Vacation Dresses & Outfits

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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.

  • Picture Perfect V-Neck Smocked A-Line Midi Dress

    You'll be the picture of perfection in this adorable A-line midi dress at showers or birthday brunch! With its flattering V-neckline and stretchy smocked bodice, this dress hugs your body in all the right places. The tie spaghetti straps add a touch of delicacy, while the V-cut waist seam and A-line silhouette create a flattering look along the midi-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Woven fabric lined with non-stretch woven
    • Tie spaghetti straps
    • V-neckline
    • Stretchy smocked bodice
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3560

    Category Name: Vacation Dresses & Outfits

    Price: $11.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Make Hearts Flutter Short Sleeve Cutout Maxi Dress

    You'll instantly be crushing on this maxi dress perfect for weekend dinner parties or vacation! The flutter sleeves and plunging neckline create a playful vibe, while the elasticized waist and side cutouts show a hint of skin along the flowy maxi-length silhouette. Complete the look in strappy sandals.

    Fit & Features

    • Gauze woven fabric, short knit stretchy lining
    • Flutter short sleeves
    • Plunge V-neckline and V-cut back
    • Elasticized strappy waist with side cutouts
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5719

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

  • Living Sleek Square Chain Trim Sunglasses

    Keep your outfit sleek and trendy in these sunglasses perfect for any sunny day! They feature angled square tinted lenses, rubber nose supports, and chain link trim arms for an edgy flair. Complete the look in sandals.

    Fit & Features

    • Angled square tinted lenses
    • Rubber nose supports
    • Chain link trim arms

    Style Number/Barcode: 07008-1091

    Category Name: Vacation Dresses & Outfits

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • To The Sky Boho V-Waist Tie Flare Pants

    A boho-inspired print adds carefree charm to these flare pants perfect for festivals, concerts, or daytime adventures! Made with soft brushed knit fabric, these boho pants will keep you comfortable and stylish all day long. The high-rise V-waist and adjustable scrunch tie create a flattering, hip-hugging fit, while the flared hem adds a touch of playful movement. Complete the look in a cute crop tee and platform shoes.

    Fit & Features

    • Boho print, brushed knit stretchy fabric
    • High-rise V-waist, adjustable scrunch tie
    • Hip-hugging fit
    • Flared hem
    • Runs true to size

    Style Number/Barcode: 06502-2466

    Category Name: Vacation Dresses & Outfits

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Dream Lace-Up Ruffled Maxi Dress

    A dreamy sleeveless maxi dress perfect for styling for beach city days or coastal vacations! The scoop neckline and bust tie accentuate your figure, while adjustable spaghetti straps provide the perfect fit. The lace-up back adds a touch of charm, while the flowy ruffled silhouette and maxi-length hem exude effortless chicness! Complete the look with strappy sandals and sunglasses.

    Fit & Features

    • Woven fabric, short knit stretchy lining
    • Scoop neckline with bust tie
    • Adjustable spaghetti straps
    • Lace-up back
    • Flowy tiered ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5565

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

  • Burst Of Brilliance Coin Dangle Earrings

    You'll brilliantly shine in these earrings featuring a statement coin design with delicate fringe accents. Complete the look with a bracelet for any occasion.

    Fit & Features

    • Coin design
    • Delicate fringe accents
    • Post-back closure, rubber stopper

     

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

    Style Number/Barcode: 07001-2034

    Category Name: Vacation Dresses & Outfits

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Babe Halter V-Neck Corset Crop Top

    You'll be the cutest babe in this room in this sleeveless corset crop top! Featuring a flattering halter V-neckline, supportive underwire bust, and hidden front hook and eye fasteners, with figure-enhancing flexible boning while the cropped hem adds a touch of playfulness. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Cutest Babe Wide Leg Linen Trouser Pants

    Fit & Features

    • Woven fabric, sewn-in knit lining, no stretch
    • Halter V-neckline
    • Underwire bust
    • Hidden front hook and eye fasteners
    • Flexible boning
    • Back zipper and hook-eye closure
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2542

    Category Name: Vacation Dresses & Outfits

    Price: $36.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Summer Dream Paisley Knit Flare Pants

    Radiate dreamy summer energy in these paisley knit flare pants! The stretchy brushed knit fabric showcases a paisley multi-print pattern for those effortless boho-chic vibes. The pants feature a V-cut high waist, a hip-hugging fit, a form-hugging fit throughout the legs, and a flattering flared-hem silhouette. Style with a crochet crop top and sandals.

    Fit & Features

    • Paisley multi-print pattern
    • Stretchy brushed knit fabric
    • V-cut high waist
    • Hip-hugging, form-hugging fit
    • Flared hem
    • Runs true to size

    Style Number/Barcode: 06502-2498

    Category Name: Vacation Dresses & Outfits

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Elevated Glam Rectangle Sunglasses

    Elevate your look in these rectangle sunglasses made with tinted lenses that provide UV protection and built-in nose pads for comfort. Style with a handbag.

    Fit & Features

    • Angled rectangular-shaped design
    • Plastic frame
    • Asymmetric arms
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1115

    Category Name: Vacation Dresses & Outfits

    Price: $9.90

    Availability: Out of Stock

  • Stylish Persona Strapless A-Line Mini Dress

    Turn on the charm in this strapless mini dress out on the town or at a party! The side ruched seam accentuates your curves while the A-line silhouette provides a flattering fit along the playful mini-length hem. Complete the look with heeled sandals.

    Fit & Features

    • Smooth knit fabric, moderate stretch
    • Strapless neckline
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05103-5642

    Category Name: Vacation Dresses & Outfits

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vibe Of Summer High Rise Eyelet Maxi Skirt

    This gorgeous eyelet maxi skirt will bring you the vibe of summer vacations and parties! The high-rise waist flatters your figure while the flowy tiered ruffled silhouette adds a playful touch to the maxi length hem on breezy eyelet fabric. Complete the look with the matching crop top.

    Shop Matching Top: Vibe Of Summer Tie Front Eyelet Crop Top

    Fit & Features

    • Eyelet fabric, stretchy shorts knit lining
    • High-rise waist
    • Flowy tiered ruffled silhouette
    • Maxi length
    • Runs true to size

    Style Number/Barcode: 06503-1181

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mystical Chic Celestial Rhinestone Earrings

    Keep your style looking mystical in these celestial earrings! They feature a top moon post and cascading chain links with star and rhinestone charms. Complete the look with a ring set for any occasion.

    Fit & Features

    • Moon post
    • Cascading chain links
    • Star and rhinestone charms
    • Post-back closure

     

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

    Style Number/Barcode: 07001-2058

    Category Name: Vacation Dresses & Outfits

    Price: $2.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cargo Darling High-Rise Denim Mini Skirt

    Look and feel so darling in utility fashion! This cargo denim mini skirt is a must for getting that cute and edgy feel. It's crafted from a medium-wash denim fabric offering a classic jean fit and feel with no stretch. The high-rise waist and bodycon fit accentuate your curves, while the dual side flap pockets add a touch of functionality along the trendy mini-length hem. Complete the look in a graphic tee and sneakers for casual plans.

    Fit & Features

    • Medium wash denim fabric, no stretch
    • High-rise waist
    • Bodycon fit
    • Dual side flap pockets
    • Front button and hidden zipper closure, two pockets
    • Runs true to size

    Style Number/Barcode: 06601-0208

    Category Name: Vacation Dresses & Outfits

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • New Level Rectangle Sunglasses

    Take your summer looks to a new level with these trendy shades! The sunglasses feature an angled rectangular-shaped design with a plastic frame, asymmetric-style arms, built-in nose pads, and tinted lenses. Pair with chunky hoop earrings.

    Fit & Features

    • Angled rectangular-shaped design
    • Plastic frame
    • Asymmetric arms
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1113

    Category Name: Vacation Dresses & Outfits

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blooming Beauty Floral Print Mesh Maxi Dress

    Let your beauty bloom with a mesh maxi dress that features a sleeveless sweetheart neckline with lace trim, a bodycon-fit silhouette, and a pretty floral print throughout! Complete your date night look with stiletto heels! 

    Fit & Features

    • Sheer mesh fabric with knit lining, plenty of stretch
    • Floral print
    • Sleeveless sweetheart neckline, lace trim
    • Spaghetti straps
    • Bodycon-like fit
    • Long maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3785

    Category Name: Vacation Dresses & Outfits

    Price: $44.90

    Availability: In Stock

    Available Color: RED

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

  • Blossom In Style Mesh Floral Midi Dress

    Watch your style blossom in this mesh floral midi dress perfect for dates to Galentine's and parties! This bodycon midi dress features a flattering square neckline, adjustable spaghetti straps, and ruched side seams for a perfect fit. The midi-length hem and bold floral print on a lightweight mesh fabric add a touch of fresh charm. Complete the look with dainty jewelry and strappy heels.

    Fit & Features

    • Sleeveless square neckline, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Side ruched seams, bodycon silhouette
    • Side slit, midi-length hem
    • Blooming floral print
    • Mesh fabric, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-3090

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Vibes Celestial Charm Necklace

    Bring on all the chic vibes accessorizing your looks with this trendy celestial charm necklace! It features a dainty chain-link design accented with a star charm, a round charm with sparkling rhinestones, and a moon charm with glitzy gemstones. Style with hoop earrings.

    Fit & Features

    • Chain-link design
    • Star charm
    • Round charm with rhinestones
    • Moon charm with gemstones
    • Back adjustable chain with lobster clasp closure

    Style Number/Barcode: 07002-1832

    Category Name: Vacation Dresses & Outfits

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

  • Chic Find Chunky Chain-Link Necklace

    This chunky chain-link necklace is a chic find for your jewelry lineup! It features a trendy oval and round chain-link design with an adjustable lobster clasp closure. Style with sleek hoop earrings.

    Fit & Features

    • Oval and round chain-link design
    • Back adjustable chain with lobster clasp closure

    Style Number/Barcode: 07002-1824

    Category Name: Vacation Dresses & Outfits

    Price: $2.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Vibes Satin Bow Crochet Tote Bag

    A crochet tote bag that features top handles, satin bow decorations, and a spacious interior perfect for carrying your essentials in.

    Fit & Features

    • Crochet material
    • Top handles
    • Satin bow decorations
    • Spacious interior

    Style Number/Barcode: 07203-2069

    Category Name: Vacation Dresses & Outfits

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

  • Adoring Cutie Sleeveless Lace-Up A-Line Mini Dress

    An attention-worthy A-line mini dress that'll have everyone adoring your cuteness! This square neck dress accentuates your curves while the lace-up back adds a touch of playfulness. The A-line silhouette and mini-length hem are perfect for any occasion. Complete the look in wedges and a clutch!

    Fit & Features

    • Smooth knit fabric lined with stretchy knit
    • Spagehtti straps
    • Square neckline
    • Lace-up
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5689

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Lone Star Distressed Straw Cowboy Hat

    A straw cowboy hat features a distressed wide curved brim with rope trim and an adjustable rope to get a snug fit. Style with cowboy boots for a concert.

    Fit & Features

    • Distressed wide curved brim, rope trim
    • Adjustable inside rope
    • Straw material

    Style Number/Barcode: 07302-1703

    Category Name: Vacation Dresses & Outfits

    Price: $2.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Edgy Chain-Link Bracelet

    Upgrade your outfit with this edgy bracelet! This bold bracelet features multiple chain links for a unique and eye-catching look. Style with a strapless jumpsuit for a cute and trendy look!

    Fit & Features

    • Multiple chain-link design
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07003-0562

    Category Name: Vacation Dresses & Outfits

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Deets Stud And Hoop Earrings Set

    You'll obsess over the trendy deets of this stud and hoop earrings set! The multi-pack features six pairs of varying earrings, including circular studs, rhinestone studs, sleek bar studs, classic huggie hoops, bar studs with hanging chain design, and chic cross-front rhinestone hoops. Include post-back closures. Style with a layered charm necklace.

    Fit & Features

    • Six-pack earrings set
    • Circular studs, rhinestone studs, bar studs
    • Huggie hoops
    • Bar studs with hanging chain detail
    • Cross-front rhinestone hoops
    • Omega closure, post-back closures, rubber stoppers

     

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

    Style Number/Barcode: 07001-1974

    Category Name: Vacation Dresses & Outfits

    Price: $10.90

    Availability: Out of Stock

  • Summer Mood Floral Crochet Sandals

    These floral crochet sandals will put you in the mood for cute summer styling! Designed with a synthetic faux leather upper, they feature an open round toe, a wide banded strap with an adorable floral crochet design in bright hues, and a flat sole. The open back offers effortless on-and-off styling. Pair these sandals with a charm necklace and aviator sunglasses!

    Fit & Features

    • Synthetic faux leather upper
    • Open round toe
    • Single banded strap
    • Multi-colored floral crochet design
    • Open back, flat sole
    • On-and-off styling
    • Runs true to size

    Style Number/Barcode: 07404-1184

    Category Name: Vacation Dresses & Outfits

    Price: $20.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free