Vacation outfits should feel as effortless as your out-of-office vibe. Think long floral dresses that move with the breeze, easy cover-ups for poolside lounging, and bold two-piece sets that pop in every photo. From beachy maxis that bring instant elegance to denim shorts that nail casual cool, each piece blends comfort with style so you never have to choose between the two. These looks are made for packing light, looking chic, and serving up Instagram-worthy vacation moments.

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STYLE SPOTLIGHT

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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.

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
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
Dainty Leaf Fringe Hoop Earrings
These dainty detailed hoops will bring that boho-chic glam! They feature a textured hoop with leaf-shaped charms in a dangling fringe design. Style with a layered necklace set.

Fit & Features
- Textured hoop
- Leaf-shaped charms, fringe design
- Rubber stopper
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1560

Category Name: Vacation Looks

Price: $2.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Always Impressed Satin Pleated Maxi Skirt
You'll always be dressed to impress in this satin pleated maxi skirt featuring an elasticized high-rise waist, slim bodycon silhouette, and a center front side ruched seam atop a flirty slit. Style with the matching top for a night of dinner and dancing!

Shop Matching Top: Always Impressed Satin Pleated Crop Top

Fit & Features
- High-rise elasticized waist
- Slim, bodycon silhouette
- Center front side ruched seam, high slit
- Maxi-length hem
- Satin pleated fabric, backside lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06501-0793

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Always Impressed Satin Pleated Crop Top
You'll always be dressed to impress in this satin pleated top featuring a sleeveless V-neck, wide straps, a center-ruched bust seam, and a fitted crop hem. Style with the matching skirt for a night of dinner and dancing!

Shop Matching Bottoms: Always Impressed Satin Pleated Maxi Skirt

Fit & Features
- Sleeveless V-neck
- Wide straps
- Center-ruched bust seam
- Fitted crop hem
- Satin pleated fabric, bust lining
- Minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4716

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Mixing It Up Twist Sweater Top
Mix up your everyday style in this flirty sweater crop top featuring a sleeveless, sweetheart neck, tank-style straps, and a twisted bodice on stretchy and soft rib-knit fabric. Complete the look in high-rise skinny jeans for a brunch.

Fit & Features
- Sleeveless, sweetheart neck, tank-style straps
- Twisted bodice
- Cropped hem
- Soft and stretchy
- Sweater rib-knit fabric
- Fits true to size
Style Number/Barcode: 06005-1310

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Totally In Fringe Rhinestone Denim Shorts
You can be found in these denim shorts all season long! They feature a flattering high-rise waist, cascading rhinestone fringe along the front, and a cut-off style hem on premium non-stretch denim fabric. Complete the look in a flirty crop top and cowboy boots for a festival!

Fit & Features
- High-rise waist
- Cascading front rhinestone fringe
- Cut-off style hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Premium non-stretch denim fabric
- Runs true to size
Style Number/Barcode: 06603-0346

Category Name: Vacation Looks

Price: $6.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
On The Verge Chiffon A-Line Midi Dress
You'll be on the verge of a stylish breakthrough with the addition of this chiffon midi dress to your fashion closet! Effortless and breezy, this dress features a sleeveless v-neckline, halter spaghetti straps, a lace-up open back that lets you customize the fit, and an asymmetrical hem with a flirty slit. Complete the look with stiletto heels and a bracelet!

Fit & Features
- Sleeveless v-neckline
- Halter spaghetti straps
- Lace-up open back
- A-line silhouette
- Asymmetrical midi-length hem, slit accent
- Chiffon fabric, stretchy knit lining
- Fits true to size
Style Number/Barcode: 05102-4905

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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Vacation Looks

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STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials