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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.

  • Flower Up Strapless Skater Dress

    Recharge your wardrobe by adding some bright floral prints! We know you'll be slaying it in the Flower Up skater dress. 

    Fits & Features

    • Elastic, Strapless Neckline 
    • Mini Length Silhouette I Skater Style Skirt 
    • Chiffon Fabric I Floral Print All Over 
    • Ruffle-Trim At Hem & Neckline
    • Form Hugging Fit 

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

    Style Number/Barcode: 05102-0418

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Live For The Lace Up Tube Top

    We live for the sexy lace up detail on this trendy tube top! Perf for the warmer months, pair with some denim cut offs and sneaks! Wear as a cross front halter as well for another cute look!

    Fit & Features

    • Lace front detail | Tie closure
    • Cropped
    • Knit fabric
    • Plenty of stretch
    • Form hugging fit

    Style Number/Barcode: 06001-2590

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Stunner Ruched Maxi Dress

    You'll be quite the stunner in this floral ruched maxi dress! Its stretchy knit fabric will hug and flatter your curves beautifully!

    Fit & Features

    • Spaghetti straps | Cross back
    • V neckline
    • Center ruched detailing
    • Front slit
    • Stretchy knit fabric
    • Floral print

    Style Number/Barcode: 05101-0073

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Picturesque Petals Tiered Ruffle Chiffon Mini Dress

    Feel and look picture-perf in this fun floral dress! Pair your look with a denim jacket and some white sneakers! 

    Fits & Features

    • Adjustable Spaghetti Straps
    • V Neckline I Square Sheer Back 
    • Drawstring Waist 
    • Mini Length Silhouette I Tiered Ruffle Trim Design 
    • Floral Chiffon Fabric I Fully Lined 
    • Zipper Not Featured

    Style Number/Barcode: 05102-0503

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Gal Lace Up Back Chiffon Floral A-Line Dress

    Special Occasion

    Glide along effortlessly in our beautiful Gal! Perfect for the springtime wedding guest, she's crafted from airy chiffon with beautiful rose print throughout. Features like her thigh-high slit let you show off your heels and dance throughout the night without any constrictions. Pair her with a crossbody clutch for a chic (and practical) touch! 

    Fits & Features

    • Buttoned Halter Straps 
    • Cross & Laces Up At The Back I Elastic Back Waistband
    • Plunging V Neckline I Padded Bust 
    • Floor Length Hemline I A-Line Silhouette 
    • Front Slit 
    • Fully Lined Chiffon Fabric I Floral Print 
    • Form Hugging Fit I Moderate Stretch 

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

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05002-0430

    Category Name: Vacation Looks

    Price: $31.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • A New York Minute Faux Leather Crossbody Purse

    Everything can change in a new york minute so, make sure ur ready with the essentials at your side! Strap this crossbody over a white tee to make it pop!

    • Medium rectangular structure
    • Faux leather
    • Quilted design
    • Golden turn lock closure
    • Convertible handle to crossbody strap
    • Inner zipper closure | Outer open pocket

    Style Number/Barcode: 07203-0279

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Which Way To The Beach Large Straw Tote

    Excuse me miss, which way to the beach? and where did you get that straw tote from? and that sweet summer style? 

    • Large over-sized U-shape structure
    • Double O-ring handles
    • Woven straw design
    • Cotton lining 
    • Drawstring closure

    Style Number/Barcode: 07203-0285

    Category Name: Vacation Looks

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flounce With Me Off Shoulder Tie Dye One Piece Swimsuit

    Girl, work it!! Get the party bouncin' in this swimsuit! Just make sure you add a pair of shades for a bomb lewk! 

    Fits & Features

    • One Piece Swimsuit 
    • Off Shoulder Ruffle Design 
    • Molded Padded Bust 
    • Open Back Design
    • Center Strap Connects To High Waisted Bottoms
    • Fully Lined I Tie Dye Print 

     

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

    Style Number/Barcode: 07109-0205

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sea Breeze Hipster Swim Bottoms

    Get ready to relax by the sea in these must have swim bottoms! Pick up the matching swim top to complete the look!

    Shop Matching Top: Sea Breeze Tie Front Swim Top

    Fit & Features

    • Hipster design
    • Cheeky bottom

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

    Style Number/Barcode: 07105-0570

    Category Name: Vacation Looks

    Price: $8.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sea Breeze Tie Front Swim Top

    Get ready to relax by the sea in this must have tie front swim top! Pick up the matching swim bottoms to complete the look!

    Shop Matching Bottoms: Sea Breeze Hipster Swim Bottoms

    Fit & Features

    • Tank-like shoulder straps
    • Tie front closure
    • Light padding

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

    Style Number/Barcode: 07104-0422

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Change My Mind Cat Eye Sunglasses

    Give them a little bit of 'tude when you step out in these polished sunnies! Pair them with an all black outfit, and an over-sized blazer!

    • Large design 
    • Cat eye frame
    • Dark black lenses

    Style Number/Barcode: 07008-0736

    Category Name: Vacation Looks

    Price: $5.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mamacita Baseball Cap

    Oh hayyyyy mamacita! This hat would go perf with all your casual OOTDs!

    • Traditional Baseball Cap Design
    • Adjustable Strapback 
    • Embroidered "Mamacita" Script 

    Style Number/Barcode: 07302-0179

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take Me To Margaritaville Tropical Swim Top

    We are so ready for a little vacay time when we see this swimsuit! Don't forget to pick up the matching swim bottoms and throw on some pink lipstick!

    Shop Matching Bottoms: Take Me To Margaritaville Tropical Swim Bottoms

    Fit & Features

    • Tie front design
    • Adjustable spaghetti straps
    • Removable padding
    • Moderate stretch
    • Tropical print

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

    Style Number/Barcode: 07104-0441

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take Me To Margaritaville Tropical Swim Bottoms

    We are so ready for a little vacay time when we see this swimsuit! Don't forget to pick up the matching swim top and throw on some pink lipstick!

    Shop Matching Top: Take Me To Margaritaville Tropical Swim Top

    Fit & Features

    • High rise fit
    • Tie front detail
    • Cheeky bottom
    • Removable padding
    • Moderate stretch
    • Tropical print

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

    Style Number/Barcode: 07105-0589

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Set For Vacay Tropical Floral Strapless Midi Dress

    You'll be set for vacay in this strapless knit midi dress featuring a large tropical floral print for a bold allure. The form-hugging silhouette will flaunt your gorgeous curves.

    Fit & Features

    • Sleek knit fabric with full-length knit lining, high stretch
    • Large tropical floral print
    • Strapless straight-across neckline, no-slip strip
    • Midi-length hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6097

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Stunning Tank Swim Top

    Get those simple yet stunning vibes in this minimal tank swim top! Pair with the matching bottoms for the perf beach ready look!

    Shop Matching Bottoms: Simply Stunning High Waist Swim Bottoms

    Fit & Features

    • Thin shoulder straps
    • Square neck and back
    • Removable padding

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

    Style Number/Barcode: 07104-0442

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Stunning High Waist Swim Bottoms

    Get those simple yet stunning vibes in these minimal high waist swim bottoms! Pair with the matching top for the perf beach ready look!

    Shop Matching Bottoms: Simply Stunning Tank Swim Top

    Fit & Features

    • High rise elastic banded waist
    • Cheeky bottom

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

    Style Number/Barcode: 07105-0590

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Luxe Satin Bucket Hat

    Live that luxe life with a hat as extra as you! Pair this beauty with a glam look to create a head-turning impression! 

    • Bucket Design 
    • Flexible Brim 
    • Satin Material 
    • Lined 

    Style Number/Barcode: 07302-0153

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bright And Sunny Hipster Swim Bottomsok

    We are inspired for the brighter days when look at this cute sunny swim suit! Perfect to accentuate that bronze tan of urs! Don't forget to pick up the matching top bb!

    Shop Matching Top: Bright And Sunny Twist Front Swim Top

    Fit & Features

    • Mid-rise fit
    • Tie-hips
    • Moderate stretch
    • Cheeky bottom

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

    Style Number/Barcode: 07105-0568

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bright And Sunny Twist Front Swim Top

    We are inspired for the brighter days when look at this cute sunny swim suit! Perfect to accentuate that bronze tan of urs! Don't forget to pick up the matching bottoms bb!

    Shop Matching Bottoms: Bright And Sunny Hipster Swim Bottoms

    Fit & Features

    • Molded padded cups
    • Double spaghetti straps
    • Caged double O-ring back
    • Tie straps
    • Wired

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

    Style Number/Barcode: 07104-0420

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 5 Pack Tie Dye Scrunchies Set

    Tie dye is coming back in a big way baybayy! And we couldn't be more excited about it. Easily style with a graphic tee and sneaks!

    • Set of five scrunchies
    • Two satin with wired bow detail
    • Three velvet
    • Stretchy

    Style Number/Barcode: 07006-0145

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Sleek Tube Hoop Earrings

    Keep a sleek finish with a staple pair of gold hoop earrings! They literally go with everything, and add a little something to those lazy bun dayzz.

    • Large tube design
    • Sleek gold finish
    • Omega closure
    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics and lingerie are considered final sale merchandise FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.  

    Style Number/Barcode: 07001-0453

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Straight Talk Jelly Double Strap Sandals

    Straight talk we are ready to chill out in these slides! Made out of a soft jelly material, and designed with a relaxing vibe, pair them with your swim or high waist shorts!

    • Open round toe
    • Double buckle straps
    • Slide on design
    • Soft silicone jelly

    Style Number/Barcode: 07404-0533

    Category Name: Vacation Looks

    Price: $11.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Time Off Linen High Waist Wide Leg Pants

    Reset and recharge bb girl! Treat yourself to some time off and escape to a resort! You're going to need a cute linen set for that trip 

    Shop Matching Top: Time Off Puff Sleeve Linen Crop Top 

    Fits & Features 

    • High Rise Smocked Waistband 
    • Flowy Wide Leg Openings 
    • Cotton Blend Linen Fabric 
    • Relaxed Fit
    • Matching Top Sold Separately 

    Style Number/Barcode: 06302-0132

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance