Vacation Looks

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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.

  • High-Rise Destructed Boyfriend Jeans

    Give your casually chic outfits an edgy aesthetic with these deconstructed high-rise jeans. These boyfriend-fit medium-wash denim jeans have the perfect amount of ripped detailing at the knees with a straight-leg silhouette for an absolutely on-trend look. Pair these high-waist ripped jeans with a cute crop top and chunky sneakers for day or a sparkly bustier with strappy heels for a sexy night look.

    Fit & Features

    • High-rise waist
    • Boyfriend style leg
    • Distressed detailing, slits at the knees
    • Multi button-down front closure
    • Five-pocket and belt loop design
    • Medium wash denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06602-0184

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feeling Breezy Crochet Bolero Sweater

    Layer on this crochet bolero sweater for an effortlessly breezy, cute look! 

    Fit & Features

    • Sheer crochet fabric
    • Long sleeves with flare cuffs
    • Open front design
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-000051

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: TAN

    Available Size: XS, S, M, L

  • 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
  • Outside The Lines Floral Print Crop Top

    Style outside the lines and go for a bold chic look in this floral print crop top. Style with the matching skirt for a complete look.

    Shop Matching Skirt: Outside The Lines Floral Print Maxi Skirt

    Fit & Features

    • Bold floral print, lined stretchy knit fabric
    • Strapless
    • Ultra crop-length hem
    • Runs true to size

    Style Number/Barcode: 06001-5658

    Category Name: Vacation Looks

    Price: $19.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

  • 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
  • Strut It Out Abstract Zebra Maxi Skirt

    Perfect your vibe with the strut it out abstract zebra maxi skirt. This sheer mesh beauty flaunts a zebra print and mid-rise waist for a fierce look. Pair it with the matching top for ultimate style.

    Fit & Features

    • Sheer mesh fabrication lined with stretchy knit
    • Mid-rise waist
    • Zebra print
    • Maxi length hem
    • Runs true to size


    Shop Matching Top: Strut It Out Abstract Zebra Tie-Front Top

    Style Number/Barcode: 06501-1105

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • 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: 05102-6094

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • Catch My Sweetness Halter Floral Corset Top

    Everyone will catch your sweet vibe in this eyelet floral corset top with a sultry plunge halter neckline and flexible boning that snatches your waist.

    Fit & Features

    • Floral print, eyelet woven-lined fabric
    • Plunge halter neckline, tie-back straps
    • Stretchy smocked back
    • Flexible boning
    • Hidden front hook and eye closures
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000005

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

    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
  • 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
  • Set The Tone Halter A-Line Floral Midi Dress

    Set the tone for spring dressing in this halter floral midi dress designed in a statement A-line silhouette perfect for brunch, garden parties, and day dates!

    Fit & Features

    • Floral print, woven fabric, woven lining
    • Sweetheart halter neckline, tie-back design
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Flowy midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3969

    Category Name: Vacation Looks

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • Laid Back Fave Crew Neck Tank Maxi Dress

    Your new laid-back fave tank maxi dress for styling up or down for any occasion! Crafted from rib knit fabric, this crew neck dress offers a form-hugging fit and a maxi-length hem for a flattering silhouette. Complete the look in cute sandals and sunnies!

    Fit & Features

    • Rib-knit stretchy fabric
    • Crew neck
    • Form-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5573

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • 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
  • All About Summer Crochet Halter Top

    This summer, it's all about breezy lightweight fabrics like this trendy crochet halter top. It features a tie-back halter neckline and cropped, curved hanky hem perfect for pairing with denim shorts.

    Fit & Features

    • Crochet cotton fabric, partial stretch, cotton lining
    • Sleeveless halter neckline, tie-back straps
    • Partially open back
    • Cropped curved hanky hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-000050

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • 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
  • Tropical Lifestyle Floral Halter Mesh Crop Top

    Let sunshine days be filled with sand and compliments when you step out in this floral halter crop top. Perfect for vacations or staycations!

    Fit & Features

    • Floral print, mesh-lined fabric
    • Halter cowl neckline, tie strap
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000061

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

  • 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