Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • Weekend Vibes Wide-Leg Palazzo Pants

    These breezy woven palazzo pants will give off those effortless weekend vibes with their relaxed, wide-leg silhouette. Style with the matching tie-front crop top for a chic look.

    Shop Matching Top: Weekend Vibes Tie-Front Crop Top

    Fit & Features

    • Woven fabric
    • High-rise waist
    • Dual front pockets
    • Pleating
    • Flowy wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06402-000004

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: ORANGE, IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Feeling Daring Texture Knit Mini Skirt

    Feel daringly stylish with this mini skirt! This ultra-trendy skirt features a high-rise waist, a bodycon silhouette, and a flirty mini-length hem on texture knit fabric. Dare to stand out and shop the matching top to complete the look!

    Shop Matching Top: Feeling Daring Texture Knit Crop Top

    Fit & Features

    • High-rise waist
    • Bodycon silhouette
    • Mini-length hem
    • Texture knit fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 06501-0949

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Too Cute To Catch Belted Ruffle Skort

    Catch her if you can—she’s booked, busy, and best dressed. This ruffled mini skort brings all the bounce for brunch, day parties, and spontaneous Insta moments.

    Fit & Features

    • Woven fabric
    • High-rise belted waist, belt loop accents
    • Hidden side zipper and hook-eye closure
    • Ruffled skirt overlay, shorts lining
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06403-000025

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

  • Set For Good Cap Sleeve Slit Texture Crop Top

    You'll be set for good in this stylish texture crop top all season! Featuring adorable cap sleeves, a V-neckline, and an adjustable bust drawstring atop a flirty slit along the cropped hem. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Set For Good High Rise Texture Mini Skirt

    Fit & Features

    • Texture sheer fabric, bust lining, minimal stretch
    • Cap sleeves
    • V-neckline
    • Adjustable bust drawstring, center slit
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06001-5287

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Way She Moves Striped Midi Skirt

    This striped midi skirt has entered the girl's vacay chat! Boasting a sexy bodycon silhouette and mid-rise waist, you'll be the hit of the trip. Pair with the matching top to complete the look!

    Shop Matching Top: Way She Moves Striped Bra Top

    Fit & Features

    • Striped print, scalloped trim, stretchy knit fabric
    • Mid-rise waist
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06401-0743

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK/WHITE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Chic Daydream Butterfly Chain Belt

    Soft girl energy? Activated. This butterfly chain belt flutters right into your faves with dreamy layered charms and delicate movement—perfect for cinching your waist with a little fairycore flair.

    Fit & Features

    • Chain-link design
    • Small and large butterfly charm accents
    • Adjustable fit with lobster clasp closure

    Style Number/Barcode: 07301-000144

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • 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

  • Chic Beauty Strappy Back Knit Midi Dress

    This chic sleeveless midi dress is designed with a jacquard patterned sweater knit fabric and features a square neckline, halter spaghetti straps, and a bold open back with cross-back straps and tie-back straps. The midi-length form-hugging silhouette is detailed with a high front slit.

    Fit & Features

    • Knit fabric with jacquard pattern, moderate stretch
    • Square neckline, halter spaghetti straps
    • Open back, cross-back straps, tie-back straps
    • Contrast seam design at the bodice
    • High front slit
    • Midi-length form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-2227

    Category Name: Vacation Looks

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Cutie Faux Pearl Charm Bracelet

    Catch coastal cute vibes with this bracelet! It's stacked with seashells, starfish, and playful charms along with faux pearls made for your next vacay or summer party.

    Fit & Features

    • Seashell, starfish, and various charms
    • Faux pearls
    • Stretchy fit

    Style Number/Barcode: 07003-000086

    Category Name: Vacation Looks

    Price: $7.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: 07006-000060

    Category Name: Vacation Looks

    Price: $7.90

    Availability: In Stock

    Available Color: YELLOW, PINK

    Available Size: NS

  • Bangle Princess Five-Pack Bracelet Set

    Add a chic finishing touch to your look with this five-pack bangle bracelet set. This stunning collection features five uniquely designed bangles that effortlessly stack together or make a statement worn separately.

    Fit & Features

    • Five-pack bangle bracelet set
    • Various styles and designs

    Style Number/Barcode: 07003-000034

    Category Name: Vacation Looks

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everyday Cowgirl Colored Stone Straw Western Hat

    Top off your cowgirl core look with this straw western hat at bachelorettes, festivals, or country bar nights! Made from distressed straw material for a rustic feel.  Featuring a string tie bow adorned with a colorful stone and metal ball trim, this hat adds a touch of glam to the classic curved wide brim. Complete the look in cowboy boots.

    Fit & Features

    • String tie bow, colored stone and metal ball trim
    • Classic curved wide brim
    • Distressed straw material
    • Adjustable inner strings for a snug fit

    Style Number/Barcode: 07302-1787

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: BROWN-2

    Available Size: NS

    Product Badge:
    • Best Seller
  • Cutest Vision Chain Link Trim Sunglasses

    Any on-trend, sunny day look isn't complete without these sunglasses! They feature angular square-tinted lenses, rubber nose supports, and chain-link accent arms. Complete the look in sandals.

    Fit & Features

    • Angular square-tinted lenses
    • Rubber nose supports
    • Chain-link accent arms

    Style Number/Barcode: 07008-1094

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • Flirt Served Tie-Front Crop Top

    Serve flirty without saying a word. This rib knit tie-front top is giving effortlessly hot with a fitted silhouette that’s made for coffee runs, early brunches, and everything in between.

    Fit & Features

    • Stretchy rib knit fabric
    • Short sleeves
    • Tie-front design
    • Ultra cropped fitted hem
    • Runs true to size

    Style Number/Barcode: 06202-000022

    Category Name: Vacation Looks

    Price: $19.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: L

  • 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
  • Tropic Like It’s Hot Wide Leg Cowl Neck Jumpsuit

    This tropical jumpsuit keeps it cool with a strappy open back and wide-leg silhouette perfect for rooftop dates or vacay nights!

    Fit & Features

    • Tropical print, smooth knit stretchy fabric
    • Halter cowl neckline, spaghetti strap tie, bust knit lining
    • Open back with spaghetti strap tie
    • Flowy wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-000029

    Category Name: Vacation Looks

    Price: $54.90

    Availability: In Stock

    Available Color: BLK/WHT

    Available Size: XS, S, M, L

  • 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
  • Kiss the Spotlight Halter Romper

    Flirty, flowy, and low-key iconic. This romper’s deep neckline and twirl-worthy shorts bring main feed energy to your night-out lineup.

    Fit & Features

    • Slinky knit stretchy fabric
    • Halter plunge neckline, tie straps
    • Open back
    • Flowy shorts hem
    • Runs true to size

    Style Number/Barcode: 06503-000079

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: XS, S, M, L

  • Reusable Gel Lift Pasties

    These gel bra pasties create the perfect lift and nipple coverage for a smooth look. The supportive sticky bra design with its adhesive interior gently lifts the breasts and perfectly covers the nipples for a seamless look. Wear these bra pasties underneath an open-back halter top or strapless cocktail dress with a smooth shapewear style for the ultimate flawless ensemble. Wear with a sleeveless top and a cute pair of denim for your next-day date.

    Fit & Features

    • One pair
    • Gel pasties
    • Reusable, can be worn up to 25 times
    • Provide smoothing, lifting, and supporting effects

     

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07101-0272

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: NS

    Product Badge:
    • Best Seller
  • 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
  • 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
  • Casual Staple Ribbed Knit Bandeau Top

    This casual ribbed knit bandeau top is a staple style to have in your closet. Pair with your fave high-rise bottoms or layered under cute tops!

    Fit & Features

    • Stretchy ribbed knit fabric
    • Strapless straight neckline
    • Cropped hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 07109-000001

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: BLACK, WHITE

    Available Size: S/M, M/L