Vacation Looks

Loading...

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.

  • Put A Ring On It Sweater Midi Dress

    A sultry take on a classic staple! This sweater midi dress features fitted long sleeves, a v-neckline, a front cutout with a ring hoop insert, and a form-hugging silhouette with a flirty front slit. Style with pointed-toe booties to complete the look!

    Fit & Features

    • Fitted long sleeves
    • V-neckline
    • Front cutout with a ring hoop insert
    • Form-hugging silhouette
    • Front slit, midi-length hem
    • Rib-knit sweater fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1612

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Henley Formal Lace-Up Midi Dress

    Special Occasion

    Lace-up in a formal dress that brings the radiance to your evening! Henley features a sleeveless square neckline, spaghetti straps, a bold lace-up back, and a midi-length silhouette accented with a high-side slit. The dress is composed of a lined crepe fabric that offers a form-flattering fit with a moderate stretch. Complete look with rhinestone heels and a sphere clutch

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Lace-up back 
    • Midi length silhouette
    • High side slit
    • Lined crepe fabric 
    • Form-hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05001-0755

    Category Name: Vacation Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Set It Off Ruffled Bodycon Dress

    Set off your night with a head-turning bodycon that raises the heat! The dress features a sleeveless wrap V-neckline, spaghetti straps, a ruched body, and a mini-length silhouette with a ruffled hem. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with rhinestone heels and a clutch. 

    Fit & Features

    • Sleeveless wrap V-neckline
    • Spaghetti straps
    • Ruched body
    • Mini length silhouette, ruffled hem 
    • Smooth knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4464

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Breeze Linen High Slit Maxi Skirt

    Channel that coastal chic vibe with this breezy linen maxi skirt featuring a tiered design, high-cut side slit, and flowy A-line silhouette.

    Fit & Features

    • Linen-blend fabric
    • High-rise waist
    • Tiered design
    • Thigh-high side slit
    • Flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 06301-000004

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keep It Light Sleeveless Linen Corset Top

    Keep it light and effortless in this linen corset top for a day spent under the sun! With a sleeveless V-wired neckline and tank straps, this top offers a flattering fit. The cropped hem flaunt your figure, while the linen fabric elevates the look. Style with the matching bottoms.

    Shop Matching Bottoms: Keep It Light High Rise Linen Palazzo Pants

    Fit & Features

    • Linen woven fabric, no stretch
    • Tank straps
    • Cropped hem
    • Multiple back hook and eye fasteners
    • Runs true to size

    Style Number/Barcode: 06003-2359

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Card Knit Cutout Crop Top

    Match your wardrobe to your mood! This flirty crop top features long sleeves, a v-neck, and dual front twist accents and cutouts on brushed knit fabric with plenty of stretch. Style with high-rise jeans for happy hour!

    Fit & Features

    • Long sleeves
    • V-neck
    • Dual front twist accents and cutouts
    • Cropped hem
    • Brushed knit fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06001-4554

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Classic Button-Front Henley Bodysuit

    This casual classic henley bodysuit will be a new wardrobe staple! It features a V-neckline, a partial faux button-front design, short sleeves, a thong bottom with a dual snap-button closure, and a form-hugging fit. The ribbed knit fabric offers plenty of stretch. Style with high-rise denim and your fave mules.

    Fit & Features

    • V-neckline
    • Partial faux button-front design
    • Short sleeves
    • Thong bottom, dual snap-button closure
    • Form-hugging fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06002-1560

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • A Sweet Look Sleeveless Ruffled Skater Dress

    A sweet skater dress for showers or brunch! With its romantic sweetheart neckline and bust tie, you'll feel so flirty. The adjustable spaghetti straps allow for a perfect fit while the ruffled skater silhouette and short-length hem add a touch of playful charm. The partially smocked back offers added stretch. Complete the look with a heart necklace and sandals.

    Fit & Features

    • Gauze woven fabric with stretchy knit lining
    • Sweetheart neckline, bust tie
    • Adjustable spaghetti straps
    • Stretchy smocked back
    • Ruffled skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5499

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Fun High Rise Striped Knit Midi Skirt

    Give your vacay style a dynamic upgrade in this flirty knit midi skirt perfect for a getaway or weekend fun! The skirt boasts a high-rise waist, a bodycon fit, a center back slit for movement, and a midi-length hem on pointelle knit fabric showcasing a trendy striped pattern. Complete the look with the matching top.

    Shop Matching Top: Flirty Fun V-Neck Tie Striped Knit Crop Top

    Fit & Features

    • Pointelle knit fabric, striped pattern
    • High-rise waist
    • Center back slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1013

    Category Name: Vacation Looks

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Whimsical Muse Chiffon Swiss Dot Skater Dress

    You'll be a chic whimsical muse in this airy chiffon skater dress! The short dress features a square neckline, short billowy puff sleeves with ruffled accents at the shoulders, an open back with an adorable bow tie-back design, and a short skater skirt with a flared-out silhouette. The lined chiffon fabric features an all-over swiss dot pattern. Style this flirty dress with classic block heels.

    Fit & Features

    • Square neckline
    • Short puff sleeves, ruffled accents, elasticized hems
    • Open-back, bow design, tie closure
    • Empire waist, elastic back
    • Short skater skirt, fit and flare silhouette
    • Sheer chiffon fabric, swiss dot pattern, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2288

    Category Name: Vacation Looks

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Follow Your Heart Sleeveless Ruffled Lace Maxi Dress

    Follow your heart and it'll lead you to this lace maxi dress! Perfect for bridal showers, dressy brunches, or parties. This sleeveless dress brings an allure of romance in a square neckline with adjustable spaghetti straps, a stretchy smocked bodice, and a tiered ruffled silhouette. Complete the look in strappy heeled sandals.

    Fit & Features

    • Lace fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • Square neckline
    • Tiered ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3382

    Category Name: Vacation Looks

    Price: $28.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Wild Intentions Cutout Mesh Mini Dress

    Giving an island goddess with a hint of chaos—in the best way. The bodycon fit and hoop cutout bring the heat, while the ruffle-trim slit? Pure drama.

    Fit & Features

    • Mesh-lined fabric with leopard multi-print
    • Cowl halter neckline with spaghetti straps
    • Side cutout with hoop insert detail
    • Bodycon fit with asymmetric ruffle-trim slit
    • Mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000144

    Category Name: Vacation Looks

    Price: $7.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • Shape Shift Resin Square Bangle Bracelet

    Because your stack deserves a statement piece. This resin square bangle adds a bold, modern twist to your wrist game—wear it solo or layer for instant cool-girl points.

    Fit & Features

    • Smooth resin material
    • Square bangle design
    • Solid structured fit
    • Lightweight and comfortable

    Style Number/Barcode: 07003-000113

    Category Name: Vacation Looks

    Price: $3.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free