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.

  • Beachy Vibes Bell Sleeve Tie-Front Top

    This airy lightweight knit tie-front top gives off those effortless beachy vibes! It features a scoop neckline, a dual tie-front design, long flared bell sleeves, a cute scalloped front hem, and a mid-length, relaxed fit. The sheer knit fabric features a textured ribbed pattern. Layer over a basic bodysuit and style with light-wash denim.

    Fit & Features

    • Scoop neckline
    • Dual tie-front design, thin straps
    • Long bell sleeves
    • Scalloped front hem
    • Mid-length, relaxed fit
    • Sheer knit fabric, textured ribbed pattern, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06202-0400

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Daydream Butterfly Chain Belt

    Soft girl energy? Activated. This butterfly chain belt flutters right into your faves with dreamy layered charms and delicate movement—perfect for cinching your waist with a little fairycore flair.

    Fit & Features

    • Chain-link design
    • Small and large butterfly charm accents
    • Adjustable fit with lobster clasp closure

    Style Number/Barcode: 07301-000144

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Sangria Sunset Strapless Paisley Satin Crop Top

    The perfect paisley satin crop top to wear during sunset cocktail hour! Crafted from a silky satin fabric with a summery paisley print, this crop top elevates every outfit. It features a strapless neckline and stretchy smocked back, a flirty tie design, and a pointed cropped hem that flaunts your figure. Complete the look in denim jeans and strappy sandals.

    Fit & Features

    • Paisley print, satin fabric, no stretch
    • Strapless neckline
    • Tie back design, smocked back
    • Pointed cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2545

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Crush Flower Stud Earrings

    Major flower power energy happening here. These flower stud earrings add the perfect flirty touch to your everyday vibe—whether it’s jeans and a tee or your fave dress.

    Fit & Features

    • Dainty metal flower design
    • Center rhinestone embellishment
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000122

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Low Effort Luxe Retro Sunglasses

    Instant cool-girl mode: activated. These rectangular-shaped sunglasses are giving low-effort luxe with a sleek retro frame that pairs perfectly with chunky hoop earrings.

    Fit & Features

    • Rectangular-shaped design
    • Thin metal frame
    • Thin metal arms
    • Flexible nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000025

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Done In One Zip-Front Tie-Waist Denim Romper

    Designed to be your new favorite done in one piece, this denim romper offers a cute and flattering style year-round! It's designed with classic short sleeves and collar neckline, a zip-front closure, two flap pockets and side pockets for convenience, a tie-waist belt that cinches your waistline, and a form-hugging fit. Complete the look with sleek hoop earrings and your fave sneakers!

    Fit & Features

    • Denim fabric, slight stretch
    • Short sleeves and collar neckline
    • Zip-front closure
    • Two flap pockets, side pockets
    • Tie-waist belt 
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-0400

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Minimalist Moment Two-Pack Bracelet Set

    When your wrists need a glow-up. This two-pack bracelet set brings sleek, sculptural energy that’s perfect for stacking or wearing solo.

    Fit & Features

    • Two-pack bracelet set
    • High-shine metal material
    • Sleek, structured designs
    • Hinge clasp design

    Style Number/Barcode: 07003-000033

    Category Name: Vacation Looks

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lavish Leopard Print Palazzo Wide-Leg Pants

    Look lavish in these leopard palazzo pants boasting a mid-rise waist and wide-leg silhouette perfect for elevating your look. Style with a crop top and heels.

    Fit & Features

    • Smooth woven fabric, no stretch
    • Leopard print 
    • Elasticized mid-rise waist
    • Wide-leg pant
    • Pants in size small have an 11.5" front rise with a 28" inseam
    • Runs true to size

    Style Number/Barcode: 06402-1449

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bloom Baby Flower Claw Clip Set

    Hair game = bloomin’ cute. These floral claw clips bring the vibe, whether you're going for soft girl sweet or Y2K realness—just clip and go.

    Fit & Features

    • Durable material with a glossy finish
    • Bold floral design with petal detail
    • Claw grip closure 

    Style Number/Barcode: 07006-000057

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: NS

  • Everyday Cowgirl Colored Stone Straw Western Hat

    Top off your cowgirl core look with this straw western hat at bachelorettes, festivals, or country bar nights! Made from distressed straw material for a rustic feel.  Featuring a string tie bow adorned with a colorful stone and metal ball trim, this hat adds a touch of glam to the classic curved wide brim. Complete the look in cowboy boots.

    Fit & Features

    • String tie bow, colored stone and metal ball trim
    • Classic curved wide brim
    • Distressed straw material
    • Adjustable inner strings for a snug fit

    Style Number/Barcode: 07302-1604

    Category Name: Vacation Looks

    Price: $4.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Love Of Details V-Neck Lace-Up Skater Dress

    Fall in love with every chic detail of this lace skater dress sure to romance every room you walk into! With adjustable spaghetti straps and a flattering V-neckline, our dress features a lace-up mesh bodice and a playful skater silhouette. The asymmetrical ruffled trim adds a touch of flirty sophistication, making it the perfect for brides, birthday girls, or party guests! Complete the look with dainty earrings and heels.

    Fit & Features

    • Lace fabric line with stretchy knit
    • Adjustable spaghetti straps, V-neckline
    • Back zipper and hook-eye closure
    • Mesh lace-up bodice
    • Asymmetrical ruffles
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3436

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Breezy Sheer Lace Tie-Front Top

    Cute and breezy, this sheer floral lace top features a V-neck with a tie-front design and long fitted sleeves with flared hems. Style with denim shorts and sandals for a casual summer look.

    Fit & Features

    • Sheer textured floral lace fabric
    • V-neckline
    • Tie-front design
    • Long fitted sleeves, flared hems
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06202-000029

    Category Name: Vacation Looks

    Price: $29.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Shades Square Sunglasses

    Discover these trendy sunglasses perfect for any sunny day to keep your style on point! They feature a small square shape, tinted UV protective lenses, and comfortable arms and nose support. Complete the look with platform sneakers for a casual day out.

    Fit & Features

    • Small square shape
    • Tinted UV protective lenses
    • Comfortable arms and nose support

    Style Number/Barcode: 07008-1089

    Category Name: Vacation Looks

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty Blooms Floral Strapless Jumpsuit

    Soft, flowy, and effortlessly pretty—this strapless jumpsuit feels like your fave playlist on repeat. Wide-leg fit keeps it relaxed while the floral moment brings the charm to your vacay or weekend plans!

    Fit & Features

    • Floral print, soft and smooth knit fabric, moderate stretch
    • Strapless neckline
    • Fitted bodice
    • Flowy wide-leg fit
    • Runs true to size

    Style Number/Barcode: 06502-000038

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: M, L

  • Weekend Feeling Sleeveless Bubble Hem Mini Dress

    A sleeveless knit dress features a classic crew neckline, a form-hugging fit, and a trending drop waist seam with a bubble mini-length hem. Style with a denim jacket for casual plans.

    Fit & Features

    • Knit fabric, moderate stretch
    • Crew neckline
    • Form-hugging fit
    • Drop waist seam, bubble mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5873

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Golden Nights Halter Ruffle Romper

    Perfect for any occasion when you want to shine, this halter romper features a flattering form-hugging fit and playful ruffles that create movement with every step. Style with lace-up heels.

    Fit & Features

    • Smooth knit stretchy fabric, shorts lining
    • Halter plunge neckline, tie closure
    • Form-hugging fit
    • Ruffled mini hem
    • Runs true to size

    Style Number/Barcode: 06503-000062

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK, GREEN

    Available Size: S, M, L

    Product Badge:
    • Back In Stock
  • Reusable Gel Lift Pasties

    These gel bra pasties create the perfect lift and nipple coverage for a smooth look. The supportive sticky bra design with its adhesive interior gently lifts the breasts and perfectly covers the nipples for a seamless look. Wear these bra pasties underneath an open-back halter top or strapless cocktail dress with a smooth shapewear style for the ultimate flawless ensemble. Wear with a sleeveless top and a cute pair of denim for your next-day date.

    Fit & Features

    • One pair
    • Gel pasties
    • Reusable, can be worn up to 25 times
    • Provide smoothing, lifting, and supporting effects

     

    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: 07101-0272

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: NS

    Product Badge:
    • Best Seller
  • Casual Staple Ribbed Knit Bandeau Top

    This casual ribbed knit bandeau top is a staple style to have in your closet. Pair with your fave high-rise bottoms or layered under cute tops!

    Fit & Features

    • Stretchy ribbed knit fabric
    • Strapless straight neckline
    • Cropped hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 07109-000001

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: BLACK, WHITE

    Available Size: S/M, M/L

  • Stole Your Heart Charms Shield Sunglasses

    These shield sunglasses will steal your heart! They showcase side heart charms for a trendy vibe, oversized tinted lenses, rubber nose supports, and comfortable arms. Complete the look in a cute jumpsuit.

    Fit & Features

    • Shield style oversized tinted lenses
    • Side heart charms
    • Rubber nose supports
    • Comfortable arms

    Style Number/Barcode: 07008-1093

    Category Name: Vacation Looks

    Price: $5.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Seas The Day Pearl and Charm Statement Necklace

    Giving total mermaid-on-vacay energy—and we’re obsessed. This pearl and charm necklace brings soft glam with a splash of beachy vibes, perfect for brunch plans or sunset selfies.

    Fit & Features

    • Faux pearl and charms
    • Long chain
    • Lobster clasp closure

    Style Number/Barcode: 07002-000143

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Adorable Chic Bow Cutout Bodycon Mini Dress

    Adorable chic and ready to be seen, this sleeveless mini dress is everything! It features adjustable spaghetti straps for a customizable fit, a sweetheart neckline adorned with a statement bow, and a cutout bust to show a peak of skin along the bodycon silhouette. Complete the look in high heels.

    Fit & Features

    • Smooth knit fabric lined with knit
    • Adjustable spaghetti straps
    • Sweetheart neckline with bow
    • Cutout bust
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-5697

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Finishing Touch Woven Shoulder Bag

    Put the perfect finishing touch to your look with this woven shoulder bag! With versatile styling options and a secure magnetic closure, you'll adore this bag all spring and summer.

    Fit & Features

    • Top shoulder strap
    • Detachable crossbody strap
    • Front flap with magnetic closure
    • Spacious interior
    • Woven faux leather material

    Style Number/Barcode: 07203-2130

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Golden Hour Shell Toe Ring Set

    Serving seaside glam with zero sand required. This 3-piece shell ring set brings the beach to your fingertips—literally. Stack 'em, mix 'em, or wear solo for a subtle flex.

    Fit & Features

    • Starfish, cowrie, and conch shell charms
    • Coastal-inspired accents
    • Pack includes three toe-rings

    Style Number/Barcode: 07004-000032

    Category Name: Vacation Looks

    Price: $6.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Kellie Strapless Ruffled Slit Lace Formal Dress

    Special Occasion

    A showstopping lace formal dress that exudes romance and modern elegance. Designed with a high strapless neckline, this long dress boasts a bodycon silhouette with flirty cascading ruffles and a sultry high-side slit. Complete the look with earrings and heels.

    Unapologetically bold, this dress is all about confidence. Keep the luxe look going with our stunning strapless prom dresses or discover the perfect fit among our stylish wedding guest dresses.

    Fit & Features

    • Lace fabric lined with stretchy knit
    • High strapless neckline, non-slip grip lining
    • Side zipper and hook-eye closure
    • High-side slit
    • Bodycon silhouette
    • Long-length hem
    • Runs true to size

    Style Number/Barcode: 05002-8961

    Category Name: Vacation Looks

    Price: $64.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, M, L