Number/Barcode: 05101-1004

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Vibes Tie Dye Mini Dress

    Channel retro vibes with a mini dress that keeps it super cute! The dress features a sleeveless crew neckline, a tie-dye print, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a relaxed fit with a moderate stretch. Complete look with clear mules to let this print take center stage! 

    Fit & Features

    • Sleeveless
    • Crew neckline
    • Tie-dye print
    • Mini length silhouette
    • Brushed knit fabric
    • Relaxed fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1096

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stand Out In Stripes Tie Front Crop Top

    Stand out in stylish stripes with a top that elevates your casual outfits. The top features a striped pattern, plunging V-neckline with tie-front, quarter length sleeves with elastic hem, and a cropped hem. Complete look with high waist jeans

    Fit & Features

    • Plunging V-neckline 
    • 3/4 sleeves
    • Striped pattern 
    • Tie Front
    • Cropped hem 
    • Lightweight woven fabric 
    • Relaxed fit, minimal stretch, runs true to size  

    Style Number/Barcode: 06204-0888

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Seeing Stars Necklace Multi Pack

    Channel a starry-eyed look with this cute necklace pack! The pack includes three necklaces with galactic-inspired designs. One necklace features a snake chain, one features a crescent moon charm, and one necklace features a starburst-designed charm with a rhinestone center accent. Complete look with a crop top and shorts.

    Fit & Features

    • Pack includes three necklaces
    • Snake chain 
    • Crescent moon
    • Starburst design with rhinestone center
    • Lobster clasp closure 

    Style Number/Barcode: 07002-0725

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sippin' On Henny Cap

    Let this cap say it all! The cap features a traditional baseball cap design and a script that reads "Henny" with olive branch accents. Complete look with a crop top and cutoff shorts for a laid-back look.

    Fit & Features

    • Baseball cap design 
    • "Henny" script 
    • Olive branch accent
    • Adjustable strap

    Style Number/Barcode: 07302-0314

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Allure Ruched Mini Skirt

    Let those tropic vibes allure you in with this cute mini skirt! The skirt features a high-rise waist, a tropical palm leaf print, ruched side seams, and a mini-length silhouette. Complete look with the matching crop top and wedges that will have you vacay ready! 

    Shop Matching Crop Top: Tropical Allure Mesh Crop Top

    Fit & Features

    • High rise waist 
    • Tropical palm leaf print
    • Mini length silhouette
    • Lined mesh fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06501-0400

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free