Vacation Looks

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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.

  • On Island Time Strapless Floral Romper

    This strapless romper exudes carefree vibes, perfect for vacations! The strapless neckline and form-hugging fit accentuate your curves, while the statement floral print adds a touch of tropical essence.

    Fit & Features

    • Stretchy knit fabric, statement floral print
    • Strapless neckline
    • Form-hugging fit
    • Ruffled hem, fitted knit shorts
    • Runs true to size

    Style Number/Barcode: 06503-000053

    Category Name: Vacation Looks

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Iconic Basic Cap Sleeve Midi Dress

    An iconic basic midi dress your closet needs! Create effortlessly chic looks with this knit dress featuring cap sleeves, a V-neck, and a bodycon silhouette with a curved hemline on brushed stretchy fabric. Style with slide sandals and sunglasses for hanging downtown with friends!

    Fit & Features

    • Cap sleeves
    • V-neck
    • Bodycon silhouette
    • Curved midi-length hemline
    • Brushed stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05101-2530

    Category Name: Vacation Looks

    Price: $5.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Eye-Catching Cutout Strappy Slide Sandals

    Slip into these cutout strappy slide sandals for an eye-catching look this season!

    Fit & Features

    • Round toe
    • Strappy cutout design
    • Adjustable strap
    • Slide on-and-off styling
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1277

    Category Name: Vacation Looks

    Price: $25.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: 6, 6.5, 7

  • Wild Instincts Halter Cutout Leopard Mesh Midi Dress

    Elevate your fierce style in this leopard mesh midi dress for a chic cocktail bar. Adorned with a chain-trimmed halter strap, this dress features a sultry cutout bodice with a hoop insert and ruffled trim slit that shows some skin.

    Fit & Features

    • Leopard floral print, mesh fabric, sewn-in knit lining
    • Cowl halter neckline, chain trim, spaghetti strap tie
    • Cutout bodice, hoop insert
    • High side ruffled slit
    • Form-hugging silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000126

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Fling Heart-Shaped Sunglasses

    Flirt up a storm in these adorable heart-shaped sunglasses perf for the summer season. They feature a heart-shaped design with no frame, pink gradient-tinted lenses, sleek metal arms, and rubber nose pads for support. Style with rhinestone hoops.

    Fit & Features

    • Heart-shaped design, no frame
    • Pink gradient-tinted lenses
    • Thin metal arms
    • Rubber nose pads
    • 100% UV protection

    Style Number/Barcode: 07008-1036

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Big Mood Tortoiseshell Oversized Sunglasses

    Giving off that “who is she?” energy in the best way. These oversized sunglasses bring effortless cool to your sunny day 'fits, from pool hangs to city strolls.

    Fit & Features

    • Oversized square-shaped design
    • Tortoiseshell thin metal frame
    • Thin arms
    • Flexible rubber nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000051

    Category Name: Vacation Looks

    Price: $5.97 $11.90

    On Sale: Yes

    Availability: In Stock

    Available Color: TORTOISE

    Available Size: NS

    Product Badge:
    • Sale
  • Too Cute Energy Strapless Paisley Satin Crop Top

    This paisley satin crop top is the easiest way to add a cute boho vibe to your look! The strapless neckline and tie-back closure provide a flattering fit, while the stretchy smocked lining offers comfort and the crop hem flaunts your figure. Complete the look in cute jean shorts and sandals.

    Fit & Features

    • Paisley print, satin fabric, stretchy smocked lining
    • Strapless neckline
    • Tie-back closure
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2550

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Barefoot Bliss Strapless Crochet Maxi

    Sun, sand, and this dress—name a better trio. The strapless twist neckline and open-knit crochet bring breezy beach goddess vibes with zero effort required. Perfect for sunset cocktails on vacay or a beach date!

    Fit & Features

    • Crochet fabric, knit lining
    • Strapless twist neckline
    • Curve-hugging fit
    • Center back slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000011

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Looking Sensational Smooth Knit Maxi Dress

    Rise to the occasion looking sensational in this basic smooth knit maxi dress perfect for dressing up or down! It features a sleeveless scoop neck, sleek spaghetti straps, a bodycon silhouette, and a flirty back-slit accent composed of double-lined smooth knit fabric. Complete the look in lucite mules for a bridal shower or casual party!

    Fit & Features

    • Sleeveless scoop neck, spaghetti straps
    • Bodycon silhouette
    • Back slit accent
    • Maxi-length hem
    • Double-lined smooth knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5158

    Category Name: Vacation Looks

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Sun Tropical Tie Front Crop Top

    The perfect tropical crop top to enjoy the island sun on vacation! Featuring a V-neckline, adjustable spaghetti straps, and a trendy tie-front design, this top is perfect for warm weather while the cropped hem and tropical print add a touch of flirty fun! Complete the look with the matching bottoms.

    Shop Matching Bottoms: Island Sun Tropical High Rise Palazzo Pants

    Fit & Features

    • Tropical print, knit fabric
    • Adjustable spaghetti straps
    • V-neckline
    • Tie front design
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5160

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Golden Hour Tube Top Energy

    She’s luxe, bold, and lowkey lethal. With gleaming metal hardware and a tropical print that’s giving goddess getaway, this tube top brings the heat wherever you wear her—beach club or rooftop takeover. Pair with the matching bottoms.

    Shop Matching Bottoms: Golden Hour Wide Leg Pants Energy

    Fit & Features

    • Tropical print, stretchy knit fabric
    • U-cut out strapless tube neckline, hardware insert
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-000153

    Category Name: Vacation Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Time To Refresh Flocked Mesh Mini Dress

    This chic mini dress will refresh your wardrobe for the season! It features a sleeveless V-neckline, adjustable spaghetti straps for a customized fit, all-over ruching for a flattering look, a mini-length hem, a bodycon silhouette that will hug your curves, and a flocked velvet design in a pretty scroll pattern on mesh fabric. Style this mini-length dress with rhinestone fringe earrings and platform heels.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, back zipper, hook and eye closure
    • All-over ruching
    • Mini-length hem, bodycon fit
    • Flocked velvet design, scroll pattern
    • Sheer mesh fabric, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2384

    Category Name: Vacation Looks

    Price: $5.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Era Oversized Square Sunglasses

    Enter your trendy era with these fabulous oversized shades! The sunglasses feature an angled square-shaped design with a plastic frame, built-in nose pads, a sleek gold metal nose bridge, small studded accents on each side, and ombre-tinted lenses. Style with hoop earrings and a charm necklace.

    Fit & Features

    • Oversized angled square-shaped design
    • Plastic frame
    • Built-in nose pads
    • Gold metal nose bridge
    • Small studded accents
    • Ombre-tinted lenses

    Style Number/Barcode: 07008-1092

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Total Doll Ruffle Mini Skirt

    Step out looking like a fashion icon in this ruffle mini skirt, perfect for a haute night out! Pair with the matching top to complete the look.

    Fit & Features

    • Stretchy knit fabric
    • Mid-rise waist
    • Bodycon silhouette
    • Ruffled mini-length hem
    • Runs true to size

     

    Shop The Matching Top: Total Doll Halter Crop Top

    Style Number/Barcode: 06501-000026

    Category Name: Vacation Looks

    Price: $22.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Spring Forward Chiffon Puff Sleeve Skater Dress

    Spring forward and add this adorable skater dress to your wardrobe! The short dress features a square neckline with ruching at the bust, short puff sleeves, an empire waist seam, an open back with a tie-back accent, and a short skater skirt with a flirty fit and flare silhouette. The airy chiffon fabric provides a lightweight feel. Style with strappy mules.

    Fit & Features

    • Square neckline, ruched bust
    • Short puff sleeves, elastic cinched hems
    • Empire waist seam
    • Open back, tie-back accent
    • Short skater skirt, fit and flare silhouette
    • Sheer chiffon fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2024

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stun And Only Mock Neck Floral Mesh Mini Dress

    Leaving people speechless is easy with this floral mesh mini dress! Crafted from a mesh fabric showcasing a cute floral print perfect for mixing it up this season. This dress features sheer fitted long sleeves with slit flare cuffs, a stylish mock neck, and a flattering bodycon fit. The mini-length hem adds a touch of sass to this stunning dress. Complete the look in stiletto heels.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Mock neck
    • Sheer long sleeves with slit flare cuffs
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5698

    Category Name: Vacation Looks

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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, L

    Product Badge:
    • Part of a Set
  • Sweet Ditsy Floral Eyelet Strapless Mini Dress

    Keep your summer brunch vibe sweet and stylish in this floral eyelet strapless mini dress! The airy lightweight eyelet knit fabric is detailed with a flirty ditsy floral print and features a brushed knit lining for coverage. The mini-length dress is shaped with a strapless straight-across elasticized neckline for added stretch and a bodycon silhouette to highlight your curves. Pair with espadrille wedges and a mini handbag.

    Fit & Features

    • Ditsy floral print
    • Stretchy eyelet knit fabric with knit lining
    • Strapless straight neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5800

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetheart Certified Halter Skater Dress

    Look sweet as can be in this skater dress and turn heads at shower celebrations or parties. The flattering halter square neckline accentuates your shoulders while the playful skater silhouette creates a feminine flare that moves with you.

    Fit & Features

    • Poplin woven fabric, stretchy knit lining
    • Square halter neckline, ponte knit bodice
    • Back zipper hook-eye closure
    • Skater silhouette, hidden side pockets
    • Short length hem
    • Runs true to size

    Style Number/Barcode: 05101-000040

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: YELLOW, BLACK

    Available Size: XS, S, M, L

  • Party Scene Sweetheart Mini Dress

    Steal the scene at every party in this sweetheart mini dress! It features a sleeveless sweetheart neckline, a padded underwire bust tie-shoulder straps, a bodycon silhouette, and side and back ruched seams to accentuate your curves. The smooth knit fabric offers plenty of stretch. Style this mini-length dress with chic earrings.

    Fit & Features

    • Sleeveless sweetheart neckline, padded underwire bust
    • Tie-shoulder straps
    • Back zipper and hook-eye closure
    • Short, bodycon silhouette
    • Side and back ruched seam
    • Knit fabric, lined bodice, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05103-5259

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Girly Twirl Bow Short Sleeve Tee

    Twirl your hair and bring the aesthetic with this adorable short sleeve tee perfect for coquette girlies! This tee features short sleeves and a crew neckline, embroidered bow adds a touch of sass, while the fitted crop hem and stretchy rib knit fabric create a flattering silhouette. Complete the look in a lace trim mini skirt.

    Fit & Features

    • Stretchy rib knit fabric
    • Crew neckline
    • Embroidered bow
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-1836

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stroll The Beach V-Neck Floral Paisley Maxi Dress

    Wherever your summer travels take you, always be in style with this casual floral paisley maxi dress! Featuring adjustable spaghetti straps and a stretchy smocked V-neckline, you'll have the perfect fit for a day in the sun. The crisscross back adds a playful touch, while the ruffled hem gives a flirty flair to the flowy silhouette. Complete the look with a cute hair accessory and sandals!

    Fit & Features

    • Floral paisley print, woven fabric, stretchy knit lining
    • Adjustable spaghetti straps, crisscross back
    • Stretchy smocked V-neckline
    • Flowy silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5566

    Category Name: Vacation Looks

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Eyes On You Lace-Up Slit Maxi Dress

    Not just a dress—this is the moment. From date nights to rooftop dinner parties, this linen maxi dress boasts a cutout bodice and leg-baring slit that does all the flirting for you!

    Fit & Features

    • Gauze linen-blend woven fabric, stretchy knit lining
    • Halter neckline, spaghetti strap ties
    • Lace-up back
    • Cutout accents
    • High front slit
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000053

    Category Name: Vacation Looks

    Price: $48.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M

  • Sparkly Flirt Satin Heatstone Corset

    Sparkly and flirty, add this femme satin corset for a stunningly sultry vibe! It features a sleeveless, sweetheart neck, adjustable spaghetti straps, underbust support, and flexible boning inserts along the bodice with all-over heatstone embellishments. Complete the look in wide-leg pants and heels.

    Fit & Features

    • Sleeveless, sweetheart neck, adjustable spaghetti straps
    • Underbust support
    • Flexible boning inserts
    • All-over heatstone embellishments
    • Cropped hem
    • Back hook-eye closures
    • Sleek satin fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-2059

    Category Name: Vacation Looks

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free