Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

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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.

  • Ardell Demi Wispies Lashes 5 Pack

    Glam up your eyes with these gorgeous lashes. The Ardell Demi Wispies lashes offer a natural, long feathered and glamorous look, are easy to apply, and are even reusable! Perfect for your next sexy night out outfit like a sultry crop top and mini skirt. The lashes work best for large and deep-set eyes. Don't forget to pick up the eyelash glue! 

    Fit & Features

    • Long, feathered natural look
    • Reusable 
    • Includes 5 sets of eyelashes
    • Eyelash glue sold separately

     

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07307-0372

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beautiful Bliss Floral Sequin Mesh Babydoll Dress

    Get swept up in the beauty of this babydoll dress perfect for brides-to-be, wedding showers, and dressy soirees! The sheer 3/4 length puff sleeves and square neckline add a touch of romance, while the babydoll silhouette and short hem create a playful and flirty look. The floral embroidery and sequins on the sheer mesh overlay add a touch of whimsy to this stunning dress. Complete the look with a chic ring set and heels!

    Fit & Features

    • Sheer mesh overlay line with woven fabric
    • Floral embroidery, sequin embellishments
    • Back zipper and hook-eye closure
    • Babydoll silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3357

    Category Name: Vacation Looks

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic And Sleek Square Strappy Flat Sandals

    Chic and sleek! These flat sandals offer endless styling options with sleek dual straps and a statement square accent, they're perfect for day or night fun.

    Fit & Features

    • Square toe 
    • Dual straps, square accent
    • Flat sole with trim
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-000009

    Category Name: Vacation Looks

    Price: $18.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: 6, 6.5

  • Stunning Sparkle Large Hoop Earrings

    Give off a stunning sparkle when these hoops catch the light! These hoop earrings feature beautiful crystal-like details to top off all your looks with a bit of bling. Topped with post-back closures for easy wear. Style these sleek hoops with a chic bodysuit and high waist jeans for an effortlessly put-together look.

    Fit & Features

    • Large hoop design
    • Cyrstal-like details 
    • Post-back closure

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-0105

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vintage Mood Activated Retro Sunglasses

    These retro-inspired oval sunglasses give your fit an instant upgrade—perfect for rooftop brunches, low-key flexes, and celeb-off-duty moments.

    Fit & Features

    • Oval lens shape with slim metal frame
    • Nose support pads
    • 100% UV protection
    • Retro-inspired silhouette

    Style Number/Barcode: 07008-000012

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Here To Slay One-Shoulder Cutout Knit Crop Top

    This iconic crop top was here to stay and slay your 'fits! Made with a stretchy ribbed knit fabric, it features an asymmetric one-shoulder neckline with a tank strap, a trendy twist-front design and sultry center bust cutout, and a cropped hem with a form-hugging fit for a snatched look. Style with high-rise jeans and sneakers for a cute and casual vibe!

    Fit & Features

    • Stretchy ribbed knit fabric
    • Asymmetric one-shoulder neckline, tank strap
    • Twist-front design
    • Bust cutout
    • Cropped
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06002-1950

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beach Goddess Crochet Lace-Up Maxi Dress

    She’s giving beach goddess vibes from brunch to golden hour cocktails. This crochet maxi hugs your curves with a bodycon fit and an open lace-up back that’s totally Insta-worthy.

    Fit & Features

    • Crochet lined fabric
    • V-neckline
    • Spaghetti straps
    • Open lace-up back design
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000072

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Hello Summer V-Cut Bikini Bottoms

    Say hello to summer in these trendy bikini bottoms featuring a V-cut waist, scrunched detailing at the back, and a thong fit. Pair with the matching bikini top for a pool party.

    Shop Matching Top: Hello Summer Triangle Bikini Top

    Fit & Features

    • Nylon-blend fabric, high stretch
    • V-cut waist
    • Scrunched back
    • Thong fit
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000011

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED, SLATE

    Available Size: L

    Product Badge:
    • Sale
  • Right Impression V-Neck Floral Ruffle Skater Dress

    A cutie like you will always make the right impression in this floral skater dress on dates or at brunch!  Featuring sheer peasant long sleeves and a flattering V-neckline, this skater silhouette is completed with a ruffled short-length hem. The V-cut back with a spaghetti strap tie adds a touch of allure. Style this floral skater dress with block heels.

    Fit & Features

    • Floral print, chiffon fabric with woven lining, no stretch
    • V-neckline, V-cut back with spaghetti strap tie
    • Skater silhouette
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-2894

    Category Name: Vacation Looks

    Price: $6.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Summer Daze Strappy Block Heels

    Put them all in a daze with the chic details of these stunning strappy block heels! They feature an open square-shaped toe, a criss-cross strappy design across the foot, thin adjustable ankle and heel straps with a buckle closure, and a block heel. Style with a mini handbag.

    Fit & Features

    • 4" Block heel
    • Open square toe, criss-cross strappy design
    • Adjustable ankle and heel straps with buckle closure
    • Padded insole
    • Coral and yellow heels are faux leather
    • Black heels are faux nubuck
    • Runs true to size

    Style Number/Barcode: 07401-4926

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heat Wave Halter Bandeau Bikini Top

    Bring the heat to your summer vacay in this bandeau bikini top featuring a metal rectangular accent and halter tie-back straps. Pair with the matching bikini bottoms.

    Shop Matching Bottoms: Heat Wave V-Cut Bikini Bottoms

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Sweetheart bust
    • Metal rectangular accent
    • Halter tie-back spaghetti straps
    • Lower tie-back straps
    • Runs true to size

    Style Number/Barcode: 07104-000004

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Darling Delight Sleeveless Lace Trim Skater Dress

    When the occasion calls for flair, this sleeveless skater dress delivers with darling delight! Perfect for bridal showers, rehearsal dinners, and graduations. Made from a smooth chiffon fabric, the lace trim straps and hem add a delicate touch. Featuring a square neckline and ruched bust, the flattering skater silhouette will have you twirling all day! Complete the look in block heels.

    Fit & Features

    • Smooth chiffon fabric, stretchy knit lining
    • Square neckline, lace trim straps
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Lace trim short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3563

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • More To Come Twist Tube Crop Top

    Elevate your look with this tube top perfect for everyday styling! It boasts a twist strapless neckline and a fitted crop hem that flaunts your figure.

    Fit & Features

    • Rib knit stretchy fabric
    • Strapless tube sweetheart neckline
    • Twisted bust
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000211

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: RED, BLACK

    Available Size: S, M, L, XS

  • Style Icon Strappy Faux Leather Short Block Heels

    These chic strappy short block heels are a must-have for a style icon like you. Designed with smooth faux leather material, they feature a short block heel for comfortable wear, an open square toe, an asymmetric strappy design across the foot, and adjustable ankle and heel straps for a customized fit. Style with classic hoop earrings.

    Fit & Features

    • 2.5" Block heel
    • Faux leather upper, subtle padded insole
    • Open square toe
    • Asymmetric strappy design
    • Adjustable ankle and heel straps with buckle closure
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4661

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cross My Heart Layered Necklace

    Elevate your style with this layered necklace perfect for accessorizing your outfit. This unique necklace features a layered design with a delicate cross and heart charms. Complete the look in a chic matching set for weekend plans!

    Fit & Features

    • Layered necklace
    • Cross and heart charms
    • Lobster clasp closure

    Style Number/Barcode: 07002-1837

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • New Heights Cork Platform Wedges

    Take your look to new heights with these cork platform wedges, perfect for shower celebrations, graduations, or vacay!

    Fit & Features

    • Wedge heel
    • Round toe, curved toe strap
    • Platform sole
    • Cushioned insole
    • Adjustable ankle strap, buckle closure
    • Cork and faux leather material
    • Runs true to size

    Style Number/Barcode: 07406-0365

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: 7.5, 8

    Product Badge:
    • Best Seller
  • Gorgeous Arrival Rose Floral Chiffon Maxi Dress

    Make a gorgeous arrival in this rose floral chiffon maxi dress for showers, birthdays, or family parties! The sweetheart neckline and adjustable spaghetti straps provide a flattering and comfortable fit, while the padded bra cups offer support and shape. The maxi-length hem and high front slit add a touch of sultry, making you feel so beautiful! Complete the look in chic wedge sandals and sunnies.

    Fit & Features

    • Rose floral print
    • Chiffon fabric lined with stretchy knit
    • Padded bra cups, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • High front slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3128

    Category Name: Vacation Looks

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Vacay Lace-Up Tropical Maxi Dress

    Your summer vacay needs this tropical maxi dress! Made from a stretchy knit fabric adorned with a tropical print, this maxi dress features a flattering cowl neckline, spaghetti straps, and a lace-up back for head-turning allure. The form-hugging fit flaunts your figure while the high side slit offers a show of leg. Complete the look with sunglasses and a cocktail in hand!

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Cowl neckline
    • Spaghetti straps, lace up back
    • Form-hugging fit
    • High side slit
    • Maxi length hem
    • Runs true to size

    Style Number/Barcode: 05102-5743

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Serenade Me V-Neck Crop Top

    A dreamy look awaits in this sleeveless top with a flattering V-neckline and fitted crop hem that flaunts your figure. Pair with the matching skirt to complete the look!

    Fit & Features

    • Double-lined smooth knit stretchy fabric
    • V-neckline
    • Wide shoulder straps
    • Fitted crop hem
    • Runs true to size

     

    Shop The Matching Skirt: Serenade Me Bodycon Midi Skirt

    Style Number/Barcode: 06001-000042

    Category Name: Vacation Looks

    Price: $19.90

    Availability: In Stock

    Available Color: BLACK, MOCHA

    Available Size: M, L, S

    Product Badge:
    • Part of a Set
  • Dreaming Of Paradise Cowl Neck Tropical Midi Dress

    Let your vacation or getaway be filled with sand and compliments when you're in this tropical midi dress! Featuring a cowl neckline and adjustable spaghetti straps for a perfect fit, this bodycon dress also boasts a side slit and midi-length hem. Complete the look with sunglasses and sandals!

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Adjustable spaghetti straps
    • Cowl neckline
    • Bodycon fit
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-5613

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Happy Hour High-Rise Slit Midi Skirt

    Embrace the sultry vibes of this high-rise slit midi skirt for your next happy hour spree! Pair with the matching top to complete the vibe.

    Shop Matching Top: Always Happy Hour Cowl Neck Crop Top

    Fit & Features

    • Double-lined slinky knit stretchy fabric
    • High-rise waist
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000024

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: GREEN, RUST

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Hit The City Strapless Slit Crop Top

    Throw on your sunnies and hit the city in this strapless crop top for a flirtatious style! The top boasts a trending strapless sweetheart neckline, a center front adjustable drawstring and slit, and a ruffled trim crop hem. Complete the look in denim jeans and sneakers!

    Fit & Features

    • Brushed knit soft fabric, moderate stretch
    • Strapless sweetheart neckline
    • Center front adjustable drawstring
    • Center slit design
    • Ruffled trim cropped length
    • Runs true to size

    Style Number/Barcode: 06001-5375

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Howdy Hey Twist Braided Straw Cowboy Hat

    Tip your hat to everyone in this stylish straw cowboy hat at festivals, concerts, or bachelorettes! It's designed with a curved wide brim with a braided twist trim, and adjustable inner strings to get a snug fit. Complete the look with cowboy boots.

    Fit & Features

    • Braided twist trim
    • Wide curved brim
    • Inner adjustable strings
    • Straw material

    Style Number/Barcode: 07302-1642

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Catching Looks Crochet Bandeau Tube Top

    Serving body and beach energy all in one slay. This crochet bandeau tube top features a strapless sweetheart neckline and chic tie-front design, perf for sipping cocktails, catching sunsets, or just catching looks.

    Shop Matching Bottoms: Catching Looks Crochet Palazzo Pants

    Fit & Features

    • Sheer textured crochet fabric with lining
    • Strapless sweetheart neckline
    • Flow tie-front design at the bust
    • Fitted ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-000048

    Category Name: Vacation Looks

    Price: $19.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: M

    Product Badge:
    • Part of a Set