Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • Don't Tempt Me Textured Slit Crop Top

    Don't let your girls tempt you from taking this sultry crop top out for a good time! It features fitted long sleeves, an open V-neckline, a center front slit accent, and is composed of a textured sheer knit fabric. Complete the look in distressed denim jeans.

    Fit & Fetaures

    • Fitted long sleeves
    • Open V-neckline
    • Center front slit accent
    • Cropped hem
    • Textured sheer knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-5267

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Allure One-Shoulder Cutout Waist Knit Midi Dress

    Bring the bold allure to your summer 'fits with this sultry cutout waist midi dress! Made with a lined stretchy ribbed knit fabric, the mid-length dress features a sleeveless one-shoulder neckline and a tank strap with a trendy twisted-back design. The asymmetric goes around the waist, accented with a chic O-ring cutout at the front. The midi-length hem is detailed with a high-cut side slit along the figure-flaunting bodycon silhouette. Style with lace-up sandals for a weekend getaway!

    Fit & Features

    • Stretchy ribbed knit fabric, knit lining
    • One-shoulder neckline, tank strap with twisted-back design
    • Asymmetric waist cutout
    • Front O-ring cutout
    • High side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5697

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine Livin' High Rise Palazzo Crochet Pants

    These crochet palazzo pants were meant for living under the sun! Whether you're heading to a festival or a getaway, these pants will keep you boho-cute. They feature an elasticized high-rise waist and a flattering relaxed silhouette. Complete the look with the matching top.

    Shop Matching Top: Sunshine Livin' Halter Crochet Crop Top

    Fit & Features

    • Crochet fabric lined with stretchy knit
    • High-rise elasticized waist
    • Relaxed silhouette
    • Runs true to size

    Style Number/Barcode: 06302-0823

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Paradise Bound Tropical Floral Satin Midi Dress

    You'll be ready to jet set off to paradise in this gorgeous tropical floral satin midi dress! The silky sleek satin woven fabric is accented with a blooming tropical floral print, an iconic look for your vacay getaway. The mid-length dress features a sleeveless V-neckline, adjustable spaghetti straps with a racer-back design, a flattering tie-back detail, and an asymmetric hanky hem with a flowy A-line silhouette for that effortless vibe. Style with hoop earrings and a layered necklace.

    Fit & Features

    • Tropical floral print
    • Non-stretch satin woven fabric with top knit lining
    • V-neckline
    • Adjustable spaghetti straps, racer-back design
    • Tie-back design
    • Asymmetric hanky hem, A-line fit
    • Runs true to size

    Style Number/Barcode: 05101-3468

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off The Vine Lace Trim Rose Print Bustier

    Stop and smell this romantic rose print bustier to dress up your favorite bottoms. The delicate lace trim neckline and straps create a stunning silhouette, while the fitted crop hem gives you a flattering look.

    Fit & Features

    • Rose print, eyelet woven fabric, sewn-in woven lining
    • Lace trim sweetheart neckline
    • Lace trim adjustable shoulder straps
    • Hidden front hook and eye closures
    • Stretchy smocked back panel
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000014

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

  • Simply Chic Side Slit Skort

    Create a simply chic everyday outfit with this classic crepe skort. It features a high-rise waist, a back zipper closure, a mini-length overlay with a side slit, and fitted shorts. The crepe fabric offers a moderate stretch. Complete the look with a bodysuit and mules.

    Fit & Features

    • High-rise waist
    • Back zipper closure
    • Mini-length overlay, side slit
    • Fitted shorts
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06503-1038

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bloom Baby Floral Halter Cutout Mini Dress

    Soft, flirty, and ready for golden hour—this halter mini dress is a little bit sweet, a little bit daring. Flowy ruffles and a smocked waist keep the vibe effortlessly pretty for sunset dinners or dressy events!

    Fit & Features

    • Floral print, chiffon woven fabric, woven lining
    • Sweetheart twist halter neckline, tie straps
    • Cutout bust accent
    • Stretchy, smocked, fitted bodice
    • Drop waist seam
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000243

    Category Name: Vacation Looks

    Price: $59.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Flirty In Fall Cable Knit Dress

    Stay flirty and cozy this fall in this cable knit midi dress! It features long sleeves, a mock neck, a bodycon silhouette, and a sultry open-back design. Perfect for styling with faux suede booties for your weekend plans!

    Fit & Features

    • Long sleeves
    • Mock neck
    • Bodycon silhouette
    • Open-back design
    • Midi-length hem
    • Soft cable knit sweater fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1614

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Paradise Awaits Cutout Tropical Knit Jumpsuit

    This sexy cutout tropical knit jumpsuit is a definite must when packing for your trip to paradise! The stretchy lightweight knit fabric showcases an eye-catching palm leaf print perfect for your dream vacay. It features a sleeveless plunging neckline with cross-front spaghetti straps and a halter tie-back design for a customized fit. The alluring waist cutouts lead to an open lower back for added sultry flair. The hip-hugging fit flows down to a relaxed wide-leg silhouette. Complete the look with strappy sandals.

    Fit & Features

    • Tropical printed knit fabric, lined bust, plenty of stretch
    • Plunging neckline with cross-front spaghetti straps, halter tie-back design
    • Waist cutouts, open back
    • Hip-hugging fit
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2494

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On A Vacay Strapless Tropical Slit Maxi Dress

    From sunny vacations to island getaways, this tropical maxi dress is destined to go with you on your next trip! 

    Fit & Features

    • Tropical palm print, mesh fabric lined with stretchy knit
    • Strapless neckline
    • Form-hugging silhouette
    • High side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6110

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Style Knit Right Chenille Sweater

    You'll love styling this chenille crop sweater into your weekly outfit rotation! It features cozy long sleeves, a crew neck, and a striped color block pattern composed of a cable knit design. The ultra-soft chenille fabric has no stretch. Complete the look in boyfriend jeans for a cute and casual vibe!

    Fit & Features

    • Long sleeves
    • Crew neck
    • Striped color block pattern
    • Cropped hem
    • Cable knit design
    • Chenille fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06005-1562

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Forever Fabulous Cat-Eye Sunglasses

    These sleek cat-eye sunglasses will be forever fab and always on-trend! They feature a chic oversized cat-eye design crafted with a plastic frame and arms, built-in nose pads for support, and tinted lenses. Style these shades with hoop earrings.

    Fit & Features

    • Oversized cat-eye design
    • Plastic frame and arms
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1070

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: NS

  • City Streets Slouch Stiletto Boots

    Walk down the city streets like it's your runway in these chic slouch stiletto boots! They feature an above-the-ankle height with a trendy slouched design, a pointed toe, and a sleek stiletto heel. Style with a crossbody bag.

    Fit & Features

    • Above-the-ankle height
    • Slouchy silhouette
    • Partial inner zipper closure
    • Pointed toe
    • Stiletto heel
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1592

    Category Name: Vacation Looks

    Price: $8.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Updated Chic High Rise Slit Linen Maxi Skirt

    Whether you're heading on vacation or out on the weekend, this linen maxi skirt will help you look chic all season! The high-rise waist and form-hugging fit flatter your figure while the adjustable front drawstring allows for a perfect fit. The high slit adds a touch of drama and the maxi-length hem exudes effortless style. Complete the look in a corset top and wedges.

    Fit & Features

    • Linen blend fabric, woven lining, no stretch
    • High-rise waist, side zipper and hook-eye closure
    • Adjustable front drawstring
    • High slit
    • Maxi-length, form-hugging
    • Runs true to size

    Style Number/Barcode: 06301-0188

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Crush Striped Crochet Bralette Top

    POV: you just found your new fave beach-to-brunch vibe. This striped crochet bralette top serves laid-back heat with an open back and tie details made for turning heads from sunrise to sunset.

    Shop Matching Bottoms: Summer Crush Striped Crochet Midi Skirt

    Fit & Features

    • Crochet knit fabric
    • Striped pattern
    • Sleeveless triangle bust design
    • Thin shoulder straps
    • Open back, tie-back design
    • Fitted ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-000034

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Mixed Signals 50/50 Knee-High Boots

    Don't get your signals crossed, these knee-high boots are just what your closet needs! They feature an almond toe, low-block heel, side zipper, and are half faux suede and knit compression. Style with a chic handbag. 

    Fit & Features

    • Almond toe
    • Low-block heel
    • Side zipper
    • Knee-high length
    • Half faux suede, half knit compression
    • Runs true to size

    Style Number/Barcode: 07402-0696

    Category Name: Vacation Looks

    Price: $8.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Play My Song Lace Fringe Crop Top

    Move to the music in this lace fringe crop top at festivals, concerts, or your fave country bar!

    Fit & Features

    • Lace fabric, bust knit lining
    • Strapless neckline
    • Sheer fitted crop hem, fringe trim
    • Runs true to size

    Style Number/Barcode: 06001-000105

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Energy Over The Knee Boots

    Embody a sleek fashion sense in these over-the-knee boots perfect for elevating your fit! They feature an almond toe, block heel, inner side zipper closure, and an adjustable drawcord. Complete the look in a trendy sweater dress.

    Fit & Feature

    • Almond toe
    • Block heel
    • inner side zipper closure
    • Over-the-knee length shaft
    • Adjustable drawcord
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0833

    Category Name: Vacation Looks

    Price: $4.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Call The Shots High-Rise Wide-Leg Pants

    Decide your fashion direction in these high-rise pants for creating unique and stylish outfits! They feature a flattering high-rise waist and a breezy wide-leg silhouette for comfort and chicness. Style with a crop top, earrings, and wedges!

    Fit & Features

    • Woven fabric with minimal stretch
    • High-rise waist, back elastic band
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06402-1395

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutie At Heart Cutout Mini Skirt

    Sweeten your every vibe in this bodycon mini skirt with a heart insert and a cutout that adds a cute look!

    Fit & Features

    • Smooth knit stretchy fabric
    • High-rise waist
    • Heart insert and cutout
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000006

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Let It Flow Crochet V-Neck Skater Dress

    Flowy and flirty! Twirl all day in this crochet V-neck skater dress featuring a sleeveless bodice with adjustable spaghetti straps, an open back with tie closure, and a tiered short hem. Composed of a gauze woven fabric with an inner lining. Finish the look in trendy mules.

    Fit & Features

    • Sleeveless bodice, crochet V-necklined
    • Adjustable spaghetti straps
    • Open-back, tie closure
    • Tiered short hem
    • Skater silhouette
    • Airy gauze woven fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4397

    Category Name: Vacation Looks

    Price: $21.97 $47.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Mode Cotton Bra Top

    Activate summer mode with this lightweight cotton bra top featuring a sleeveless V-neckline, adjustable spaghetti straps, and a fitted ultra-cropped hem. Style with the matching button-down top and high-rise shorts for an effortlessly chic look.

    Shop Matching Set: Summer Mode Button-Down Cotton Top, Summer Mode High-Rise Cotton Shorts

    Fit & Features

    • Textured cotton fabric
    • Sleeveless V-neckline, surplice design
    • Adjustable spaghetti straps
    • Stretchy smocked back
    • Fitted ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-000082

    Category Name: Vacation Looks

    Price: $22.90

    Availability: In Stock

    Available Color: CHARTREUSE

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • High Waist Linen Shorts

    Fall back on basic shorts with a stylish twist! These shorts are ready for warmer days with a high-rise waist, a tie-waist belt, a wide leg hem, and a back zipper closure for a secure fit. Complete look with a floral bodysuit and wedges for the perfect brunch outfit with the squad!

    Fit & Features

    • High-rise waist
    • Tie-waist belt
    • Wide leg hem
    • Back zipper closure
    • Lined linen fabric 
    • Relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06303-0150

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Day Dream Tie-Front Crop Top

    Look like a tropical day dream in this crop top while on vacation! The flowy long sleeves with banded cuffs ensure a comfortable fit, while the tie-front closure and vibrant tropical print add a touch of paradise to your outfit. Complete the look with the matching pants and skirt.

    Shop Matching Pants: Tropical Day Dream High-Rise Wide Leg Pants
    Shop Matching Skirt: Tropical Day Dream High-Rise Wrap Mini Skirt

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Flowy long sleeves, banded cuffs
    • Tie-front closure
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06202-0451

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale