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.

  • A Classic Chic Choice Trouser Shorts

    These dressy woven trouser shorts are a classic chic choice for drinks with the girls! They feature a high-rise waist, belt loops, side pockets, pleated detailing, and a fitted silhouette. The woven fabric has a lightweight feel for comfortable wear. Style with a cropped blouse and strappy mules.

    Fit & Features

    • High-rise waist, belt loops
    • Hidden front zipper, button, and hook and bar closures
    • Side pockets
    • Pleating
    • Fitted silhouette
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0260

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Like Summer Crochet Maxi Skirt

    Sweet like summer, this crochet maxi skirt was made to flirt. With a high-rise waist, scalloped trim, and high-cut side slit, it's your new go-to for coastal vibes. Style with the matching bralette top.

    Shop Matching Top: Sweet Like Summer Crochet Bralette Top

    Fit & Features

    • Sheer crochet knit fabric, moderate stretch
    • High-rise waist, scalloped trim
    • Adjustable tie-front drawstring
    • Thigh-high side slit
    • Maxi-length fitted silhouette, scalloped hem
    • Runs true to size

    Style Number/Barcode: 06501-000031

    Category Name: Vacation Looks

    Price: $45.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: L

    Product Badge:
    • Part of a Set
  • Chic Encore Crepe Slit Maxi Dress

    Prepare for a standing ovation whenever you're seen in this crepe maxi dress perfect for casual wine nights by the fire pit or a spring getaway! Featuring a sleeveless square neck, spaghetti straps, a curve-hugging silhouette, and a sultry high slit along the flowy long hem. Complete the look in cute flat sandals.

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Curve-hugging silhouette
    • Front high slit
    • Flowy maxi-length hem
    • Crepe knit fabric, mini-length knit lining
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5058

    Category Name: Vacation Looks

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachside Babe O-Ring Triangle Bikini Top

    Capture a babe look in this bikini top sitting beachside! The swimsuit top boasts classic triangle cups with a chic O-ring insert and dual adjustable back ties so you can customize the fit. Pair with the matching bikini bottoms.

    Shop Matching Bikini Bottoms: Beachside Babe High-Rise Bikini Bottoms

    Fit & Features

    • Textured fabric
    • Triangle cups, O-ring insert
    • Removable padded bra cups
    • Dual adjustable back ties
    • Runs true to size

    Style Number/Barcode: 07104-0715

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Fantasy Crepe Peplum Tube Top

    You're always in for a sweet time in this crepe tube top designed with a flirty peplum silhouette and crop hem perfect for pairing with shorts.

    Fit & Features

    • Crepe woven fabric
    • Strapless neckline
    • Ruched bust, stretchy smocked waist
    • Peplum crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000033

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Boost Your Glow Sequin Corset Top

    Boost your glow in this shimmering sequin corset top featuring a sleeveless, square neck, tank-style straps, flexible boning, a fitted crop hem, and back hook-eye closures. Complete the look in a chic mini skirt and boots for a sparkly night out.

    Fit & Features

    • Sleeveless, square neck, tank-style straps
    • Flexible boning
    • Fitted crop hem
    • Back hook-eye closures
    • Sequin-knit, lined, minimal stretch
    • Fits true to size

    Style Number/Barcode: 06003-1948

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunset Beauty Off-The-Shoulder Marble Chiffon Crop Top

    Radiate your beauty in this mesmerizing marble chiffon crop top on sunset beach walks! The breezy chiffon fabric is detailed with a pretty marble print for a dreamy vibe. The top features an off-the-shoulder neckline, long flowy bishop sleeves with cinched hems, a cropped cinched hem, and a relaxed fit for an effortless look. Style with denim shorts and sandals.

    Fit & Features

    • Marble-printed chiffon fabric, sewn-in knit lining
    • Off-the-shoulder neckline
    • Long bishop sleeves with cinched hems
    • Cropped cinched hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06003-2579

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Soiree Hour Lace-Up Ruffled Floral Midi Dress

    When the cocktails are poured and the music starts playing it's time to unveil this floral chiffon midi dress! Perfect for daytime soirees or showers, this midi dress features a flattering scoop neckline adorned with adjustable spaghetti straps. The lace-up back and flowy ruffled silhouette offer a touch of trendiness to this midi-length dress! Complete the look with earrings and wedges.

    Fit & Features

    • Floral print, chiffon fabric lined with woven fabric
    • Scoop neckline
    • Adjustable spaghetti straps
    • Lace-up back, zipper and hook-eye closure
    • Flowy ruffled silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3411

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Necessity Nylon Sling Fanny Pack

    For all the concert cuties or sporty babes out there, this nylon sling fanny pack is a cute necessity to hold your essentials in style! This trendy fanny pack offers a detachable and adjustable long strap for multiple styling options, a back zipper pocket for extra storage, and a top zipper that reveals a spacious interior with four mesh pockets perfect for cards, keys, and cash. Complete the look in platform sneakers.

    Fit & Features

    • Detachable and adjustable long strap
    • Back zipper pocket
    • Top zipper
    • Spacious interior with four mesh pockets
    • Nylon woven material

    Style Number/Barcode: 07203-1993

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mexico Tulum Graphic Tee

    Grab your crew and head on vacay with this cute knit graphic tee with a paradise graphic and a script that reads "Mexico Tulum".

    Fit & Features

    • Stretchy cotton-blend knit fabric
    • Short sleeves
    • Crew neckline
    • Paradise graphic, script reads "Mexico Tulum"
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000037

    Category Name: Vacation Looks

    Price: $22.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Drama Meets Paradise Floral Maxi Dress

    Giving goddess energy with every step you take. This mesh maxi dress clings in all the right places with a daring cowl neckline and a strappy open back made to be seen.

    Fit & Features

    • Floral print, mesh fabric, soft stretchy knit lining
    • Plunging cowl neckline
    • Strappy open back with hoop insert
    • Form-hugging fit
    • Flowy maxi hem and front slit
    • Runs true to size

    Style Number/Barcode: 05101-000352

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Sway With Me Halter V-Neck Paisley Skater Dress

    This breezy skater dress brings the romance with a halter neckline and swingy silhouette made to float with you. Perfect for golden hour snaps, weekend wandering, or spontaneous getaways!

    Fit & Features

    • Paisley print, woven fabric, bust lining
    • Halter V-neckline with spaghetti strap ties
    • Stretchy smocked bust
    • Tie back design
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5575

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: NAVY, OLIVE, RUST

    Available Size: XS, S, M, L

  • Romance For Two High Rise Slit Maxi Skirt

    You'll be sure to fall in love with this flowy maxi skirt for a dreamy summer wardrobe! With its elasticized high-rise waist, flowy tiered silhouette, and front slit, you'll feel effortlessly elegant. Complete the look with the matching top.

    Shop Matching Top: Romance For Two Sleeveless Crop Top

    Fit & Features

    • Gauze woven fabric, short woven lining
    • High-rise elasticized waist
    • Front slit
    • Flowy tiered silhouette
    • Runs true to size

    Style Number/Barcode: 06301-0189

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Harper Mid-Rise Skinny Jeans By Windsor Denim

    The jeans you never knew you needed! The Harper mid-rise jeans by Windsor denim will fit your body like a glove. She features a flattering skinny-leg design, and ankle-length hem, and is composed of clean dark wash denim with vintage-inspired color fading. Style with an edgy corset top for dinner and drinks!

    Fit & Features

    • Mid-rise waist
    • Skinny-leg design
    • Ankle-length hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Clean dark wash denim, color fading, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06602-0382

    Category Name: Vacation Looks

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylish Appearance Side-Tie Wrap Denim Skort

    Your summer style wouldn't be the same without this mini denim skort to make stylish appearances! This form-hugging, high-waisted denim skort boasts a stylish faux wrap skirt overlay with a side tie, adding both function and flair to your wardrobe. The frayed hem adds a touch of edginess. Complete the look in a basic top.

    Fit & Features

    • Dark wash denim, slight stretch
    • High-rise waist, front zipper closure
    • Faux wrap skirt overlay, side-tie
    • Form-hugging fit
    • Frayed short hem
    • Runs true to size

    Style Number/Barcode: 06603-0390

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: DARK, DENIM

    Available Size: S, M, L

  • Classic Chic Mock Neck Sweater Dress

    This classic chic sweater dress is perfect for styling up or down this winter season. It features an on-trend mock neckline, long fitted sleeves, a short, curve-hugging silhouette, and a front slit accent. The knit fabric offers plenty of stretch. Pair with knee-high boots and sleek hoops.

    Fit & Features

    • Ribbed mock neckline
    • Long fitted sleeves
    • Mini-length hem, front slit
    • Curve-hugging silhouette
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1616

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Resort-Ready Tropical Print Mesh Duster

    You'll be resort-ready when you pack this tropical print mesh duster in your carry-on! It features long fitted sleeves, an open front, a long-length hem with a flowy silhouette, and a multi-colored tropical print pattern on the airy sheer mesh fabric. Style over a mini dress with clear heels!

    Fit & Features

    • Long fitted sleeves
    • Open front
    • Long-length hem
    • Flowy silhouette
    • Multi-colored tropical print
    • Sheer mesh fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06202-0436

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Effortless Square Neck Rib Knit Bodysuit

    All you need is this sleeveless basic bodysuit and your fave denim to create a simply effortless and cute look! Crafted from stretchy rib knit fabric that fits like a glove, this bodysuit boasts a square neckline, tank shoulder straps, and a thong bottom with snap-button closures for convenience. Style with high-rise denim jeans and sandals.

    Fit & Features

    • Stretchy rib knit fabric
    • Square neckline
    • Tank shoulder straps
    • Thong bottom, snap-button closures
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 07109-0367

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Back Of My Mind Crepe Slip Dress

    You'll be unforgettable once they see you in this crepe slip dress perfect for casual parties and celebrations! It features a sleeveless V-neck, spaghetti straps, a form-hugging silhouette, and a sultry front slit along the midi-length hem. Style with simple hoop earrings to complete the look!

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Form-hugging silhouette
    • Front slit accent
    • Midi-length hem
    • Crepe fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4826

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fave Trend Oversized Cat-Eye Sunglasses

    These fab oversized cat-eye sunglasses will be your new fave trend to style up! They feature a cat-eye rimless design, a thin metal nose bridge, thin metal arms with a front cutout, rubber nose pads for support, and gradient-tinted lenses with stud accents. Pair with hoop earrings and a mini handbag for an everyday 'fit.

    Fit & Features

    • Oversized cat-eye rimless design
    • Thin metal nose bridge and arms, cutout details
    • Rubber nose pads
    • Gradient-tinted lenses, stud details
    • 100% UV protection

    Style Number/Barcode: 07008-1073

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Good At Being Bad Lace Hot Shorts

    Earn style cred in these lace hot shorts with frilly ruffles and a cheeky fit. Pair with the matching top.

    Fit & Features

    • Lace fabric
    • Low-rise waist
    • Frilly ruffled design
    • Cheeky fit
    • Runs true to size

     

    Shop The Matching Top: Good At Being Bag Lace Crop Top

    Style Number/Barcode: 06503-000027

    Category Name: Vacation Looks

    Price: $28.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Sweet Harmony Chiffon Midi Dress

    Your sweet style personality goes in harmony with this chiffon midi dress perfect for any upcoming weddings and parties! The knee-length dress features short puff sleeves, a sweetheart neckline, princess seams, and a front flirty slit along the A-line silhouette. Pair with a chic ring set and heels.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neck
    • Princess seams, front slit, back zipper and hook-eye closure
    • A-line silhouette
    • Midi-length hem
    • Airy chiffon fabric, knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1850

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance For Two Sleeveless Crop Top

    You'll be sure to fall in love with this crop top for a dreamy summer wardrobe! With its square neckline, adjustable spaghetti straps, and crop hem, you'll feel effortlessly elegant. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Romance For Two High Rise Slit Maxi Skirt

    Fit & Features

    • Gauze woven fabric, partially woven lining
    • Adjustable spaghetti straps
    • Square neckline
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2420

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendsetting Frames Square Sunglasses

    These square sunglasses are perfect for creating trendy looks while driving or in any sunny place!

    Fit & Features

    • Colored square frames
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000017

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: GREEN

    Available Size: NS