Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

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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.

  • Ray Of Sunshine Eyelet Lace Bustier

    Look and feel like a ray of sunshine in this eyelet bustier for a flirty day date or weekend plans! The bustier is designed to snatch your figure while the ruffled crop hem adds the prettiest look to your favorite denim shorts.

    Fit & Features

    • Eyelet lace woven fabric
    • Sweetheart neckline
    • Adjustable shoulder straps
    • Front hook and eye fasteners
    • Stretchy smocked back
    • Ruffled crop hem
    • Runs true to size

    Style Number/Barcode: 06003-2767

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S

    Product Badge:
    • Sale
  • Kacey Formal Halter Pleated Long Dress

    Special Occasion

    Serve pure bliss in the Kacey formal dress designed for twirling all night at a wedding reception, banquet, or gala! She features an adorable halter neckline with a tie-back closure, an open-back, and a pleated flowy long-length silhouette. The formal dress is composed of a plisse airy fabric with no stretch. Complete your dressy look with a stunning hair accessory for a glam updo and lace-up heels.

    Fit & Features

    • Sleeveless halter neckline, tie-back closure
    • Adhesive bra recommended
    • Open-back design
    • Hidden back zipper closure
    • Pleated, flowy, long-length silhouette
    • Plisse airy fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05002-3182

    Category Name: Vacation Looks

    Price: $9.97 $79.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fawn Over You Marble Print Chiffon Skater Dress

    You'll be fawned over when in this marble print chiffon skater dress! From the adjustable spaghetti straps to the flattering square neckline, this dress has got you covered. The stretchy smocked bodice creates a comfortable and perfect fit, while the tie waist belt accentuates your curves. With a playful ruffled tiered short-length hem, this dress is perfect for twirling! Complete the look in wedges for a dressy occasion.

    Fit & Features

    • Marble print, chiffon lined fabric
    • Adjustable spaghetti straps
    • Square neckline
    • Tie waist belt, ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3081

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Pretty Cute Floral Skater Short Dress

    Nothing comes as close to cute as this floral skater dress! Perfect for shower celebrations or afternoon teas, this short dress boasts a pretty corset-inspired bodice and a voluminous hem.

    Fit & Features

    • Floral print, cotton woven fabric, tulle and woven linings
    • Square neckline, bust tie
    • Wide shoulder straps
    • Back zipper and hook-eye closure
    • Corset-inspired bodice, pleating
    • Skater silhouette, short-length hem, pleated trim
    • Runs true to size

    Style Number/Barcode: 05101-4037

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Style Belted Twill Skort

    Show off a trendy style this summer season with this of-the-moment twill skort. It features a mid-rise waist with an adjustable faux leather belt, a hidden side zipper closure, a front skirt overlay with pleated detailing, shorts, and a fitted silhouette. Pair with a graphic tee and booties for a cool vibe.

    Fit & Features

    • Mid-rise waist, belt loops
    • Adjustable faux leather belt, rectangular buckle
    • Hidden side zipper closure
    • Front skirt overlay, pleating, shorts
    • Fitted silhouette
    • Smooth twill fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06303-0238

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Glam Espadrille Sequin Fringe Sandals

    Slip into these espadrille sequin fringe sandals to glam up to your summer looks! Designed with a braided espadrille material, they feature a round toe, a wide strap across the foot with woven embroidery, shimmering sequins, and trendy fringe trims, and a flat sole. The open back offers effortless on-and-off styling. Pair with your flowy sundresses to create fabulous 'fits for your weekend plans!

    Fit & Features

    • Espadrille upper material
    • Round toe
    • Wide strap
    • Woven embroidery, sequins, fringe trims
    • Open back, flat sole
    • On-and-off styling
    • Runs true to size

    Style Number/Barcode: 07404-1209

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Adoring Style V-Neck Tie Eyelet Skater Romper

    Chanel this adoring and stylish eyelet skater romper for sweet summer looks at BBQs and Fourth of July parties! The V-neckline, spaghetti straps, and surplice bust provide a flattering fit, while the tie-back design adds a touch of sophistication. The skater silhouette and flowy short-length hem create an effortlessly chic look. Complete the look in wedge sandals.

    Fit & Features

    • Eyelet knit fabric, moderate stretch
    • V-neckline
    • Spagehtti straps
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 06503-1124

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Days Floral Halter Skater Dress

    Sunny days call for this cute floral skater dress featuring tie-back straps and a breezy fit-and-flare silhouette!

    Fit & Features

    • Rayon woven fabric
    • Floral print
    • Sleeveless V-neckline
    • Tie-back halter straps
    • Open back, lower tie-back design
    • Short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5874

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RUST

    Available Size: L, XS

    Product Badge:
    • Sale
  • Kick Up The Style Cowboy Boots

    Kick the dust off in these stylish faux leather cowboy boots perfect for music festivals and country bars! They feature a pointed toe, stacked block heel, classic western-inspired stitched designs, and a curved mid-length shaft with pull tabs to easily slide on and off. Complete the look in a fringe cowboy hat.

    Fit & Features

    • Pointed toe
    • Stacked block heel
    • Classic western-inspired stitched designs
    • Mid-length shaft, pull tabs
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1620

    Category Name: Vacation Looks

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take Me Away Crochet Tunic Sweater

    Look good on the go in this crochet tunic sweater for your upcoming trip! Designed on sheer crochet fabric, it features long sleeves with chic flare cuffs, a crew neckline, and a sultry open-back design. Finished with a form-hugging fit and short-length hem. Style with sleek hoop earrings. 

    Fit & Features

    • Long sleeves, flare cuffs
    • Crew neckline
    • Open back design
    • Form-hugging 
    • Short-length 
    • Sheer crochet fabric
    • Runs true to size

    Style Number/Barcode: 06005-1828

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Vibe Rhinestone Star Clear Shield Sunglasses

    Channel that iconic early 2000s vibe with these fabulous clear shield sunglasses! They feature a wide shield design with a flat top, sleek metal and plastic arms with trendy cutout detailing, mini rhinestones and star accents at each side, rubber nose pads, and clear lenses. Style with hoop earrings and a mini handbag.

    Fit & Features

    • Shield design with flat top
    • Metal and plastic arms, cutout detail
    • Mini rhinestones, star detail
    • Metal nose bridge, rubber nose pads
    • Clear lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1078

    Category Name: Vacation Looks

    Price: $3.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Summer Striped Crop Top

    The most effortless yet adorable crop top for summer! Flaunt your figure in this striped top with a trendy halter neckline and fitted silhouette perfect for styling with shorts.

    Fit & Features

    • Striped pattern, stretchy rib knit fabric
    • Halter neckline, spaghetti strap ties
    • Ruched bust
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06005-000003

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LIGHT, BLUE, RED

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Drop It Low Rise Bootcut Denim Jeans

    Pop, lock, and drop it down in these low-rise denim jeans to give your style a cute throwback vibe! They feature a hip-hugging fit, and a bootcut silhouette, and are composed of premium medium-wash denim with color fading and slight stretch. Complete the look in a flirty crop top and your favorite sneakers!

    Fit & Features

    • Low-rise waist
    • Hip-hugging fit
    • Bootcut silhouette
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Premium medium wash denim, slight stretch, color fading
    • Runs true to size

    Style Number/Barcode: 06602-0440

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Make It Chic Tube Top

    This strapless tube top moment hugs you just right with ruched details for that elevated off-duty model look.

    Fit & Features

    • Smooth knit fabric with subtle sheen
    • Strapless tube folded neckline
    • Ruched details
    • Fitted hem
    • Runs true to size

    Style Number/Barcode: 06001-000230

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: L

  • Western Babe Cow Print Mini Skirt

    Make the room say, "Yeehaw" looking like a sassy western babe! Create your perfect party outfit in this cow print mini skirt featuring a high-rise waist, bodycon fit, and a slit accent. The skirt is composed of french terry knit fabric with plenty of stretch. Complete the look with a faux leather bustier and accessories.

    Fit & Features

    • High-rise waist
    • Bodycon silhouette
    • Slit accent
    • Mini-length hem
    • Cow print
    • Lined french terry knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0697

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Outside The Lines Floral Print Maxi Skirt

    Style outside the lines and go for a bold chic look in this floral print maxi skirt. Style with the matching top for a complete look.

    Shop Matching Top: Outside The Lines Floral Print Crop Top

    Fit & Features

    • Bold floral print, lined stretchy knit fabric
    • High-rise waist
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-1123

    Category Name: Vacation Looks

    Price: $36.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Throwback Babe Side Slit Mini Skort

    Bring on the throwback vibes with this stylish mini skort! It's designed with a high-rise waist, front slit, and a hidden back zipper with a mini skirt overlay and shorts lining. Wear with a crop top to embrace the '90s look.

    Fit & Features

    • High-rise waist 
    • Back zipper closure
    • Form-hugging, front slit
    • Mini skirt overlay
    • High-waist shorts
    • Smooth woven fabric, minimal stretch
    • Runs true to size 

    Style Number/Barcode: 06403-0188

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Babe Alert Scoop Neck One-Piece Swimsuit

    Fit & Features

    • Smooth nylon-blend fabric with contrast trim, plenty of stretch
    • Scoop neckline, adjustable spaghetti straps
    • Low back
    • High-cut design, cheeky bottom
    • Form-hugging fit
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-0871

    Category Name: Vacation Looks

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fly With Me Butterfly Crochet Crop Top

    You'll fly in this butterfly crochet crop top at festivals, concerts, and any kind of fun in the sun!

    Fit & Features

    • Crochet fabric
    • Halter neckline, spaghetti strap ties
    • Padded bra cups
    • Butterfly design
    • Open back with spaghetti strap tie
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-2758

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • City Chic Ruffled Midi Dress

    Step out like a scene straight out of a rom-com in a midi dress that gives major butterflies!  The city-chic midi dress features a sleeveless square neckline, spaghetti straps that lead to a cross-strap design, and a high side slit on the left leg with a romantic ruffled trim. The relaxed fit waist leads to a midi-length A-line silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps, cross-back design
    • Strapless bra friendly 
    • High side slit, ruffled trim
    • Relaxed fit waist, A-line silhouette
    • Midi-length hem 
    • Smooth knit fabric 
    • Form-hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05101-1038

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Blossom Sweetheart Floral Mesh Mini Dress

    Your amount of admirers will blossom when they see you in this sultry floral mesh mini dress! This flirty mini dress features a sweetheart neckline and padded bra cups for a flattering fit. Its adjustable spaghetti straps and ruched seams ensure the perfect bodycon silhouette. Complete the look in block heels.

    Fit & Features

    • Floral print, mesh fabric, sewn-in knit lining, moderate stretch
    • Sweetheart neckline
    • Adjustable spaghetti straps, padded bra cups
    • Back zipper and hook-eye closure
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5478

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's A Wildflower Strappy Back Maxi Dress

    Florals, fits, and full-on main character vibes. This floral mesh maxi dress hugs you in all the right places with a flirty strappy back and a vacay allure! 

    Fit & Features

    • Floral print, mesh fabric, soft stretchy knit lining
    • V-neckline
    • Bungee strappy open back
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000097

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Cool Meter Mid-Rise Parachute Cargo Pants

    These parachute cargo pants have a high rating on the cool girl meter! They feature an elasticized mid-rise waist with side adjustable drawcords, side flap pockets with button closures, a loose-fit silhouette, and an adjustable drawcord hem. Style with a basic crop top for a movie night with friends!

    Fit & Features

    • Mid-rise elasticized waist, side adjustable drawcords
    • Side flap pockets, button closures
    • Loose-fit silhouette
    • Adjustable drawcord hem
    • Lightweight nylon woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0745

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylishly Sweet Smocked Tube Skater Dress

    Stylishly sweet, this smocked tube skater dress is perfect for weekend brunch! It features a strapless straight neckline, a V-shaped waist, and a short A-line silhouette for that flirty flair.

    Fit & Features

    • Poplin cotton-blend woven fabric, stretchy knit lining
    • Strapless straight-across neckline
    • Stretchy smocked bodice
    • V-shaped waist
    • Pleating
    • Short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000049

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: XS, S, M, L

    Product Badge:
    • Sale