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.

  • Sweet Spice Corset Lace-Up Floral Midi Dress

    Sweet and spice combine on this floral midi dress designed with a stylish lace-up back, corset bodice, and a flirty front slit for movement. Complete the look with mules.

    Fit & Features

    • Ditsy floral print, smooth woven fabric, woven lining
    • Sleeveless sweetheart neckline with tie
    • Shoulder straps, side zipper and hook-eye closure
    • Lace-up back design
    • Underwire bust, corset bodice
    • Front slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3819

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Delicate Essence Puff Sleeve Corset Lace Mini Dress

    The delicate essence of this lace mini dress will have you looking so cute at a bridal shower, as the birthday girl or graduate! Featuring sheer puff sleeves, an underwire bust for support, and flexible boning for a flattering bodycon fit. The front ruched seam adds a touch of sophistication to this playful mini-length dress. Complete the look in cute sandals and a purse!

    Fit & Features

    • Lace fabric lined with stretchy knit
    • Back zipper and hook-eye closure
    • Sweetheart neckline, underwire bust
    • Flexible boning
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3226

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt And Twirl Puff Sleeve Tie-Back Skater Dress

    Flirt and twirl in this cute skater dress at parties and day dates! The puff short sleeves and square neckline add a touch of charm, while the tie-back design and skater silhouette create a flattering fit. Complete the look with hoop earrings.

    Fit & Features

    • Crepe woven fabric, stretchy knit lining
    • Square neckline
    • Tie-back detail
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3243

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love's In The Air Floral Chiffon A-Line Dress

    Slip into romance! This dainty floral chiffon short dress features a sweetheart neckline and bust tie to accentuate your figure while the wide shoulder straps and underwire bust provide support. The corset-trim bodice and back lace-up design add a touch of romance along the flattering A-line silhouette and short-length hem. Complete the look with a ring set and sandals for a date or brunch!

    Fit & Features

    • Sleeveless sweetheart neckline
    • Wide shoulder straps
    • Underwire bust, tie front, side zipper and hook-eye closure
    • Corset-trim bodice, lace-up back design
    • A-line silhouette, short-length hem
    • Dainty floral print, chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-3007

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fresh Vibe High-Rise Destructed Straight-Leg Jeans by Windsor Denim

    These trendy destructed straight-leg jeans by Windsor Denim will give you that fresh vibe you crave for the summer season. Made with a stretchy cotton-blend denim fabric, they feature a high-rise waist and a straight-leg fit with destructed detailing for an effortlessly cool look. Include a five-pocket and belt loop design with a front button and hidden zipper closure. Style these jeans with a graphic tee and ankle booties.

    Fit & Features

    • Cotton-blend denim fabric with moderate stretch
    • High-rise waist
    • Straight-leg fit
    • Destructed detailing
    • Five-pocket and belt loop design
    • Front button, zipper closure
    • Runs true to size

    Style Number/Barcode: 06602-0492

    Category Name: Vacation Looks

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Moves Plunging Halter Bodycon Mini Dress

    Make sultry moves with all eyes on you in this sexy bodycon mini dress your next night out! The slinky knit fabric offers plenty of stretch for that perfect comfortable fit. The mini-length dress is shaped with a sleeveless plunging V-neckline with a halter strap design, an open back for even more allure, lower back ruching to accentuate your curves, and a bodycon silhouette to flaunt your gorgeous figure. Style with a rhinestone lariat necklace and stiletto heels.

    Fit & Features

    • Stretchy knit fabric, knit lining
    • Plunging V-neckline
    • Halter straps
    • Open back
    • Back ruching
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5659

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Easy And Breezy Lace-Up Midi Dress With Pockets

    So effortlessly breezy for any plans, this A-line midi dress will turn heads with a lace-up bust and back detail, while the hidden side pockets are perfect for stashing your phone or lip gloss in.

    Fit & Features

    • Poplin woven fabric, woven lining
    • Sweetheart neckline, lace-up front, stretchy smocked bust
    • Spaghetti straps
    • Lace-up back, lower zipper and hook-eye closure
    • Drop waist seam, hidden side pockets
    • A-line silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6023

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Fun Rhinestone Pineapple Stud Earrings

    Add a touch of tropical fun to your look with these juicy, cute pineapple stud earrings embellished with sparkling rhinestones.

    Fit & Features

    • Pineapples
    • Rhinestone embellished
    • Post-back closure

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-000057

    Category Name: Vacation Looks

    Price: $2.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Crush Marble Print Maxi Dress

    They'll totally be crushing on you in this alluring abstract marble print maxi dress! It features a strapless straight-across neckline, ruching down one side seam with an adjustable drawstring, a sultry high-cut side slit, and an asymmetric maxi-length hem. The fitted bodice leads to a flowy silhouette. The marble-printed sheer mesh fabric includes a mini-length knit lining. Style with gemstone earrings.

    Fit & Features

    • Strapless straight-across elastic-banded neckline
    • Ruching down one side seam, adjustable drawstring
    • High-cut side slit, asymmetric maxi-length hem, lettuce-edge trim
    • Fitted bodice, flowy silhouette
    • Abstract marble print
    • Sheer mesh fabric, mini-length knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5276

    Category Name: Vacation Looks

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Three Way Tie Layered Bead Necklace

    This layered necklace will win your heart! This stunning necklace features one beaded layer, one dainty beaded chain layer accented with mini clear stones, and one paperclip chain layer, creating a unique and versatile piece. Complete the look in a cute midi dress for a party!

    Fit & Features

    • Three-row layered design
    • One beaded layer
    • One beaded chain layer with mini clear stones
    • One paperclip chain layer
    • Lobster clasp closure

    Style Number/Barcode: 07002-1879

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Raise The Bar Wide-Leg Jumpsuit

    Raise the bar and strut in this sleeveless jumpsuit featuring a statement design with a plunge halter neckline and an alluring open back. Complete the look with earrings.

    Fit & Features

    • Smooth knit fabric, plenty of stretch
    • Plunging sleeveless halter neckline
    • Halter neck ties
    • Open back
    • Wide-leg silhouette
    • Jumpsuit in size small is 58" shoulder to hem with a 13" front rise and a 30" inseam
    • Runs true to size

    Style Number/Barcode: 06502-2551

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Divine Cutie Tie-Back Ruffled Skater Dress

    You'll look positively cute and divine in this short skater dress at brunch or graduations! Designed with a flattering square neckline, adjustable spaghetti straps for the perfect fit, and a tie-back design, this dress is perfect for every girlie. The skater silhouette and ruffled layer add a playful touch, while the short-length hem offers comfort and versatility. Complete the look in strappy mules.

    Fit & Features

    • Airy woven fabric, sewn-in knit lining
    • Adjustable spaghetti straps
    • Ruffled
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5733

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Enchanting Look V-Neck Button Down Skater Dress

    Your day just got sweeter in this sleeveless skater dress perfect for spring and summer occasions! This V-neck skater dress boasts adjustable spaghetti straps and button closures that allow for the perfect fit while the skater silhouette and short-length hem elevate your style. Complete the look with sandals and sunnies!

    Fit & Features

    • Woven fabric with lining, no stretch
    • Adjustable spaghetti straps
    • V-Neckline
    • Button down front
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5555

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sparkling Delight Rhinestone Strappy Sandals

    These sparkling sandals bring dazzling delight to any look! They're designed in a rhinestone embellished strappy design and a flat sole for comfort.

    Fit & Features

    • Square toe
    • Rhinestone-embellished strappy design
    • Flat sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-000025

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Addition Dainty Stone Threader Earrings

    These dainty stone threader earrings will be a chic addition to your jewelry lineup! They feature a long delicate chain threader design accented with small teardrop clear stones at the front and sleek bar detailing at the back. Style with a layered necklace for a trendy luxe vibe.

    Fit & Features

    • Long dainty chain threader design
    • Front teardrop clear stone accents
    • Back bar accents
    • Rubber stopper

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-2039

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy Sparkle Celestial Charm Lariat Necklace

    This celestial charm lariat necklace will showcase the dreamiest sparkle! It features a dainty chain, an O-ring and toggle closure, a long cascading lariat design, shimmering rhinestones, and sleek moon and star charms for a trendy pop. Pair with stud earrings.

    Fit & Features

    • Dainty chain
    • O-ring and toggle closure
    • Rhinestones
    • Moon and star charms
    • Long lariat design

    Style Number/Barcode: 07002-1846

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Poolside Paradise Floral Scrunch Bikini Bottoms

    So pretty and made for tanning, these floral bikini bottoms offer a flattering V-shaped low-rise waist and a scrunched thong back that flaunts your curves! Pair with the matching bikini top.

    Shop Matching Top: Poolside Paradise Floral Triangle Bikini Top

    Fit & Features

    • Floral print, stretchy knit fabric
    • V-shaped low-rise waist
    • Scrunched thong back coverage
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000010

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stand Out Texture Oval Hoop Earrings

    Stand out in these hoop earrings featuring a textured oval design and post-back closures. Perfect for styling your everyday outfits.

    Fit & Features

    • Textured oval design
    • Post-back closure

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-2063

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Babe Gingham Print Bandeau Bikini Top

    Channel that flirty babe style in this adorable gingham printed bandeau bikini top with a ruffled trim. Pair with the matching bikini bottoms for a sweet and sassy look.

    Shop Matching Bottoms: Flirty Babe Gingham Print Side Tie Bikini Bottoms

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Gingham print
    • Strapless neckline
    • Center bust cutout, tie-front detail
    • Ruffled trim
    • Thin strappy back design, hook and bar closure
    • Runs true to size

    Style Number/Barcode: 07104-0718

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Head Turner Floral Bodycon Mini Dress

    With a sultry strut and this floral mini dress, you'll be a major head turner on vacation or at parties! 

    Fit & Features

    • Floral print, knit-lined stretchy fabric
    • Strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000103

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty Chic Floral Chain Necklace

    This cute necklace features a dainty flat floral chain design perfect for adding to your layered necklace stack. Complete your pretty chic look with hoop earrings.

    Fit & Features

    • Dainty flat floral chain
    • Back adjustable chain with lobster clasp closure

    Style Number/Barcode: 07002-1862

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Romantic Allure Flutter Sleeve A-Line Lace Mini Dress

    Indulge in the romantic allure of this lace mini dress with pretty flutter short sleeves and a flattering A-line silhouette. Perfect for shower celebrations, graduations, or brunch!

    Fit & Feature

    • Lace lined fabric
    • Flutter short sleeves
    • V-neckline
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4015

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charmed Sweetness Lace-Up Floral Skater Dress

    Charm everyone with your sweetness in this floral skater dress with a flirty lace-up back and a ruffled short hem perfect for any weekend plans.

    Fit & Features

    • Floral print, woven fabric, bust lining
    • V-neckline, wide shoulder straps, padded bra cups
    • Lace-up back
    • Ruffled skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5622

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • New Moon Star Charm Layered Necklace

    Get in touch with your celestial style in this layered necklace featuring a moon and star charm and mini clear stones that put your outfit out of this universe! Complete the look in heels.

    Fit & Features

    • Two-row layered design
    • Moon and star charm
    • Mini clear stones
    • Lobster clasp closure

    Style Number/Barcode: 07002-1870

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale