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.

  • Favorite Pick Ruched Slit Midi Dress

    Your new favorite midi dress for looking stylish and cute! It features a sleeveless square neck, sleek bungee spaghetti straps, a bodycon silhouette, and a side slit with a ruched drawstring that lets you customize the fit. The midi dress is composed of a rib-knit fabric with lining and plenty of stretch. Complete the look in trendy flat sandals for a bridal shower or brunch! 

    Fit & Features

    • Sleeveless square neck
    • Bungee spaghetti straps
    • Bodycon silhouette
    • Side slit, ruched adjustable drawstring
    • Midi-length hem
    • Rib knit-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5034

    Category Name: Vacation Looks

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bohemian Dreamer Sweater Knit Halter Top

    Create a dreamy bohemian-inspired look with this sweater knit crop top. It features a sleeveless halter neckline with spaghetti straps, an open back with cross-back straps and a lower lace-up strappy design, and a fitted, cropped hem with a dainty eyelet pattern. Style with a printed maxi skirt and strappy sandals.

    Fit & Features

    • Sleeveless halter neckline
    • Spaghetti straps
    • Open back, cross-back straps
    • Lower lace-up strappy design, tie closure
    • Fitted, cropped hem, eyelet pattern
    • Ribbed sweater knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1445

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Girl Era Chunky Platform Mules

    You'll be in your trendy girl era with these fabulous chunky platform mules! They feature an open almond-shaped toe, a wide banded toe strap, an open back for easy on-and-off styling, a chunky platform with a lug sole, and a tall block heel. Style with a flirty floral dress.

    Fit & Features

    • Open almond-shaped toe
    • Wide banded toe strap
    • Open back
    • Chunky platform, lug sole
    • Tall block heel
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-4200

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Total Glam Vibe Rhinestone Lace-Up Sandals

    Give off a total glam vibe in these rhinestone lace-up sandals that will add a trendy sparkle! They feature an almond-shaped toe with a strap, an asymmetric strappy design that laces up the leg with mini rhinestone embellishments, and a comfortable flat sole. Style with a graphic tee and distressed denim shorts for an edgy look.

    Fit & Features

    • Almond-shaped toe, toe strap
    • Asymmetric strappy lace-up design, tie closure
    • Mini rhinestones
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1135

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Country Style Western Denim Booties

    Amp up your looks for festival season or every day with this trendy pair of western denim booties! They feature a mid-calf height with loops on each side for easy on-and-off styling, an inner zipper closure, a pointed toe, a comfortable stacked block heel, and cute western-inspired stitching with a side pocket detail. Style with a casual dress and hoop earrings!

    Fit & Features

    • Mid-calf height
    • Loop accents, inner zipper closure
    • Pointed toe
    • Stacked block heel
    • Denim fabric
    • Western-inspired stitching, side pocket detail
    • Runs true to size

    Style Number/Barcode: 07403-1636

    Category Name: Vacation Looks

    Price: $18.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Diva Alert Denim Platform Block Heels

    These diva-worthy denim platform block heels will level up all of your fab 'fits! They feature an open almond-shaped toe with a strap, a thin adjustable ankle strap, a bold platform sole, and an ultra-tall block heel. Style with a trendy shoulder bag.

    Fit & Features

    • Open almond-shaped toe
    • Toe strap
    • Thin adjustable ankle strap, buckle detail
    • Platform sole
    • Ultra-tall block heel
    • Denim material
    • Runs true to size

    Style Number/Barcode: 07401-4279

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Basic Ribbed Knit Crop Top

    Keep it stylish in basics! This versatile crop top features a sleeveless square neckline, bungee spaghetti straps, and a cropped hem. The top is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with high waist shorts and a floppy hat

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Cropped hem
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0976

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Glam Rhinestone Chrome Sandals

    You'll absolutely adore the casual glam style of these rhinestone chrome sandals! They feature a square-shaped toe, a triple strap design with mini rhinestone embellishments, an open back for easy on-and-off styling, and a metallic flat sole for comfortable wear. Pair with rhinestone stud earrings.

    Fit & Features

    • Square-shaped toe
    • Triple strap design
    • Mini rhinestones
    • Slip-on-and-off styling
    • Metallic flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1092

    Category Name: Vacation Looks

    Price: $12.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Mood High-Rise Denim Mom Shorts

    These cute and casual denim mom shorts will have you in the mood for fun weekend plans! They feature a high-rise waist, front button closures, and a frayed, raw-cut hem. The medium-wash denim fabric has a rigid fit with no stretch. Style with a graphic tee and sandals.

    Fit & Features

    • High-rise waist
    • Front button closures
    • Five belt loops
    • Two front and back pockets
    • Frayed, raw-cut hem
    • Medium-wash denim fabric, rigid fit, no stretch
    • Runs true to size

    Style Number/Barcode: 06603-0350

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Playful In Denim Lace-Up Romper

    Play up your style in this fun and flirty denim romper perfect for visiting a beach town or a casual hang with friends! It features a sleeveless square neck, spaghetti straps that create the lace-up open-back design, back pockets, and a fitted short-length hem. Complete the look in cute flat sandals.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Lace-up open-back design
    • Back pockets, zipper and hook-eye closure
    • Fitted short-length hem
    • Medium wash denim, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06603-0321

    Category Name: Vacation Looks

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fierce And Flirty Leopard Floral Maxi Skirt

    Show up fierce and flirty in this leopard floral maxi skirt! The flattering high waist accentuates your curves while the daring side slit adds movement and drama to every step. Pair with the matching tie-front top.

    Shop Matching Top: Fierce And Flirty Leopard Floral Tie-Front Top

    Fit & Features

    • Leopard floral print, mesh fabric, stretchy knit lining
    • High-rise waist
    • High side slit
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000054

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Summer Style Cutout Denim Romper

    Show off a sultry summer style with this alluring denim romper! It features a sleeveless V-neckline, a center bust cutout with a tie-front design, a bold waist cutout, adjustable spaghetti straps, fitted shorts with a high waist silhouette, and a form-hugging fit. Complete the look with sleek hoop earrings and strappy mules.

    Fit & Features

    • Sleeveless V-neckline, center bust cutout, tie-front detail
    • Waist cutout, back zipper and hook-eye closure
    • Adjustable spaghetti straps, back zipper closure
    • Fitted shorts, high waist silhouette
    • Form-hugging fit
    • Denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06603-0248

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Coveted Cool Girl Square Gold Trim Sunglasses

    Covet that cool girl style in these sleek square sunglasses featuring a plastic frame with gold trim sides, quilted-pattern arms, and tinted lenses. Complete the look in a faux leather blazer.

    Fit & Features

    • Square plastic frame
    • Gold trim sides
    • Quilted-pattern arms
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-0996

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Life's A Highway Aviator Sunglasses

    Can't you imagine wearing these sleek aviator sunglasses on your next road trip or driving down by the beach? They feature a rose gold metal frame, rubber nose supports, a classic aviator design, and mirrored lenses. Complete the look in a graphic crop top and denim shorts!

    Fit & Features

    • Classic aviator design
    • Sleek rose gold metal frame
    • Rubber nose supports
    • Mirrored lenses

    Style Number/Barcode: 07008-1003

    Category Name: Vacation Looks

    Price: $4.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stay Shady Woven Visor

    Shade your eyes and look cute doing it with this woven visor featuring a classic wide brim and a velcro back closure. Complete the look in a basic tee and skort for exploring a beach city!

    Fit & Features

    • Classic wide brim
    • Velcro back closure
    • Woven material

    Style Number/Barcode: 07302-1386

    Category Name: Vacation Looks

    Price: $1.97 $5.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacay Muse Tropical Print Halter Top

    You'll be an alluring vacay muse in this tropical print halter top! It features a sleeveless sweetheart neckline, thin halter straps, and an ultra-cropped, fitted hem. Style with the matching maxi skirt for a dreamy look.

    Shop Matching Bottoms: Vacay Muse Tropical Print Maxi Skirt

    Fit & Features

    • Sleeveless sweetheart neckline
    • Thin halter straps
    • Ultra-cropped, fitted hem
    • Tropical print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4689

    Category Name: Vacation Looks

    Price: $4.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Muse Tropical Print Maxi Skirt

    You'll be an alluring vacay muse in this tropical print maxi skirt! It features a high-rise waist, ruching down the side, a maxi-length asymmetric hem creating a thigh-high side slit, and a curve-hugging fit. Style with the matching crop top for a dreamy look.

    Shop Matching Top: Vacay Muse Tropical Print Halter Top

    Fit & Features

    • High-rise waist
    • Side ruching
    • Maxi-length asymmetric hem, high-side slit
    • Form-hugging fit
    • Tropical print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0785

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Throw It Back Low-Rise Micro Mini Skirt

    Throw it back to the early 2000s with this trendy micro mini skirt! It features a low-rise waist, large front pockets, back pockets, and an ultra-mini-length hem with a frayed edge and the pocket lining peaking below. Style this form-hugging mini skirt with a crop top, sandals, and a cool pair of shades.

    Fit & Features

    • Low-rise waist, five belt loop accents
    • Front button, hidden zipper closure
    • Large front pockets, back flap pockets, button closures
    • Micro mini-length hem, frayed edge, pocket lining
    • Form-hugging fit
    • Twill fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06301-0147

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Western Flair Faux Suede Crop Top

    Show off a western flair in this trendy faux suede crop top! Featuring a sleeveless halter neckline with tie-back spaghetti straps, an open back, and a pointed, cropped hem with thin waist straps, this cute top is a summertime staple! Style with printed flare pants and strappy sandals.

    Fit & Features

    • Sleeveless halter neckline
    • Tie-back spaghetti straps
    • Open back
    • Pointed, cropped hem
    • Thin waist straps, tie closure
    • Faux suede fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4192

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glitzy Bejeweled Thong Sandals

    Keep it glitzy with these glamorous bejeweled sandals! They feature a round toe, a metallic thong strap design with clear PVC strap detailing, chain accents, stunning gemstone embellishments, and an open back for easy on-and-off styling. Pair with hoop earrings.

    Fit & Features

    • Round toe
    • Metallic thong strap design
    • Clear PVC straps, chain accents
    • Gemstone embellishments
    • Open back, slip-on-and-off styling
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1133

    Category Name: Vacation Looks

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Festive Babe Crochet Fringe Top

    Get ready for festival season babe! This boho crochet fringe top features a sleeveless halter neck with a tie closure, an open back, and a cropped length with cascading fringe down the front. Complete the look in distressed denim shorts and a ring set.

    Fit & Features

    • Sleeveless halter neck with tie closure
    • Open back
    • Cropped length
    • Crochet design with front fringe
    • Sweater knit fabric
    • No stretch
    • Runs true to size

    Style Number/Barcode: 06005-1690

    Category Name: Vacation Looks

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dance All Day Crochet Halter Top

    Get ready to dance at every festival looking so fire in this crochet halter top featuring a trendy open-back with tie closure and a V-neck atop an ultra-cropped hem. Complete the look in boho flare pants.

    Fit & Features

    • Sleeveless, halter V-neck, tie closure
    • Open-back
    • Crochet design, unlined sweater knit fabric
    • No stretch
    • Runs true to size

    Style Number/Barcode: 06005-1694

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cherish Me Eyelet Lace Skater Dress

    All eyes on you in this lovely eyelet lace skater dress as the bride-to-be or graduate! The dress features a sleeveless sweetheart neck with flirty ruffle trim, adjustable spaghetti straps, a front bust tie and button accents, and a tiered fit and flare silhouette with a ruffled short hem. Complete the look in platform sandals.

    Fit & Features

    • Sleeveless sweetheart neck with ruffle trim
    • Adjustable spaghetti straps
    • Front bust tie, button accents
    • Tiered, skater silhouette
    • Ruffled short-length hem
    • Eyelet lace cotton fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4907

    Category Name: Vacation Looks

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hint Of Radiance Rhinestone Flat Sandals

    Treat your feet to a hint of radiance with these flat sandals - perfect for brides, graduates, or dressy parties! They feature a square toe, a twisted toe strap with rhinestone embellishments, and an ankle strap with buckle closure on faux leather material. Complete the look with a glam ring set.

    Fit & Features

    • Square toe
    • Twisted toe strap with rhinestones
    • Ankle strap with buckle closure
    • Flat sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1091

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale