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.

  • The Bottom Line High-Rise Parachute Cargo Pants

    The bottom line? You need these cargo parachute pants to add to your weekly rotation! They feature a flattering high-rise waist with a back elastic band, a loose-fit leg silhouette, flap pockets, and an adjustable draw cord along the hem to get the perfect cinched look. Style with a basic crop top and sneakers for hanging out with friends!

    Fit & Features

    • High-rise waist, back elastic band
    • Loose-leg silhouette
    • Adjustable drawcord at the hem
    • Four open front pockets, faux back pockets
    • Hidden front hook and zipper closure, belt loop accents
    • Lightweight nylon woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0743

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirt And Flutter Three-Pack Anklet Set

    Flirt and flutter! This charming three-pack anklet set features two dainty anklets and one anklet with rhinestone trim and a butterfly charm. Each has a lobster clasp closure. Complete the look in a whimsical skater dress.

    Fit & Features

    • Three-pack anklet set
    • Two dainty anklets
    • One anklet with rhinestone trim and butterfly charm
    • Each has a lobster clasp closure

    Style Number/Barcode: 07003-0555

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Of-The-Moment Chic Swirl Print Midi Dress

    This of-the-moment chic swirl print midi dress is perf for happy hour! It features a sleeveless V-neckline, bungee spaghetti straps, a hip-hugging fit that flows out to a midi-length A-line silhouette, and a sultry front slit. The smooth jersey knit fabric showcases an alluring all-over swirl print pattern. Style with a faux leather blazer and strappy stilettos.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Hip-hugging fit, midi-length A-line silhouette
    • Thigh-high front slit
    • Swirl print pattern
    • Jersey knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4817

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Radiate Romantic Vibes Strapless Floral Chiffon Maxi Dress

    Radiate romantic vibes in this strapless floral chiffon maxi dress at garden parties or showers! The long ruffled silhouette adds flow and movement while the floral chiffon fabric adds a touch of femininity. Perfect for any occasion, this dress will make you stand out with its playful and flirty style! Complete the look with teardrop earrings.

    Fit & Features

    • Floral printed chiffon fabric with stretchy knit lining
    • Strapless neckline
    • Back zipper and hook-eye closure
    • Ruffled flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3044

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Just Like A Dream Strappy Back Ruffled Maxi Dress

    Make a jaw-dropping entrance in this gorgeous ruffled maxi dress at shower celebrations or on vacation! The flattering V-neckline draws the eye, while the intricate strappy back adorned with beaded insets creates an unforgettable exit view.

    Fit & Features

    • Airy woven gauze fabric, woven lining
    • V-neckline
    • Dual spaghetti straps
    • Strappy back with beaded insets
    • Cascading ruffles, flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000653

    Category Name: Vacation Looks

    Price: $59.90

    Availability: In Stock

    Available Color: RED, BROWN

    Available Size: XS, S, M, L, XL

  • Ready, Set, Slay Wrap Crop Denim Jacket

    Ready to slay? Cause this denim jacket is your perfect pairing for trending all season! It features long sleeves, a lapel collar plunge neckline, and a wrap-tie cropped hem that lets you customize the style. Complete the look with matching bottoms.

    Shop Matching Bottoms: Ready, Set, Slay V-Waist Denim Mini Skirt

    Fit & Features

    • Long sleeves
    • Lapel collar plunge neckline
    • Wrap-tie cropped hem
    • Medium-wash denim fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06203-0505

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • City Slicker High-Rise Faux Wrap Denim Skort

    A perfect denim mini skort for a cute look in the city! Designed in a flattering high-rise wrap silhouette that gives it a contemporary touch.

    Fit & Features

    • Denim fabric, non-stretch
    • High-rise waist dual button closures
    • Faux wrap design
    • Shorts bottom
    • Mini-length
    • Runs true to size

    Style Number/Barcode: 06603-0441

    Category Name: Vacation Looks

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Catch Flights Crochet Sweater Topper

    She’s giving jet-setter vibes with just a touch of drama. Layer this crochet sweater topper over your fave tanks or dresses when your outfit needs a little extra flirt.

