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.

  • Leave An Impression Twist Cutout Knit Midi Dress

    Leaving an impression will be easy with this sleeveless knit midi dress! Perfect for vacation or a weekend spent at the beach, this dress features a flattering scoop neckline, spaghetti straps, a head-turning twist cutout back design, a bodycon fit, and a sultry side slit along the midi-length hem. Complete the look in strappy espadrille wedges.

    Fit & Features

    • Knit fabric, moderate stretch
    • Scoop neckline
    • Spaghetti straps
    • Twist back cutout
    • Side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1950

    Category Name: Vacation Looks

    Price: $17.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artsy Scene Mock Neck Abstract Mini Dress

    Indulge in the artsy scene in this mock neck abstract mini dress for downtown art walks! This sleeveless dress boasts a figure-flattering bodycon silhouette with side ruching, while the mini-length hem adds a flirty touch. The abstract print adds a bold and unique touch to this must-have dress. Complete the look in edgy boots and a shoulder bag.

    Fit & Features

    • Abstract print
    • Mesh fabric, sewn-in knit lining, stretchy
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5630

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Out Of Office One Shoulder Tropical Maxi Dress

    This tropical maxi dress says it's time for vacation! Switch your email to out of office and enjoy a sunny destination in this sleeveless dress featuring a one-shoulder neckline adorned with a knotted shoulder strap, a flattering mermaid silhouette, and a maxi-length hem. Complete the look with sunglasses and a cocktail in hand!

    Fit & Features

    • Tropical palm leaf print, stretchy knit fabric
    • One-shoulder neckline
    • Knotted shoulder strap
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5695

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Legendary Style Western Buckle Faux Leather Sandals

    It's impossible not to make an iconic fashion statement in these faux leather sandals! Featuring a sleek square toe, a flat sole, and a Western-inspired buckle along the strap for added flair. Complete the look with a trendy denim jacket.

    Fit & Features

    • Square toe
    • Flat sole
    • Western-inspired buckle on strap
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1239

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Done In One Ribbed Knit Bodycon Midi Dress

    Be ready in a flash with this done-in-one bodycon midi dress perfect for styling up or down! Made with stretchy ribbed knit fabric, it's also soft and comfortable to wear all day. It features a flattering scoop neckline and tank shoulder straps for a comfortable and stylish fit. With a bodycon silhouette and midi-length hem, this dress will hug your curves! Complete the look in a crop denim jacket and sandals.

    Fit & Features

    • Ribbed knit fabric, sewn-in knit lining, moderate stretch
    • Scoop neckline
    • Tank shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5666

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Garden Glam Floral Maxi Dress

    This isn’t your garden-variety maxi dress, floral abstract print meets daring cutouts and sleek hardware trim for a look that’s equal parts sultry and statement. Perfect for casual celebrations, destination nights, or when you’re ready to own the room.

    Fit & Features

    • Floral Abstract print, mesh-lined stretch fabric
    • Strapless sweetheart neckline, hardware trim
    • Cutout bodice
    • Side ruched seams
    • Curve-hugging, maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000209

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Girlycore Off-The-Shoulder Ruffled Skater Dress

    Embrace a girly-core coquette aesthetic in this skater dress perfect for sunny days! The sweetheart neckline and cutout waist add a flirty touch, while the stretchy smocked bodice hugs your curves, and the ruffled tier short-length hem adds a feminine flair. Complete the look in wedge sandals.

    Fit & Features

    • Airy woven fabric with lining
    • Stretchy smocked bodice with bust tie
    • Cutout waist
    • Ruffled tier skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3054

    Category Name: Vacation Looks

    Price: $10.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cherry On Top Lace Trim V-Neck Mesh Mini Dress

    This mesh mini dress is the cherry on top of your perfect summer! Featuring delicate lace trim V-neckline, adjustable spaghetti straps, and a cherry print on mesh fabric, this mini-length bodycon dress will hug your curves and flaunt your style. Complete the look in platform heels.

    Fit & Features

    • Cherry print, mesh fabric, stretchy knit lining
    • Lace trim V-neckline
    • Adjustable spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5798

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pick Me Halter Floral Eyelet Crop Top

    Pick this floral crop top for the sweetest look! This halter crop top features a flattering V-neckline with a spaghetti strap tie for a perfect fit, while a sweet bow detail adds a touch of charm. The fitted crop hem and floral printed eyelet fabric give off a playful, summertime vibe. Complete the look in high-rise jeans for any casual plans!

    Fit & Features

    • Floral printed eyelet fabric, minimal stretch
    • Halter V-neckline, spaghetti strap tie
    • Bow along the bust
    • Fitted crop length
    • Runs true to size

    Style Number/Barcode: 06001-5365

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Highly Favored Triangle Rhinestone Lariat Necklace

    This lariat necklace will be highly favored over the rest! It features a dainty chain adorned with rhinestone charms leading to a sleek triangle charm with rhinestone trim and a single fringe chain with a rhinestone. Complete the look in a sultry cocktail dress for a rehearsal dinner or reception!

    Fit & Features

    • Dainy chain lariat necklace
    • Rhinestone charms
    • Triangle charm with rhinestone trim
    • Single fringe chain with rhinestone
    • Lobster clasp closure

    Style Number/Barcode: 07002-1872

    Category Name: Vacation Looks

    Price: $2.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Confident Flirty Strappy One-Shoulder Crop Top

    Make your crush stop and stare at you in this sleeveless crop top! It boasts a flirty strappy one-shoulder neckline, and a fitted crop hem, and is made from a stretchy rib knit fabric. Complete the look in a denim mini skirt for any casual plans!

    Fit & Features

    • Stretchy rib knit fabric
    • Strappy one-shoulder neckline
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-1878

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fall Into Fashion Crew Neck Open Back Maxi Dress

    You'll be the cutest thing around in this sleeveless maxi dress all season! With its sleek crew neckline, alluring strappy open back, and flattering form-hugging fit, this dress is both stylish and versatile. Complete with a side slit and maxi-length hem, it's the perfect piece for any occasion. Style this maxi dress with earrings and sandals.

    Fit & Features

    • Stretchy rib knit fabric
    • Crew neckline
    • Strappy open back
    • Side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5654

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Ready Tropical Knit Wide-Leg Pants

    These alluring tropical wide-leg pants will have you ready for a dreamy vacay! The stretchy knit fabric features a bold abstract tropical print pattern to catch all the glances on your getaway. The pants are shaped with a high-rise elasticized waistband for comfortable wear and a relaxed wide-leg silhouette for a trendy look. Style with the matching crop top and hoop earrings.

    Shop Matching Top: Vacay Ready Tropical Knit Halter Crop Top

    Fit & Features

    • Abstract tropical print
    • Stretchy knit
    • High elasticized waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2481

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Meet For Golden Hour Tie-Front Top

    The top that turns sunsets into photo shoots. Designed with long flowy sleeves and a flirty tie-front, it's made for vacays, day dates, and spontaneous weekend plans.

    Fit & Features

    • Airy linen-blend woven fabric
    • Long bell sleeves
    • Tie-front closure
    • Fitted ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-000012

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boho Cutie Crochet Wide-Leg Pants

    Show off the cutest boho vibe in these breezy crochet wide-leg pants! Designed with an airy sheer crochet knit fabric, these pants are perfect for summer days spent by the coast. They feature a high waist, a hip-hugging fit, and a wide-leg silhouette for that effortlessly chic vibe. Complete your look with the matching crop top and a pair of strappy sandals!

    Shop Matching Top: Boho Cutie Bell Sleeve Crochet Crop Top

    Fit & Features

    • Sheer crochet knit fabric, moderate stretch
    • High-rise elastic banded waist
    • Hip-hugging fit
    • Wide-leg silhouette
    • Panty lining not included
    • Runs true to size

    Style Number/Barcode: 06502-2488

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Much Love Sweetheart Swiss Dot Mesh Mini Dress

    It's too easy to fall for this flirty swiss dot mesh mini dress perfect for soirees! The sweetheart neckline and padded bra cups provide a flattering fit, while the adjustable spaghetti straps and dual front ruched drawstrings allow for a customizable look. The bodycon fit and mini-length hem showcase your figure, all in a beautiful swiss dot mesh fabric. Complete the look in sandals.

    Fit & Features

    • Swiss dot mesh fabric, sewn-in knit lining, stretchy
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Padded bra cups
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3253

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Dreams Hanky Hem Floral Mini Dress

    Sweet and dreamy will be your vibe in this adorable floral mini dress! Designed with a stretchy sheer mesh fabric with a knit lining for coverage, the short dress showcases a blooming floral print for the prettiest look. It features a sleeveless V-neckline with dainty lace trim for a feminine touch, spaghetti straps, a trendy drop waist silhouette, and a mini-length asymmetric hanky hem with a flowy A-line fit. Style with bow hair pins and strappy mules.

    Fit & Features

    • Floral print
    • Stretchy sheer mesh fabric with knit lining
    • V-neckline with lace trim
    • Spaghetti straps
    • Drop waist silhouette
    • Asymmetric hanky hem, A-line fit
    • Runs true to size

    Style Number/Barcode: 05101-3462

    Category Name: Vacation Looks

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Express Your Style V-Neck Ruffle Bodycon Mini Dress

    Express your devotion to style in this charming sleeveless mini dress perfect for casual showers or brunch! This dress features adjustable spaghetti straps for the perfect fit, a flirty V-neckline with a bust tie for added charm, and a bodycon fit to accentuate your curves. The mini-length hem and ruffle trim throughout add a touch of romance to this head-turning dress. Complete the look with earrings.

    Fit & Features

    • Ruffle trim throughout, knit fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • V-neckline with bust tie
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5789

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Serenity V-Neck Crochet Crop Top

    Flirty yet casual, this crochet crop top is perfect for grabbing cocktails at sunset by the beach! The delicate v-neckline and shoulder straps give a flattering silhouette, while the cropped hem adds a cute touch. Complete the look in a flowy maxi skirt and sandals.

    Fit & Features

    • Sheer crochet fabric, no stretch
    • V-neckline
    • Shoulder straps
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06005-2015

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetie Status Halter Crochet Trim Babydoll Dress

    You'll look absolutely adorable in this babydoll dress at showers, birthdays, or backyard parties! The halter neckline and cutout bodice add a touch of allure, while the crochet trim and babydoll silhouette create a delicate and feminine look along the short-length hem. Complete the look in sandals and hoop earrings.

    Fit & Features

    • Gauze woven fabric, woven lining, no stretch
    • Halter neckline with spaghetti strap ties
    • Cutout bodice
    • Crochet trim
    • Babydoll silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5421

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • About A Girl Bow Canvas Tote Bag

    Carry your essentials in style with this charming bow canvas tote bag. Perfect for shopping trips, beach days, or casual outings, this adorable tote adds a cute touch to any outfit.

    Fit & Features

    • Bow print design
    • Top handles
    • Spacious interior
    • Canvas material

    Style Number/Barcode: 07203-000032

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Profound Bloom Off-The-Shoulder Floral Skater Dress

    You'll be blossoming from all the compliments you'll get wearing this off-the-shoulder floral dress! This skater dress features a playful sweetheart neckline, a bust tie, and a ruffled short-length hem bringing plenty of sass and sweetness to your style. Complete the look with earrings and strappy sandals for any occasion!

    Fit & Features

    • Floral print, woven fabric, bust lining
    • Off-the-shoulder, sweetheart neckline
    • Padded bra cups, back zipper and hook-eye closure
    • Skater silhouette
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3459

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Escape Tropical Print Palazzo Pants

    Escape to your dream vacay in these tropical print palazzo pants offering a high-rise waist and a flowy, wide-leg silhouette. Style with the matching tie-front top and your fave sandals.

    Shop Matching Top: Sunny Escape Tropical Print Tie-Front Top

    Fit & Features

    • Woven fabric
    • Tropical print
    • High-rise waist, front button and hidden zipper closure
    • Pleating
    • Wide-leg fit
    • Relaxed silhouette
    • Runs true to size

    Style Number/Barcode: 06302-000002

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Icon Basic Thong Sandals

    A picture-perfect sunny day calls for these basic thong sandals to style with your everyday look!

    Fit & Features

    • Almond toe
    • Sleek thong toe strap
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-000003

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free