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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.

  • Crochet Fringe Hem Crop Top

    This cute crop top perfectly shows off your bralette, bandeau or swim top in a subtly chic way! Perfectly pair this with high waisted denim shorts for a beach day or top this onto your festival 'fit! 

    Fits & Features 

    • Crew Neckline
    • Long Sleeves
    • Crop, Fringe Hemline 
    • Crochet Net Fabric 
    • Relax Fit I Moderate Stretch 

    Style Number/Barcode: 06005-0350

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Fun Tie Back Skater Dress

    Look absolutely sweet and chic in this floral skater dress! It's the perfect attire for brunch with your girls or the upcoming baby and bridal showers! 

    Fits & Features

    • Spaghetti Straps
    • Square Neckline 
    • Tie Back I Low Open Back
    • Mini Length Hem I Skater Style Silhouette
    • Knit Fabric I Fully Lined I Floral Print 
    • Moderate Stretch 

    Style Number/Barcode: 05101-0408

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Own It Molded Swim Top

    Work it bb girl! Look absolutely killer in this sexy swim suit. Make sure you grab those matching bottoms before you check out! 

    Shop Matching Top: Own It Hipster Swim Bottoms

    Fits & Features

    • Wide Adjustable Straps With Metal Eyelet Design 
    • Back Metal Bar Clasp Closure
    • Molded Padded Ribbed Bust
    • Matching Bottoms Sold Separately 

    Model is 5'4" with a 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

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

    Style Number/Barcode: 07104-0425

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Neon Drama Lace Up Swimsuit

    Make a major bold statement poolside in this vibrant neon lace up swimsuit! Pair with some oversize sunnies and get ready to serve some sass!

    Fit & Features

    • Spaghetti straps that lead to a halter neck | Tie closure
    • Partial lace up front | Tie closure
    • Front cut out
    • Tie back detail
    • Lace up details on each side
    • High rise fit | Cheeky bottom

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

    Style Number/Barcode: 07109-0203

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Beachside Babe Lace Up One Piece Swimsuit

    Girls just wanna have sun  Soak up the fun in your new fave one-piece! All you need is a pair of cat sunnies for a beach-ready lewk. 

    Fits & Features

    • Halter Tie
    • Plunging V Neckline I Removable Padded Bust
    • Lace-Up Detail At Center Bodice & Side Hips 
    • Low Scoop Back
    • Cheeky Coverage Bottoms 

     

    Model is 5'4" with a 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

     

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

    Style Number/Barcode: 07109-0202

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cut Out For This One Shoulder Swimsuit

    Ooh girl, a look cut-out for those night swims! Make waves in this bold and bright swimsuit. 

    Fits & Features

    • One Piece Swimsuit 
    • One Shoulder Strap
    • Bandeau-Style I O-Ring At Center Front I Metal Clasp At Back
    • Removable Padded Bust
    • Cut Out Design 
    • Cheeky Coverage Bottoms 

     

    Model is 5'4" with a 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

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

    Style Number/Barcode: 07109-0204

    Category Name: Vacation Looks

    Price: $14.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Playing Nice Floral Smocked Swim Top

    Play nice this weekend in the cutest swim suit of the season! Smocked, and floral, what more can you ask for? Don't forge to pick up your matching swim bottoms!

    Shop Matching Bottoms: Playing Nice Floral Tie Swim Bottoms

    Fit & Features

    • Square neckline
    • Self tie spaghetti straps 
    • Cropped hemline 
    • Removable padding
    • Smocked bodice
    • Bright ditsy floral print

    Model is 5'8" with 34" bust, 24" waist and 37" hips. She is wearing a size small.  

    Style Number/Barcode: 07104-0462

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Then Sour Lemon Swim Top

    Are you sweet or sour? Lay out poolside in the cutest lemon print swim suit, and sip that lemonade! Don't forget to pick up your matching swim bottoms!

    Shop Matching Bottoms: Sweet Then Sour Lemon Swim Bottoms

    Fit & Features

    • Deep V-neckline
    • Tank straps
    • Strappy chest detail
    • Bar hook closure
    • Removable padding
    • Lemon print pattern

    Model is 5'8" with 34" bust, 24" waist and 37" hips. She is wearing a size small.  

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

    Style Number/Barcode: 07104-0463

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Unforgettably Sweet Floral Bodycon Ruffle Mini Dress

    Create an alluring look in this floral mini dress in a bodycon fit with a flirty ruffled hem. Perfect for shower celebrations and graduations!

    Fit & Features

    • Floral print, lace-lined fabric
    • Strapless neckline
    • Bodycon silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5985

    Category Name: Vacation Looks

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Playing Nice Floral Tie Swim Bottoms

    Play nice this weekend in the cutest swim suit of the season! Smocked, and floral, what more can you ask for? Don't forge to pick up your matching swim top!

    Shop Matching Top: Playing Nice Floral Smocked Swim Top

    Fit & Features

    • Low rise front
    • Cheeky bottom
    • Self tie hips
    • Bright ditsy floral print

    Model is 5'8" with 34" bust, 24" waist and 37" hips. She is wearing a size small.  

    Style Number/Barcode: 07105-0609

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island In The Sun Bow Front Swim Top

    Get caught under the rays in a sweet striped swim suit! Pair with bright orange lipstick and live your best life! Don't forget to pick up your matching swim bottoms!

    Shop Matching Swim Bottoms: Island In The Sun Bow Front Swim Top

    Fit & Features

    • Sweetheart neckline
    • Tie front detail
    • Halter tie spaghetti straps
    • Striped pattern
    • Lined | Removable padding
    • Moderate stretch

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

    Style Number/Barcode: 07104-0460

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island In The Sun Striped Swim Bottoms

    Get caught under the rays in a sweet striped swim suit! Pair with bright orange lipstick and live your best life! Don't forget to pick up your matching swim top!

    Shop Matching Top: Island In The Sun Bow Front Swim Top

    Fit & Features

    • High waist swim bottoms
    • Cheeky bottom
    • Striped pattern
    • Lined
    • Moderate stretch

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

    Style Number/Barcode: 07105-0607

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Twist It Out Swim Bottoms

    Give your a look a twist this season with this vibrant piece that is perf for your next vacation! Pair these bottoms with the matching top for the perf look! 

    Shop Matching Top: Twist It Out Swim Top

    Fit & Features

    • High Rise Waist
    • Waist Cut Out
    • Twist Front Accent 
    • Cheeky Bottom 

     

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


    Style Number/Barcode: 07105-0572

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Good Vibes Only Hipster Swim Bottoms

    You'll bring only the good vibes in these simple & sexy swim bottoms! Pair with the matching top for an all togther gorgeous look.

    Shop Matching Top: Good Vibes Only Lace Front Swim Top

    Fit & Features

    • Hipster style design
    • Cheeky bottom
    • Ribbed fabric

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

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

    Style Number/Barcode: 07105-0604

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Good Vibes Only Lace Front Swim Top

    You'll bring only the good vibes in this simple & sexy swim top! Pair with the matching bottoms for an all togther gorgeous look.

    Shop Matching Bottoms: Good Vibes Only Hipster Swim Bottoms

    Fit & Features

    • Adjustable halter strap | Strap is removable
    • Lattice front | Tie closure
    • Back tie closure
    • Removable padding
    • Ribbed fabric

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

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

    Style Number/Barcode: 07104-0457

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fringe Benefits Swim Bottoms

    Fringe is one trend you'll want to commit to this season! Work on that glow in these fierce fringe swim bottoms! Don't forget to pick up the matching top! 

    Shop Matching Top: Fringe Benefits Bikini Top

    Fit & Features

    • Mid Rise Fit 
    • Hipster Fit 
    • Fringe Trim 
    • Cheeky Bottom 
    • Moderate Stretch 

     

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

    Style Number/Barcode: 07105-0602

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Just Add Water High Waist Swim Bottoms

    Girl, it's about time you pack your bags and head somewhere warm! Just make sure you pick up the matching swim top to complete these bottoms!

    Fits & Features

    • High Waist Fit 
    • Adjustable Tie Sides 
    • Fully Lined 
    • Moderate Stretch
    • Matching Top Sold Separate 

     

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

    Style Number/Barcode: 07105-0574

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Salt & Sun Tie Side Hipster Swim Bottoms

    All you need is the sun and sea...andddd this bomb swim set! Just make sure you add the matching bottoms to cart and some cute sunnies while you're at it 

    Shop Matching Top: Salt & Sun Lace Up Racerback Swim Top

    Fits & Features

    • Hipster-Style Swim Bottoms
    • Lace-Up Side Details 
    • Cheeky Fit & Coverage
    • Fully Lined 
    • Matching Top Sold Separate 

    Model is 5'4" with a 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

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

    Style Number/Barcode: 07105-0575

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sun Rays Tropical V-Neck Babydoll Mini Dress

    Flaunt beachy perfection in this tropical babydoll dress with a strappy tie-back that turns heads with every wear! Style with sandals for a cute vacation look.

    Fit & Features

    • Tropical print, woven fabric, bust knit lining
    • V-neckline, twisted bust
    • Spaghetti straps
    • Strappy tie-back design
    • Babydoll silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000042

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sun Lovin' Buckle Waist One Piece Swimsuit

    Here for the fun and here for the sun! The perf swimsuit for kickin' it poolside and slaying it. Don't forget to top it off with some cute sunnies! 

    Fits & Features

    • One Piece Swimsuit 
    • Wide Shoulder Straps
    • Plunging V Neckline At The Front & Back I Removable Padded Bust
    • Ruching At The Sides 
    • Removable Matching O-Ring Belt 
    • Cheeky Bottoms 

    Model is 5'4" with a 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

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

    Style Number/Barcode: 07109-0200

    Category Name: Vacation Looks

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Salt & Sea Lace Up Racerback Swim Top

    All you need is the sun and sea...andddd this bomb swim set! Just make sure you add the matching bottoms to cart and some cute sunnies while you're at it 

    Shop Matching Bottoms: Salt & Sun Tie Side Hipster Swim Bottoms 

    Fits & Features

    • Wide Shoulder Straps
    • Adjustable Lace-Up Design At The Racerback 
    • Molded & Padded Cups
    • Decorative Knot Front 
    • Matching Bottoms Sold Separate 

    Model is 5'4" with a 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

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

    Style Number/Barcode: 07104-0427

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fresh Start Floral Off Shoulder Dress

    Spring is here and it's time for a fresh start on that wardrobe! Wear this gorgeous chiffon dress out for all those sunny affairs! 

    Fits & Features

    • Off Shoulder Elastic Neckline & Long Sleeves
    • Elastic Cuffs 
    • Mini Length Silhouette 
    • Chiffon Fabric | Full Knit Lining 
    • Floral Print Design 
    • Moderate Stretch 

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0450

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Glow Up Hipster Swim Bottoms

    You'll totally glow girl in these hipster swim bottoms! Pair with the matching lace front swim top and get ready to own that beach!

    Shop Matching Top: Glow Up Lace Front Swim Top

    Fit & Features

    • Hipster design
    • Side tie closures
    • Cheeky bottom
    • Fabric has slight sheen

    Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

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

    Style Number/Barcode: 07105-0601

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Luxe Lurex Knit Pants

    Get cozy in the luxe lurex knit pants. With a mid-rise drawstring waist and straight-leg fit, these pants are your go-to for effortless style and comfort.

    Fit & Features

    • Lurex knit fabrication
    • Mid-rise waist
    • Drawstring waist
    • Straight-leg fit
    • Runs true to size

    Style Number/Barcode: 06502-2556

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free