Vacation Looks

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STYLE SPOTLIGHT

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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.

  • Perfect Always Strapless Cutout Ruffle Maxi Dress

    Have all eyes on you in this strapless maxi dress boasting a sweetheart twist neckline and a cutout bodice. The smooth knit fabric hugs your curves along the form-hugging silhouette and creates a front center ruffle design. 

    Fit & Features

    • Smooth knit lined fabric, moderate stretch
    • Strapless sweetheart twist neckline
    • Cutout bodice
    • Center front ruffle design
    • Form-hugging, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3601

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Back Strapless Strappy Mini Dress

    Make everyone look back at you in this sassy rib knit mini dress! Perfect for summer BBQs or pool parties, this dress boasts a flattering strapless neckline and bust cutout, a strappy back design, and a bodycon fit. Complete the look in sandals and sunnies!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Strappy back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5767

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Blooms Floral Ruffle Chiffon Skater Dress

    Let this tropical floral skater dress bloom into your summer lineup! With a sweetheart neckline featuring delicate ruffle trim, adjustable spaghetti straps and padded bra cups, this skater silhouette will flatter your figure. The mini-length hem adds a flirty touch to this tropical floral printed chiffon dress. Complete the look with a crossbody purse and sandals!

    Fit & Features

    • Tropical floral print
    • Chiffon fabric with woven lining, no stretch
    • Sweetheart ruffle trim neckline
    • Padded bra cups
    • Adjustable spaghetti straps
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3204

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sea You Later Chain Belt

    Giving mermaid off-duty energy. This chain belt brings all the coastal cuteness with starfish and shell accents—wear it poolside, seaside, or whenever you’re channeling beach babe vibes.

    Fit & Features

    • Chain-link design
    • Starfish and shell accents
    • Adjustable fit with lobster clasp closure

    Style Number/Barcode: 07301-000139

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Social Butterfly Charm Necklace

    With an etched butterfly charm on a dainty chain, this necklace is a pretty piece for everyday wear. Complete the look with a stackable ring set.

    Fit & Features

    • Etched butterfly charm
    • Dainty chain
    • Lobster clasp closure

    Style Number/Barcode: 07002-1865

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Cutie Strappy Faux Leather Sandals

    Give off cutie vibes in these floral strappy faux leather sandals! They feature a round toe, an asymmetric strappy design with adorable flower accents with faux pearl center detailing, an adjustable ankle strap and heel strap, and a flat sole for comfortable wear. Style with a flowy summer dress for a perf summer look.

    Fit & Features

    • Faux leather upper
    • Round toe
    • Asymmetric strappy design
    • Flower design with faux pearl center details
    • Adjustable ankle strap, heel strap
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1213

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She’s The Moment Tie-Front Halter Top

    Serving main character energy with every knot—this top is that girl. The halter V-neck and flirty tie-fronts give it an effortlessly hot vibe that’s perf for your next weekend adventure.

    Fit & Features

    • Twill woven fabric
    • Sleeveless halter V-neckline
    • Multi-tie-front design
    • Partially open back
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-000068

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L

  • Prep For Paradise Strapless Tropical Jumpsuit

    Prep yourself for paradise starting with this tropical jumpsuit to pack in your luggage! Made from a smooth knit fabric showcasing a palm tropical print, this jumpsuit features a strapless neckline with side-ruched seams that accentuate, a flattering wide-leg silhouette. Complete the look with sunglasses and sandals!

    Fit & Features

    • Smooth knit fabric, tropical palm print, moderate stretch
    • Strapless neckline
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2520

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Booked And Unbothered Leopard Oversized Sunglasses

    These oversized sunglasses bring instant glam with a bold frame that was made for poolside posing and low-key paparazzi moments.

    Fit & Features

    • Oversized leopard frames with metal trim
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000009

    Category Name: Vacation Looks

    Price: $11.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Vibes High Slit Striped Knit Maxi Dress

    This casual-chic striped knit maxi dress is perfect for your laid-back weekend vibes! Designed with stretchy ribbed knit with a thin striped pattern, it features a sleeveless scoop neckline with spaghetti straps, high-cut side slits on each side for added movement, and a form-hugging slim fit on the maxi-length silhouette. Style this long dress with strappy sandals.

    Fit & Features

    • Striped ribbed knit fabric, short knit lining, moderate stretch
    • Scoop neckline
    • Spaghetti straps
    • High side slits
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5778

    Category Name: Vacation Looks

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lovely Look Cold Shoulder Bodycon Lace Mini Dress

    Nothing can compare to your lovely look in this lace mini dress as a stunning bride-to-be or birthday girlie! Featuring a trendy cold shoulder V-neckline, feminine flutter short sleeve cuffs, and delicate spaghetti straps, this dress hugs your curves for a bodycon fit that will turn heads. Complete the look with earrings and clutch.

    Fit & Features

    • Lace fabric lined with stretchy knit
    • Cold shoulder V-neckline
    • Flutter short sleeve cuffs, spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3423

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flow My Way Chiffon Lace Trim Skater Dress

    Effortlessly flow into any occasion in this simply chic chiffon skater dress - the perfect style for bridal showers, graduates, and birthday girls! The dress features a cold shoulder V-neckline with a delicate scalloped lace trim, adjustable spaghetti straps, short-sleeve cuffs, and a flattering fit-and-flare short-length silhouette. The airy chiffon fabric includes a stretchy knit lining. Complete the look with a sleek choker and earrings.

    Fit & Features

    • Cold shoulder design, V-neckline, scalloped lace trim
    • Adjustable spaghetti straps, short-sleeve cuffs
    • Back zipper and hook-eye closure
    • Fit-and-flare skater silhouette
    • Short-length hem
    • Airy chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2053

    Category Name: Vacation Looks

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Favorite Strapless Cutout Floral Maxi Dress

    Create a stunning aurora in this floral maxi dress for summer cocktail hours! The strapless neckline and side cutout provide a flattering silhouette, while the form-hugging fit accentuates your curves, and the high side slit offers a show of leg. Complete the look in strappy stiletto heels.

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Strapless neckline
    • Side cutout
    • Form-hugging fit
    • High side slit
    • Runs true to size

    Style Number/Barcode: 05101-3278

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Yacht Babe Floral Swim Cover Up

    Soak up the sun looking like a babe in this swim cover-up! Wrap yourself in the beauty of summer with this long cover-up with a gorgeous floral print and a maxi form-hugging silhouette.

    Fit & Features

    • Floral print, sheer mesh stretchy fabric
    • Low-rise waist, side cutouts
    • Form-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 07105-000014

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfectly Glam Rhinestone Butterfly Spiral Strap Sandals

    Create a perfectly glam vibe with these rhinestone butterfly strappy sandals! Designed with sleek faux leather, they feature an almond-shaped toe, a dual toe strap and trendy spiral strap design, mini rhinestone embellishments for that glitzy shine, and organza butterfly accents with rhinestone detailing. They include a flat sole with a padded insole for comfortable wear. Style with a summer party dress!

    Fit & Features

    • Faux leather upper
    • Almond toe
    • Dual toe strap and spiral strap design
    • Mini rhinestones
    • Sheer organza butterfly accents with rhinestones
    • Flat sole, padded insole
    • Runs true to size

    Style Number/Barcode: 07406-0362

    Category Name: Vacation Looks

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Catching Looks Crochet Palazzo Pants

    Serving body and beach energy all in one slay. These crochet palazzo pants feature a high-rise waist and sheer wide-leg silhouette, perf for sipping cocktails, catching sunsets, or just catching looks.

    Shop Matching Top: Catching Looks Crochet Bandeau Tube Top

    Fit & Features

    • Sheer crochet fabric with panty lining
    • High-rise waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-000008

    Category Name: Vacation Looks

    Price: $34.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sun-Kissed Moments Triangle Bikini Top

    You'll have sun-kissed moments in this trendy triangle bikini top featuring the cutest seashell charm at the center of the bust. Style with the matching bikini bottoms.

    Shop Matching Bottoms: Sun-Kissed Moments Tie-Strap Bikini Bottoms

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Triangle-shaped cups
    • Seashell metal charm
    • Adjustable spaghetti straps
    • Tie-back spaghetti straps, beaded details
    • Runs true to size

    Style Number/Barcode: 07104-000006

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Muse Floral Maxi Dress

    Beach date or rooftop night out? You’re covered. With a drapey neckline and bold floral print, this maxi gives you that effortless she’s glowing moment.

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Cowl halter neckline
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000273

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L, XL

  • Simply Adorable Puff Sleeve Cutout Crop Top

    Simply adorable, this puff sleeve cutout crop top will effortlessly elevate your casual 'fits. The smooth knit fabric offers a lightweight feel and plenty of stretch. The top features a ruched V-neckline, short puff sleeves with elasticized hems, and a bold front cutout below the bust. The open lower back is accented with an adorable tie-back design. Style this fitted top with high-rise jeans and strappy mules.

    Fit & Features

    • Stretchy knit fabric, double-lined front
    • Ruched V-neckline
    • Short puff sleeves
    • Front cutout
    • Open lower back, tie-back design
    • Cropped, fitted
    • Runs true to size

    Style Number/Barcode: 06001-5329

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stackable Style Seven Pack Ring Set

    The perfect seven-pack ring set to achieve stackable style! This set features an assortment of various designs and styles with glitzy rhinestone embellishments that bring some sparkle to your look. Complete the look with a chic handbag for any occasion!

    Fit & Features

    • Seven-pack ring set
    • Rhinestone embellishments
    • Various designs and styles

    Style Number/Barcode: 07004-0399

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crusin' The Tropics Lace-Up Tropical Mini Dress

    Cruise the tropics in this stylish tropical mini dress! Designed with a tropical palm print on knit fabric, this dress is sure to stand out on the island and boat. Featuring a V-neckline and spaghetti straps, a lace-up back that lets you customize the style, and a flattering bodycon fit. Complete the look with sunglasses.

    Fit & Features

    • Tropical palm print, stretchy knit fabric, sewn-in lining
    • Spaghetti straps
    • V-neckline
    • Lace-up back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5549

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Whimsical Essence Ruffled Floral Maxi Skirt

    Adorn your look with the whimsical beauty of this ruffled floral maxi skirt in a sleek high-rise waist and a flowy silhouette made for sashaying through flower fields!

    Fit & Features

    • Woven fabric, floral print
    • High-rise waist
    • High front ruffled slit
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06301-0210

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Outside The Lines Tie Back Slit Marble Maxi Dress

    Color outside the lines and rock this chic marble print maxi dress for dressy showers or summer events! With a square neckline and spaghetti straps, this dress flatters your figure with a form-hugging fit. The tie-back design adds a touch of unique style while the front slit showcases your legs along the maxi-length hem. Complete the look with earrings and heels.

    Fit & Features

    • Marble print, smooth knit fabric with stretchy lining
    • Spaghetti straps
    • Square neckline
    • Tie back design
    • Form-hugging fit
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05101-3455

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Constant Sensation V-Neck Corset Satin Skater Dress

    Always be a constant sensation when you step out in this satin skater dress at parties or soirees! With a flirty V-neckline, comfortable shoulder straps, and a flattering corset-seam bodice, this dress has a playful skater silhouette and a short-length hem. The abstract print adds a touch of fun to the satin fabric. Complete the look with bracelets and a clutch!

    Fit & Features

    • Abstract print, satin fabric, woven lining, no stretch
    • V-neckline, shoulder straps
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3291

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale