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.

  • Juicy Sweet Fruit Claw Clip Two Pack

    This two pack claw clips are perfect for adding a juicy twist to your everyday look! Featuring a fun and playful strawberry and cherry design, these clips will hold your hair securely while adding a touch of whimsy.

    Fit & Features

    • Two pack claw clip set
    • One strawberry clip
    • One cherry clip

    Style Number/Barcode: 07006-000044

    Category Name: Vacation Looks

    Price: $8.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Giddy Up Girlie Straw Cowboy Hat

    Saddle up your style with this straw cowboy hat! This western-inspired hat delivers country charm while keeping you cool under the sun. Perfect for music festivals, beach days, or creating that social media-worthy outfit.

    Fit & Features

    • String bow tie
    • Wide curved brim
    • Straw material

    Style Number/Barcode: 07302-000010

    Category Name: Vacation Looks

    Price: $24.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charming Sweetness V-Neck Lace Trim Floral Crop Top

    Unlock a charming sweetness in this floral crop top to dress up your everyday look! With delicate spaghetti straps and a lace trim V-neckline, it exudes a romantic appeal with a tiered ruffled silhouette and cropped hem. Complete the look in shorts and strappy sandals. 

    Fit & Features

    • Floral print, mesh fabric, bust knit lining
    • Spagehtti straps
    • Lace trim V-neckline
    • Tiered ruffled silhouette
    • Runs true to size

    Style Number/Barcode: 06001-5389

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cut to the Chase Halter Jumpsuit

    Serving drama in all the right places. This halter jumpsuit brings the heat with a cutout bodice and a breezy wide-leg fit that’s perf for rooftop parties, sunset dates, or vacay nights out.

    Fit & Features

    • Linen-like woven fabric
    • Halter neckline, spaghetti strap ties
    • Cutout bodice with open tie-back
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-000006

    Category Name: Vacation Looks

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fresh Summer Vibes Wrap-Front Romper

    Show off a fresh summer vibe in this elevated and chic woven romper. It features a sleeveless V-neckline, tank shoulder straps that lead to an open back with a cross-back lace-up design, a lower back cutout, a flattering high waist seam, a ruched wrap-front design with a short skirt overlay, and fitted shorts. Style with espadrille wedges for a cute daytime party look.

    Fit & Features

    • Sleeveless V-neckline
    • Tank shoulder straps
    • Open back, cross-back lace-up design, tie closure
    • Lower back cutout, zipper and hook-eye closure
    • High waist seam, ruched wrap-front, short skirt overlay, fitted shorts
    • Lined smooth woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06403-0407

    Category Name: Vacation Looks

    Price: $44.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ring Me Up Strapless Romper

    Built-in beach club energy. This strapless romper brings the heat with a keyhole O-ring detail and a cinched waist that flatters every curve—perfect for hot days, hotter nights, and bottomless brunches.

    Fit & Features

    • Woven fabric, stretchy knit shorts lining
    • Sweetheart strapless neckline, hoop insert, cutout
    • Back zipper and hook-eye closure
    • Fitted cinch bodice
    • Runs true to size

    Style Number/Barcode: 06303-000027

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

  • Flirty Does It Square Neck Rib Knit Bodysuit

    You do flirty well in this rib knit bodysuit perfect for styling with your favorite high-waisted bottoms! Featuring a sleeveless square neckline with a V-wire notch and wide shoulder straps, it hugs your figure with a form-hugging fit. The thong bottom has convenient snap-button closures. Complete the look in best-selling bottoms and heels.

    Fit & Features

    • Rib knit stretchy fabric
    • Square neckline with V-wire notch
    • Wide shoulder straps
    • Form-hugging fit
    • Thong bottom, snap-button closures
    • Runs true to size

    Style Number/Barcode: 06002-1814

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Breeze Linen High Slit Maxi Skirt

    Channel that coastal chic vibe with this breezy linen maxi skirt featuring a tiered design, high-cut side slit, and flowy A-line silhouette.

    Fit & Features

    • Linen-blend fabric
    • High-rise waist
    • Tiered design
    • Thigh-high side slit
    • Flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 06301-000004

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: M

  • Sassy Style Ruched Knit Halter Skater Dress

    Show off your sassy style at weekend outings in this adorable halter skater dress. Made with stretchy smooth knit fabric, it features a sleeveless V-neckline, trendy tie-back halter straps leading to a partially open back, ruched seams at the waist to accentuate your curves, a short double-layered skater skirt for a flirty vibe, and a fit-and-flare silhouette. Complete the look with a charm necklace and strappy mules!

    Fit & Features

    • Stretchy smooth knit, top knit lining
    • V-neckline, tie-back halter straps
    • Partially open back
    • Ruched seams at the waist
    • Double-layered skater skirt
    • Fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5832

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Table For Two Halter Mini Dress

    All eyes on you (and your table for two). With a plunging neckline and curve-hugging silhouette, this halter mini dress was made to steal the spotlight.

    Fit & Features

    • Jersey knit fabric, stretchy knit lining
    • Halter V-neck
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000312

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, L

  • Style Quotient Platform Denim Block Heels

    Amp your style quotient in these sassy denim block heels perfect for any plans! The round toe and platform sole provide an elevated look, while the adjustable ankle strap with buckle closure secures the style. Complete the look in a mini dress and jacket.

    Fit & Features

    • 5" Block heel
    • Round toe
    • Platform sole
    • Contrast straps
    • Adjustable ankle strap, buckle closure
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4724

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Main Feed Moment Denim Mini Skort

    Classic with a modern twist, this denim mini skort brings Y2K vibes in a trending silhouette! Style with a graphic top for any casual plans.

    Fit & Features

    • Medium wash non-stretch denim, knit shorts lining
    • Mid-rise waist
    • Seam front detailing, form-hugging fit
    • Mini-length hem
    • Front button tab and hidden zipper closure
    • Three-pocket styling, belt loop accents
    • Runs true to size

    Style Number/Barcode: 06603-000025

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: MED, DENIM

    Available Size: XS, S, M, L

  • Animal Instinct Leopard Oversized Sunglasses

    These trendy sunglasses feature oversized square frames with a fierce leopard pattern. Perfect for everyday styling.

    Fit & Features

    • Oversized square frame
    • Leopard pattern
    • 100% UV protection
    • Tinted lenses

    Style Number/Barcode: 07008-1109

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: S

  • Living By The Sea Canvas Tote Bag

    Escape to the beach with this tote bag, featuring charming seashell and starfish prints that capture coastal beauty and a spacious interior perfect for any essentials.

    Fit & Features

    • Top handles
    • Seashell and starfish print design
    • Spacious interior
    • Canvas material

    Style Number/Barcode: 07203-000027

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Coastal Cowgirl Shell Trim Straw Cowboy Hat

    A straw cowboy hat perfect for a day at the beach or festival. This hat features a wide brim to help shade, a string trim with shell and stone decoration, and adjustable inner strings for a snug fit.

    Fit & Features

    • Straw material
    • Wide brim
    • String trim with shells and stone decoration
    • Adjustable inner strings

    Style Number/Barcode: 07302-1643

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Muse Floral Eyelet Chiffon Romper

    You'll be a total sunny muse in this adorable romper made with airy eyelet chiffon fabric and a dainty floral print pattern. The sweetheart neck features a lace-up bust design, leading to the cutest fit-and-flare silhouette with flowy shorts.

    Fit & Features

    • Sheer eyelet chiffon fabric with floral print, stretchy knit lining
    • Sleeveless sweetheart neckline, lace-up bust, padded bra cups
    • Adjustable spaghetti straps
    • Smocked back, zipper hook-eye closure
    • High-rise seam
    • Flowy shorts, fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 06403-000008

    Category Name: Vacation Looks

    Price: $20.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Born To Be Coveted Mid-Rise Lace-Up Denim Skort

    A coveted summer style starts with this mid-rise denim skort perfect for casual plans! Made from denim fabric, this skort is perfect for showing off your legs in a flirty mini-length hem. Its mid-rise waist and form-hugging fit will accentuate your curves, while the playful skirt overlay with lace-up detailing and a slit adds a touch of edginess. Complete the look in a flirty crop top and sneakers.

    Fit & Features

    • Denim medium wash fabric, no stretch
    • Mid-rise waist
    • Back zipper hook-eye closure
    • Lace-up, slit accent
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-0379

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: Out of Stock

    Product Badge:
    • Ships Free
  • Golden Hour Seashell Sandals

    Vacay vibes in every step. These shell-accented sandals are your new go-to for beach walks, brunch looks, and everything in between—comfy, cute, and made for your golden hour moments.

    Fit & Features

    • Faux leather material
    • Open square-shaped toe
    • Thong strap design
    • Metal shell accent
    • Open back, on-and-off styling
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-000020

    Category Name: Vacation Looks

    Price: $16.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Mermaid Mood Starfish and Seashell Earrings

    Giving vacation vibes, even if you’re just at brunch. These earrings mix starfish, seashells, and faux pearls for a playful, ocean-inspired finish.

    Fit & Features

    • Starfish and seashell designs
    • Faux pearl embellishments
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000125

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • City Of Love V-Neck Ruffle Babydoll Dress

    Grab your baguette, passport, and this babydoll dress cause the city of love is calling your name! The playful ruffled shoulder straps and convenient side pockets add a touch of whimsy to this flirty dress. The babydoll silhouette and ruffled tiered hem make it perfect to sweep through Paris looking adorable! Complete the look in strappy sandals and a purse.

    Fit & Features

    • Woven fabric
    • Ruffled shoulder straps
    • Side pockets
    • Babydoll silhouette
    • Ruffled tiered short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5423

    Category Name: Vacation Looks

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Era Multi-Beaded Bracelet Set

    Effortless and made for your boho era. This four-pack bracelet set levels up any look with a mix of bold beads and breezy vibes—just stack and go, babe.

    Fit & Features

    • Four-pack bracelet set
    • Multi-beaded designs with smooth and faceted textures
    • Layered look with mixed bead shapes and finishes
    • Stretchy fit

    Style Number/Barcode: 07003-000027

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Tropical Blooms Flower Hair Claw Clip

    Vacay mode activated! Show off these tropical flower hair claw clips while on your getaway or a chic pool party.

    Fit & Features

    • Tropical flower
    • Claw clip closure

    Style Number/Barcode: 07006-000058

    Category Name: Vacation Looks

    Price: $7.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free