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.

  • Classic Everyday Style Thong Sandals

    These classic thong sandals are perfect for everyday wear during the warmer months! They feature an almond-shaped toe with a thin thong strap design, a flat sole, and an open back for easy on-and-off styling. Pair these sandals with hoop earrings for a simple yet chic vibe.

    Fit & Features

    • Almond-shaped toe
    • Thin faux leather thong straps
    • Flat sole
    • Open back
    • Faux leather insole
    • Runs true to size

    Style Number/Barcode: 07404-1087

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Girl Crepe Tie-Front Top

    Show your love for floral in this crepe crop top featuring three-quarter-length kimono sleeves, a plunge V-neckline, and a tie-front closure. Complete your cute look in new denim bottoms.

    Fit & Features

    • Three-quarter-length kimono sleeves
    • Plunge V-neckline
    • Tie-front closure
    • Cropped hem
    • Ditsy floral print
    • Crepe woven fabric
    • Runs true to size

    Style Number/Barcode: 06204-1405

    Category Name: Vacation Looks

    Price: $11.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Quilted Cutie Mini Crossbody Tote Bag

    Create a cute look for day dates and soirees accessorizing with this mini crossbody tote bag! It features a ruched top handle, detachable chain link strap, front flap with turn lock closure, quilted faux leather material, and a spacious interior to keep your must-haves in. Complete the look with fringe earrings.

    Fit & Features

    • Mini crossbody tote
    • Ruched top handle
    • Detachable chain link strap
    • Front flap, turn lock closure
    • Quilted faux leather material
    • Spacious lined interior

    Style Number/Barcode: 07203-1169

    Category Name: Vacation Looks

    Price: $5.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hide Out Square Oversized Sunglasses

    When you want to be under the radar, these oversized sunglasses are perfect for keeping low-key! They feature square-tinted lenses, rubber nose supports, and trendy chain link arms. Complete the look in a casual jacket for a coffee run.

    Fit & Features

    • Oversized style
    • Square tinted lenses
    • Rubber nose supports
    • Chain link arms

    Style Number/Barcode: 07008-0982

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Bold Dragon Print Cropped Tee

    Create a trendy bold look with this printed cropped tee that slays! It features a crew neckline, short sleeves, a cropped hem, a thin strappy design that ties at the waist, and an all-over dragon print pattern. The soft brushed knit fabric offers plenty of stretch. Style with faux leather shorts and heels!

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Fitted, cropped hem
    • Thin strappy design at the waist, tie closure
    • Dragon print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06002-1522

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Freshly Picked Floral Skater Dress

    Freshly picked from the garden. This floral skater dress is ready for your springtime festivities! It features short puff sleeves, a sweetheart neck with a tie-front closure, an open lace-up back design, and a tiered ruffled short-length hem. Complete the look in trendy new mules.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neck, tie-front closure
    • Open lace-up back design
    • Skater silhouette
    • Tiered ruffle short-length hem
    • Watercolor floral print, non-stretch fabric, woven lining
    • Runs true to size

    Style Number/Barcode: 05102-4993

    Category Name: Vacation Looks

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Sunshine Mesh Crop Bustier

    Embrace the sunshine in this floral mesh bustier perfect for the warmer season ahead! It features a sleeveless sweetheart neck, ruched bust, tank-style straps, a low square-cut back, and a cropped hem. Complete the look in a flirty mini skirt for a day date!

    Fit & Features

    • Sleeveless sweetheart neck, tank-style straps
    • Ruched bust
    • Low square-cut back, zipper and hook-eye closure
    • Cropped hem
    • Floral print mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4589

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Everyday Sparkle Rhinestone Strappy Sandals

    Add some sparkle to your everyday look with these trendy-glam sandals. They feature an open almond toe, an asymmetric strappy design with mini rhinestone embellishments, an adjustable ankle strap, and a low block heel. Style with a cute handbag.

    Fit & Features

    • Open almond toe
    • Asymmetric strappy design, mini rhinestones
    • Adjustable ankle strap, buckle detail
    • Low block heel
    • Faux leather material
    • Cushioned insole
    • Runs true to size

    Style Number/Barcode: 07404-1077

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Studded Western Buckle Belt

    Accessorize your music festival 'fits with this chic studded western buckle belt for a stylishly-edgy look. It features an outline of sleek studs and a large buckle with etched edges. Pair with distressed denim shorts.

    Fit & Features

    • Studded outline
    • Large metal buckle
    • Etched edges
    • Faux leather material

    Style Number/Barcode: 07301-0605

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Western Vibes Double Buckle Belt

    This festival season, show off chic western vibes when you accessorize your 'fits with this trendy belt! It features an adjustable double buckle design with etched detailing. Style with cowboy boots.

    Fit & Features

    • Adjustable metal double buckle design
    • Etched detailing
    • Faux leather material

    Style Number/Barcode: 07301-0604

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Grecian Mystique Bejeweled Flat Sandals

    Unlock a Grecian mystique allure in these flat patent sandals for your next getaway! They feature an almond toe, PVC clear caged straps with statement rhinestone jewels, and an adjustable ankle chain with lobster clasp closure. Complete the look in a chic sundress for a sunset dinner.

    Fit & Features

    • Almond toe
    • PVC clear caged straps
    • Statement rhinestone jewels
    • Adjustable ankle chain with lobster clasp closure
    • Patent leather footbed
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1123

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ethereal Glam Hair Claw Clip Set

    Enchant with an ethereal glam look with these stunning hair claw clips! The set features two clips, including one curved design with dainty chains and faux pearl beads, and one butterfly design with cascading snake chains and butterfly-shaped accents. Style with rhinestone stud earrings.

    Fit & Features

    • Two-pack metal claw clip set
    • Curved design, dainty chains and faux pearl beads
    • Butterfly design, snake chains and butterfly accents

    Style Number/Barcode: 07006-0394

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Full Bloom Floral Mesh Duster

    Layer on this fresh blooming floral mesh duster for a classic springtime look! It features long fitted sleeves, an open front, a long-length hem with a relaxed fit, and a beautiful floral print pattern. The sheer mesh fabric offers plenty of stretch. Style with a basic bodysuit and light wash denim.

    Fit & Features

    • Long fitted sleeves
    • Open front
    • Long-length hem, relaxed fit
    • Floral print
    • Sheer mesh fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06202-0375

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dinner And Drinks Halter Ruffle Romper

    Create sultry flair in this halter ruffle romper for your next date night or GNO! This romper is designed to show off with a plunge halter neckline and a short ruffled hem.

    Fit & Features

    • Smooth knit stretchy fabric
    • Plunge halter neckline with button closures
    • Partial open back
    • Ruffled short-length hem
    • Shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-1279

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Perfect Bow Linen Strapless Mini Dress

    Look like a gift of fashion in this perfect bow linen dress for a chic wedding reception or party look! Featuring a strapless neckline with non-slip grip lining, a center front bow, a bodycon silhouette, and a flirty hem slit. Complete the look with cute block heels.

    Fit & Features

    • Strapless neckline, non-slip grip lining
    • Center front bow
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Mini-length hem with slit accent
    • Double-lined linen fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2419

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keeper Of My Heart Rhinestone Three Ring Set

    You're the keeper of your heart! Flaunt your love for glamour with this three-pack ring set featuring one statement rhinestone heart ring, one heart outline ring, and one metal bead heart ring with dainty rhinestone embellishments. Style with an oversized blazer to complete your chic look!

    Fit & Features

    • Three-pack ring set
    • One statement heart rhinestone ring
    • One heart outline ring
    • One metal bead heart ring, dainty rhinestone embellishments

    Style Number/Barcode: 07004-0325

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Boho Print Halter Crop Top

    Show your sultry side in this boho print crop top perfect for festival babes! It features a sleeveless plunge halter neckline, tie-neck closure, open-back, and a smocked hem on non-stretch woven fabric. Complete the look in high-rise denim shorts.

    Fit & Features

    • Sleeveless plunge halter neckline
    • Tie-neck closure
    • Open back
    • Smocked crop hem
    • Boho challis print
    • Non-stretch woven fabric
    • Runs true to size

    Style Number/Barcode: 06003-1949

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Major Halter Lace-Up Denim Jumpsuit

    Elevate your style to major-trendsetter status! This denim jumpsuit is perfect for being seen around town. It features a sleeveless square neckline with halter straps, an open lace-up back with tie closure, front pockets, and a hip-hugging fit with a flared hem. Complete the look with an edgy choker.

    Fit & Features

    • Sleeveless square neckline with halter straps
    • Open lace-up back, tie closure
    • Front pockets
    • Hip-hugging fit
    • Flared hem
    • Dark wash denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06602-0335

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 90s Glam Rhinestone Beaded Denim Shorts

    Bring the 90s back in glamorous fashion! These denim shorts feature a flattering high-rise waist, front rhinestone beading along the pockets, and a form-hugging silhouette with a cut-off frayed hem. The shorts are composed of vintage-inspired medium-wash denim fabric with minimal stretch. Style with a cute bodysuit and sandals to complete the look!

    Fit & Features

    • High-rise waist
    • Front rhinestone beading along pockets
    • Form-hugging silhouette, cut-off frayed hem
    • Front five-button fly closure
    • Five-pocket styling, belt loop accents
    • Medium wash denim, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06603-0342

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Who's That Girl Rhinestone Chain Bra

    Who's that girl? It's you looking stunning in this bra perfect for festivals or Vegas! Featuring a sweetheart neckline, adjustable spaghetti straps, a padded underwire bra top with rhinestone and faux pearl pattern, cascading rhinestone strands that are detachable, and back hook and eye closures. Complete the look in a sultry mid-rise mini skirt.

    Fit & Features

    • Sweetheart neckline, adjustable spaghetti straps
    • Padded and underwire bra top
    • Rhinestone and faux pearl patterns on cups
    • Cascading and detachable rhinestone strands
    • Back hook and eye closures
    • Lined smooth woven fabric
    • Runs true to size

    Style Number/Barcode: 06003-2165

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On Deck Carpenter Cargo Denim Jeans

    Get your streetwear style on deck! Kick it in these cool carpenter denim jeans featuring a high-rise waist, wide-leg silhouette, utility-inspired cargo six-pocket styling, and are composed of non-stretch denim fabric. Complete the look in a corset top for a day out with friends!

    Fit & Features

    • High-rise waist
    • Wide-leg silhouette
    • Utility cargo six-pocket styling
    • Front button and hidden zipper closure
    • Belt loop accents
    • Non-stretch denim fabric
    • Runs true to size

    Style Number/Barcode: 06602-0409

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Mart Chiffon Skater Dress

    Always look like you've just come from somewhere with flowers! This breezy ditsy floral skater dress embodies every girl's favorite thing about spring. It features sheer 3/4 length sleeves with elastic cuffs, a sweetheart neck with a bust tie and keyhole, a smocked back, and a flowy fit and flare short-length hem. Complete the look in platform wedges.

    Fit & Features

    • Sheer 3/4 length sleeves, elastic cuffs
    • Sweetheart neck, bust tie, and keyhole
    • Smocked back
    • Skater silhouette, short-length hem
    • Ditsy floral print
    • Chiffon fabric with lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2161

    Category Name: Vacation Looks

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet As Can Be Lace Midi Dress

    Look and feel sweet as can be in this lace midi dress for a chance at romance! Features adorable short puff sleeves, a sweetheart neckline, a form-hugging silhouette, a flirty front slit, and a slight flare hem. Style with heeled sandals for a cute look for day dates and brunch!

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline
    • Back zipper and hook-eye closure
    • Form-hugging silhouette
    • Front slit, slight flare midi-length hem
    • Lace fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2020

    Category Name: Vacation Looks

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Daze Eyelet Tie Mini Dress

    If you've got sunshine on your mind, this eyelet mini dress is the one you want for those warmer days ahead. Featuring an off-the-shoulder ruffle neckline, short sleeve cuffs and spaghetti straps, a bust tie front design, and a bodycon silhouette. Complete the look in cute sandals for a family picnic!

    Fit & Features

    • Off-the-shoulder ruffle neckline
    • Short sleeve cuffs, spaghetti straps
    • Bust tie front design
    • Bodycon silhouette
    • Mini-length hem
    • Eyelet knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4908

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale