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.

  • 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 Looks

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fierce And Trendy Mid-Rise Leopard Mini Skort

    Unleash your fierce and trendy side in this leopard mini skort! The belted waist and pleated skirt overlay create a trendy look while the mini hem shows off your legs.

    Fit & Features

    • Leopard print, denim fabric
    • Mid-rise belted waist, belt loop accents
    • Pleated skirt overlay, side zipper closure
    • Shorts lining
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06603-0430

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: LEOPARD

    Available Size: S, M, L

  • 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 Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Pleats High-Rise Chiffon Palazzo Pants

    Pretty pleats make these high-rise palazzo pants a chic find! Style with a crop top and heels for dinner and drinks.

    Fit & Features

    • Chiffon woven fabric, knit lining
    • High-rise waist
    • Wide-leg pleated silhouette
    • Runs true to size

    Style Number/Barcode: 06402-1464

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • In For The Frills Mid-Rise Eyelet Ruffle Shorts

    Romp around in these adorable eyelet ruffle shorts for weekend brunch or a festival! Designed with a smocked mid-rise waist and flirty lace trim.

    Fit & Features

    • Eyelet lace chiffon fabric
    • Stretchy knit shorts lining
    • Smocked mid-rise waist
    • Ruffled silhouette
    • Runs true to size

    Style Number/Barcode: 06403-1110

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: 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 Looks

    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 Looks

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Night Moves Sequin Mini Skirt

    Own the night in this dazzling sequin mini skirt for a chic shimmer!

    Fit & Features

    • Sequin embellished
    • Low-rise waist
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06401-0749

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: M, L

  • 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 Looks

    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 Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mermaid Muse Starfish Chain Belt

    Create a mermaid-core inspired look with this trendy starfish chain belt perf for layering over your summer 'fits.

    Fit & Features

    • Textured metal starfish design
    • Chain-link attachments
    • Back adjustable chain with lobster clasp closure

    Style Number/Barcode: 07301-000031

    Category Name: Vacation Looks

    Price: $16.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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 Looks

    Price: $2.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Little Miss Charming Strappy Back Denim Romper

    Turn heads with your charm in this denim romper at concerts or weekend fun! Designed with a strappy open back, side pockets, and a pleated short hem, this romper is both stylish and functional.

    Fit & Features

    • Denim fabric
    • Halter V-neckline, keyhole cutout
    • Strappy open back, zipper closure
    • Side pockets
    • Pleated short hem
    • Runs true to size

    Style Number/Barcode: 06603-000008

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: M

  • Floral Crush Flower Stud Earrings

    Major flower power energy happening here. These flower stud earrings add the perfect flirty touch to your everyday vibe—whether it’s jeans and a tee or your fave dress.

    Fit & Features

    • Dainty metal flower design
    • Center rhinestone embellishment
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000122

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • 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 Looks

    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 Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chicest Look Bangle Bracelet

    Serving sculptural drama in the chicest way. This bangle bracelet levels up your wrist stack with a bold curve that keeps it luxe.

    Fit & Features

    • Metal material
    • Thick bangle silhouette
    • Sculpted dome shape
    • Clasp design

    Style Number/Barcode: 07003-000031

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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 Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute By The Shore Two Pack Seashell Hair Claw Clips

    These ocean-inspired seashell hair claw clips effortlessly secure your locks while adding a touch of beachy elegance to any look.

    Fit & Features

    • Two pack claw clip set
    • Seashell design

    Style Number/Barcode: 07006-000008

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • 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 Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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 Looks

    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 Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beach Siren Energy Crochet Lace Duster

    Sunkissed, styled, and totally that girl—this crochet lace duster brings the heat wherever you go. With a flirty tie-front finished with boho-chic beads and a dreamy longline fit, it's the layer your bikini or outfit has been begging for

    Fit & Features

    • Sheer crochet lace
    • Tie-front with bead detail
    • Bell long sleeves
    • Flowy longline hem
    • Runs true to size

    Style Number/Barcode: 06202-000021

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: TAN

    Available Size: S, M, L, XL

  • 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 Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free