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.

  • Stole Your Heart Charms Shield Sunglasses

    These shield sunglasses will steal your heart! They showcase side heart charms for a trendy vibe, oversized tinted lenses, rubber nose supports, and comfortable arms. Complete the look in a cute jumpsuit.

    Fit & Features

    • Shield style oversized tinted lenses
    • Side heart charms
    • Rubber nose supports
    • Comfortable arms

    Style Number/Barcode: 07008-1093

    Category Name: Vacation Looks

    Price: $5.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Adorable Chic Bow Cutout Bodycon Mini Dress

    Adorable chic and ready to be seen, this sleeveless mini dress is everything! It features adjustable spaghetti straps for a customizable fit, a sweetheart neckline adorned with a statement bow, and a cutout bust to show a peak of skin along the bodycon silhouette. Complete the look in high heels.

    Fit & Features

    • Smooth knit fabric lined with knit
    • Adjustable spaghetti straps
    • Sweetheart neckline with bow
    • Cutout bust
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-5697

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Finishing Touch Woven Shoulder Bag

    Put the perfect finishing touch to your look with this woven shoulder bag! With versatile styling options and a secure magnetic closure, you'll adore this bag all spring and summer.

    Fit & Features

    • Top shoulder strap
    • Detachable crossbody strap
    • Front flap with magnetic closure
    • Spacious interior
    • Woven faux leather material

    Style Number/Barcode: 07203-2130

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Style Short Sleeve Ribbed Knit Crop Top

    This adorable short sleeve crop top will make everyday styling effortless. Made with stretchy double-lined ribbed knit, it features a classic crew neckline, short sleeves, and a fitted cropped hem. The perf basic, pair with straight-leg jeans and sneakers.

    Fit & Features

    • Stretchy double-lined ribbed knit fabric
    • Crew neckline
    • Short sleeves
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06002-1859

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Just Your Stripe Off-The-Shoulder Crop Top

    This striped crop top is just what you're looking for! It's designed on stretchy rib knit fabric with a trendy striped print, an off-the-shoulder neckline to bare some skin, and a flirty cropped hem. Complete the look in denim shorts for casual plans.

    Fit & Features

    • Striped rib knit stretchy fabric
    • Off-the-shoulder neckline
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-1972

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dancing Moves High-Rise Side Ruffle Midi Skirt

    Dance all night in this midi skirt featuring a flattering high-rise waist, form-hugging silhouette, and a high side slit with a flirty ruffled trim perfect for styling with heels. The smooth knit fabric hugs your curves and offers plenty of stretch.

    Fit & Features

    • Smooth knit-lined stretchy fabric
    • High-rise waist
    • High-side slit with ruffle trim
    • Form-hugging
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-1063

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • 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
  • Sun-Kissed Moments Tie-Strap Bikini Bottoms

    You'll have sun-kissed moments in these trendy low-rise bikini bottoms featuring tie straps on each side with beaded detailing. Style with the matching bikini top.

    Shop Matching Top: Sun-Kissed Moments Triangle Bikini Top

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Low-rise waist
    • Tie straps on each side, beaded details
    • Cheeky fit
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000009

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: $3.97 $7.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • 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: $4.97 $10.90

    On Sale: Yes

    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: $11.97 $24.90

    On Sale: Yes

    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: $9.97 $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
  • 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
  • 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
  • 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
  • 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