    Fit & Features

    • Sheer crochet knit fabric
    • Long sleeves with flare cuffs
    • Boat neckline
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-000105

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless And Breezy Short T-Shirt Dress

    Style up this effortless and breezy short T-shirt dress for your casual weekend plans! It features a crew neckline, short sleeves, dual side pockets, a loose T-shirt fit, a short-length hem, and an A-line silhouette. The cotton-blend fabric has a moderate stretch. Pair with hoop earrings and strappy sandals.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Dual side pockets
    • Loose T-shirt fit
    • Short-length hem, A-line silhouette
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5044

    Category Name: Vacation Looks

    Price: $8.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Walk The Line Crepe Geo Mini Dress

    Walk the line into this artsy geometric print crepe dress to give your closet must needed prints! It features a sleeveless V-neckline, sleek bungee spaghetti straps, a bodycon silhouette, and a flirty slit along the mini-length hem. Complete the look in heeled sandals for a casual brunch downtown!

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Bodycon silhouette
    • Front slit, mini-length hem
    • Geometric print
    • Stretchy crepe fabric
    • Runs true to size

    Style Number/Barcode: 05102-4849

    Category Name: Vacation Looks

    Price: $6.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Faux Leather Mini Bag

    Carry your essentials in this chic faux leather mini bag to adorn your OOTD! Features a top handle with a scrunched design, a snap-button closure, and a spacious lined interior. Complete the look with a sleek necklace and earrings.

    Fit & Features

    • Faux leather material
    • Top handle 
    • Mini scrunched design
    • Snap-button closure
    • Spacious lined interior

    Style Number/Barcode: 07201-0136

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Western Charm Cactus Drop Earrings

    Show off a cute western charm with these cactus drop earrings! They feature a textured circular post with a hanging cactus charm with an engraved boho-inspired design. Include a post-back closure. Style with a flowy summer dress and cowboy boots!

    Fit & Features

    • Textured circular post
    • Hanging cactus charm, engraved boho-inspired design
    • Post-back closure


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

    Style Number/Barcode: 07001-1645

    Category Name: Vacation Looks

    Price: $3.96 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Remy High-Rise Acid-Wash Denim Shorts by Windsor Denim

    Create a bold festival-inspired look with the Remy acid-wash denim shorts by Windsor Denim! They feature a high-rise waist, a frayed cut-off hem, and a form-hugging fit. The trendy acid-wash denim fabric offers a moderate stretch. Style with a crop top and cowboy boots!

    Fit & Features

    • High-rise waist
    • Frayed cut-off hem
    • Front button, hidden zipper closure
    • Five-pocket and belt loop design
    • Acid-wash denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06603-0324

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Golden Hour Tie-Front Linen Vest

    Perfect for every day, you'll love the minimal vibes of this linen vest! The sleeveless lapel collar and tie-front closure add a modern aesthetic to any outfit, while the cropped hem finishes the chic look. Style with the matching pants.

    Shop Matching Bottoms: Golden Hour High-Rise Cargo Wide-Leg Linen Pants

    Fit & Features

    • Linen blend fabric, no stretch
    • Lapel collar neckline
    • Tie-front closure
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-1724

    Category Name: Vacation Looks

    Price: $14.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish And Edgy Cropped Denim Jacket

    Layer on this cool cropped denim jacket for a stylish and edgy look. It features a collared neckline, long sleeves, a complete button-down front, buttoned chest pockets, distressed detailing, and a cropped, frayed hem. Pair this jean jacket over your fave casual romper and complete the look with booties.

    Fit & Features

    • Collared neckline
    • Long sleeves, single-button details
    • Complete button-down front
    • Buttoned chest pockets
    • Denim fabric, distressed detailing
    • Cropped, frayed hem, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06203-0226

    Category Name: Vacation Looks

    Price: $16.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Treasure Linen Wide-Leg Pants

    Everyone will be asking where you found these trendy linen wide-leg pants! You'll love the high-rise waist offering a flattering fit, while the wide-leg silhouette gives off that effortlessly chic vibe. The waist is accented with pleating, dual front pockets, and a back zipper closure for a secure fit. Complete the look with the matching corset top!

    Shop Matching Top: Trendy Treasure Strapless Linen Corset Top

    Fit & Features

    • Linen-blend woven fabric, stretchy knit lining
    • High waist
    • Wide-leg silhouette
    • Pleating, back zipper and hook-eye closure
    • Dual front pockets
    • Back zipper
    • Runs true to size

    Style Number/Barcode: 06302-0814

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Splashin' Around Eyelet Ruffle Swim Shorts

    Splish-splash-looking flirty in these eyelet ruffle swim shorts perfect for pool parties, beach days, and vacations!

    Fit & Features

    • Eyelet fabric
    • High-rise elasticized waist
    • Ruffle trim
    • Runs true to size

    Style Number/Barcode: 07105-000001

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Daytime Cheer Fit And Flare Ruffle Floral Dress

    Spread daytime cheer in this fit and flare floral dress! Made from soft chiffon fabric, this dress is adorned with a ditsy floral print for a whimsical touch.  This playful dress features a sweetheart neckline with ruffle trim, adjustable spaghetti straps, and a charming keyhole bust tie. The stretchy smocked waist and tiered ruffled hem create a flattering fit and flare silhouette. Complete the look with a cute purse and sandals!

    Fit & Features

    • Ditsy floral print, chiffon fabric, stretchy knit lining
    • Ruffle trim sweetheart neckline
    • Adjustable spaghetti straps
    • Stretchy smocked waist
    • Fit and flare silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5447

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Style Icon Cutout Bodycon Midi Dress

    This sultry-chic midi dress will level up your look and make you a casual style icon! It features a sleeveless asymmetric one-shoulder neckline with a tank strap, a bold asymmetric waist cutout for a hint of skin, a midi-length hem, and a bodycon silhouette that will hug your curves. The ribbed knit fabric offers plenty of stretch. Pair with clear mules.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Tank strap
    • Asymmetric waist cutout
    • Midi-length hem
    • Bodycon silhouette
    • Stretchy ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5201

    Category Name: Vacation Looks

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Lovin' Crochet Knit Mini Dress

    You'll love the summer vibes this crochet knit mini dress brings to your happy hour look. Designed with a strapless neckline and sultry side slit, the bodycon fit will flaunt your stunning curves.

    Fit & Features

    • Sheer crochet knit fabric with knit lining, moderate stretch
    • Strapless straight-across neckline
    • Ruched side seam, adjustable drawstring, side slit
    • Mini-length asymmetric hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000046

    Category Name: Vacation Looks

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic And Elevated Trouser Shorts

    Refresh your wardrobe with these chic and elevated trouser shorts! They feature a high-rise waist, a front button closure, front pleated detailing, and a fitted silhouette. The smooth crepe fabric includes a woven lining. Style with the matching blazer.

    Shop Matching Ivory Blazer: Chic And Elevated Woven Blazer

    Shop Matching Pink Blazer: Bold Moves Woven Blazer

    Shop Matching Turquoise Blazer: Bold Moves Woven Blazer

    Fit & Features

    • High-rise waist
    • Front button, hidden button and zipper closure
    • Front pleating
    • Front pockets
    • Fitted
    • Crepe fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0263

    Category Name: Vacation Looks

    Price: $14.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacay Mood Strapless Tropical Knit Jumpsuit

    This eye-catching tropical knit jumpsuit will put you in the mood for a beachy vacay! Designed with a stretchy knit fabric with a multi-colored tropical print pattern, this jumpsuit will bring the bold allure to your dreamy getaway. It features a strapless straight-across neckline, a fitted high waist for a snatched look, and a relaxed wide-leg silhouette. Style with chunky gold hoops and strappy sandals.

    Fit & Features

    • Stretchy knit fabric, bust lining
    • Tropical print
    • Strapless straight neckline
    • Fitted high waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2454

    Category Name: Vacation Looks

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Way She Moves Striped Bra Top

    This striped bra top has entered the girl's vacay chat! Boasting a sexy plunge neckline and cutout back, you'll be the hit of the trip. Pair with the matching skirt to complete the look!

    Shop Matching Bottoms: Way She Moves Striped Midi Skirt

    Fit & Features

    • Striped print, scalloped trim, stretchy knit fabric
    • Plunge V-neckline
    • Wide shoulder straps
    • Cutout back with tie closure
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-2258

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Sweetheart Mesh Mini Dress

    You'll be such a stunning sweetheart in this gorgeous mesh mini dress! Featuring a flattering ruffled padded sweetheart neckline with an off-the-shoulder design and a curve-hugging fit with all-over ruched detailing, this dress is perf for your next date night with bae. Pair with some clear lucite heels for that it-girl look.

    Fit & Features

    • Off-the-shoulder neckline, short sleeve cuffs
    • Sweetheart neck, built-in padded bust
    • Ruffle trim detailing, all-over ruching
    • Back zipper and hook and eye closure
    • Short, form-hugging fit
    • Sheer mesh fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1539

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale