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.

  • Flawless Vibes V-Neck Cutout Wide-Leg Jumpsuit

    Arrive looking flawless in this wide-leg jumpsuit for dinner and drinks on vacay or a rooftop party! Featuring a flattering V-neckline and spaghetti straps, this jumpsuit also boasts an O-ring bust insert and cutout bodice for a trendy touch leading to the wide-leg silhouette. Complete the look with heels.

    Fit & Features

    • Texture knit fabric, minimal stretch
    • Spaghetti straps
    • V-Neckline, O-ring insert
    • Cutout bodice
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2507

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sensational Match Ruffle Mini Skort

    Make a sensational impression in this ruffled mini skort on vacay or brunch! Pair with the matching top to complete the cute look.

    Shop Matching Top: Sensational Match Tie-Front Ruffle Crop Top

    Fit & Features

    • Smooth stretchy knit fabric
    • Mid-rise waist
    • Tiered ruffled design
    • Mini-length overlay
    • Fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000088

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Weekend Style Striped Knit Halter Crop Top

    This cute striped halter crop top will stylishly elevate your casual weekend 'fits. Made with a stretchy striped ribbed knit fabric, it features a plunging V-neckline with a trendy tie-front design, a halter strap leading to a partially open back, and a cropped hem with a form-hugging fit. Pair with jean shorts and sneakers.

    Fit & Features

    • Stretchy ribbed knit fabric
    • Plunging V-neckline
    • Tie-front
    • Halter strap
    • Cropped
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06002-1870

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • True Devotion Strapless Ruffle Skater Mini Dress

    Express your true devotion to flirty style in this strapless skater dress perfect for strolling a beach city or a brunch! Featuring a flattering strapless neckline with a tie and stretchy elasticized bands for a comfortable, secure fit. The skater silhouette and ruffled mini-length hem add a touch of flirty fun. Complete the look in strappy sandals.

    Fit & Features

    • Cotton woven fabric with non-stretch lining
    • Strapless neckline with tie
    • Skater silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5711

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chasing Butterflies Belly Chain

    Chase this flirty belly chain to adorn your swimsuit or midriff outfit! The belly chain features a trendy layered design with butterfly charms and a ball chain fastened with a lobster clasp closure. Complete the look with a pair of sandals.

    Fit & Features

    • Layered belly chain
    • Butterfly charms
    • Ball chain 
    • Lobster clasp closure

    Style Number/Barcode: 07002-1833

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sparkling Delight Rhinestone Strappy Sandals

    These sparkling sandals bring dazzling delight to any look! They're designed in a rhinestone embellished strappy design and a flat sole for comfort.

    Fit & Features

    • Square toe
    • Rhinestone-embellished strappy design
    • Flat sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-000025

    Category Name: Vacation Looks

    Price: $18.90

    Availability: In Stock

    Available Color: PEWTER

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Cloud Cruisin’ Oval Frame Sunglasses

    These trendy oval sunglasses serve retro realness with a sleek plastic frame—perfect for iced lattes, low-effort fits, and avoiding eye contact with your ex.

    Fit & Features

    • Smooth plastic oval frames
    • Subtle curve with mid-coverage lenses
    • Classic Y2K-inspired silhouette

    Style Number/Barcode: 07008-000049

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: NS

  • Can U Not Crew Neck Crop Tee

    Tell it like it is with this sassy crop tee! It features short sleeves, a crew neck, embroidered "Can U Not" lettering across the front, and a fitted crop hem to flaunt your figure. Complete the look in a mini skirt for extra attitude!

    Fit & Features

    • Stretchy rib knit fabric
    • Crew neckline
    • Embroidered "Can U Not" lettering
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-1835

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Trendsetter Open Weave Tote Bag

    Breezy and on-trend, this tote bag is made with an open weave design for that perfect casual weekend style. It features long dual top handles and a removable woven pouch with a drawstring closure to keep your essentials secure.

    Fit & Features

    • Open weave design
    • Long dual top handles
    • Removable woven pouch, drawstring closure

    Style Number/Barcode: 07203-2119

    Category Name: Vacation Looks

    Price: $24.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Luxe With No Limits Halter Midi Dress

    Quiet luxury, but she still turns heads! With a flattering halter neckline, cutout back, and a sneaky little slit, this midi keeps it classy with just the right amount of edge.

    Fit & Features

    • Pointelle knit fabric
    • Halter neckline, tie straps
    • Cutout back
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000010

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Vacay Muse Tropical Floral Knit Bodycon Mini Dress

    You'll be a gorgeous vacay muse in this tropical floral mini dress! The sleek stretchy knit fabric showcases a blooming tropical floral print perfect for your summer trips. The short dress features a sleeveless square neckline, spaghetti straps, an alluring ruched waist cutout with an adjustable drawstring, and a bodycon silhouette to flaunt your figure. Style with espadrille wedges.

    Fit & Features

    • Tropical floral print
    • Stretchy knit fabric
    • Square neckline
    • Spaghetti straps
    • Ruching waist cutout, drawstring
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5614

    Category Name: Vacation Looks

    Price: $11.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Charm Crochet Seashell Trim Crop Top

    Add the perfect beachy touch with this rib knit crop top! The crew neck adds a modern touch, while the crochet and seashell trim exude a unique coastal vibe. 

    Fit & Features

    • Rib knit stretchy fabric
    • Crew neckline
    • Curved crop hem, crochet and seashell trim
    • Runs true to size

    Style Number/Barcode: 06002-000060

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS/S, M/L

  • She Came to Slay Floral Corset Tube Top

    When your outfit speaks before you do. This abstract floral tube top brings the drama with corset vibes and a flawless, sculpted fit made for rooftop nights and flirty first dates.

    Shop Matching Bottoms: She Came to Slay Floral Maxi Skirt

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Abstract floral print
    • Strapless straight-across neckline
    • Flexible boning
    • Back hook-eye closures
    • Fitted, curved, mid-length hem
    • Runs true to size

    Style Number/Barcode: 06001-000142

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: FUCHSIA

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Set To Amaze Mock Neck Abstract Mini Dress

    Everyone will admire your amazing self in this abstract mini dress all over town! Made with a unique abstract print on airy lined mesh fabric, this dress is sure to turn heads. The sleeveless design and mock neckline add a chic touch, while the ruched side seams, bodycon fit, and mini-length hem show off your curves. Complete the look with earrings.

    Fit & Features

    • Abstract print
    • Sheer mesh fabric with knit lining, plenty of stretch
    • Mock neckline
    • Ruching
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5783

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Snapshot Floral Mesh Mini Skirt

    Get the best pics for the gram in this stunning mesh mini skirt featuring a high-rise waist, short curve-hugging fit, and large floral print pattern.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Large floral print
    • High-rise waist
    • Mini-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-000057

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: S, M, L

  • Out Of Town Strapless Floral Crepe Mini Dress

    The perfect floral crepe mini dress to take with you out of town! Boasting a strapless neckline, this mini-length dress has a trendy contrast foldover design and a bodycon silhouette that flatters your curves. Complete the look in sandals and sunnies!

    Fit & Features

    • Floral print, crepe fabric lined with stretchy knit
    • Contrast foldover design
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3364

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Babe Wide Leg Linen Trouser Pants

    No work and all play are the vibes of these linen trouser pants perfect for casual days out to catching your flight out of town! These must-have linen pants feature a flattering high-rise waist, convenient side pockets to keep your phone or hands warm, and a wide-leg silhouette. Complete the look in the matching cropped vest or corset and sandals.

    Shop Matching Tops:
    Cutest Babe Halter V-Neck Corset Crop Top
    Cutest Babe Strapless Linen Bustier
    Cutest Babe Button Up Linen Vest

    Fit & Features

    • Linen-blend woven fabric
    • High-rise waist
    • Front button and hidden zipper closure
    • Side pockets
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-0811

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweeten Me Up Flutter Sleeve Tie Front Crop Top

    Sweeten your every day in this adorable flutter sleeve crop top on any casual occasion! Featuring playful flutter short sleeves, a trendy tie front design, and a cute ruffled crop hem, this top is perfect for adding a touch of fun to any outfit. Complete the look in jeans and block heels.

    Fit & Features

    • Woven fabric, no stretch
    • Flutter short sleeves
    • Tie front design
    • Ruffled crop hem
    • Runs true to size

    Style Number/Barcode: 06204-1825

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Poolside Flirt Eyelet String Bikini Bottoms

    Sit flirty and pretty in this eyelet string bikini bottom at a pool party or on vacation! Pair with the matching bikini top.

    Fit & Features

    • Eyelet lined fabric
    • Low-rise waist
    • Dual string spaghetti ties
    • Cheeky coverage
    • Runs true to size
    • Returns are not accepted without the hygienic liner

     

    Shop The Matching Bikini Top: Poolside Flirt String Bikini Top

    Style Number/Barcode: 07105-0866

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Get The Look Crochet Halter Crop Top

    Curate effortless vibes in this crochet halter crop top, perfect for pairing with the matching pants for a cute look!

    Fit & Features

    • Embroidered crochet fabric
    • Halter plunge V-neck
    • Crop hem
    • Runs true to size

    Shop The Matching Pants: Get The Look Crochet High-Rise Pants

    Style Number/Barcode: 06003-000036

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Paradise Pick V-Neck Cutout Tropical Maxi Dress

    Enjoy the fun and sun on your paradise vacay in this tropical maxi dress! This flowy maxi silhouette features adjustable spaghetti straps, a flirty V-neckline with a keyhole, and a sultry cutout back. With a front slit, you'll steal the show with every step. Complete the look with sunnies and a straw handbag.

    Fit & Features

    • Tropical print, mesh fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • V-neckline, keyhole
    • Cutout back
    • Front slit
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5692

    Category Name: Vacation Looks

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Points Of Interest Triangle Print Strap Flat Sandals

    Step out in style in these faux leather flat sandals. These sandals feature a round toe and a woven strap with a quirky triangle print, perfect for adding a touch of fun to your outfit while the faux leather flat sole ensures all-day comfort. Complete the look with a trendy handbag.

    Fit & Features

    • Round toe
    • Faux leather flat sole
    • Woven strap with triangle print
    • Runs true to size

    Style Number/Barcode: 07404-1221

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Garden At Sunset Strapless Floral Maxi Dress

    Perfect for RSVPs or cocktail bars at golden hour! This strapless mesh maxi dress hugs in all the right places with a sultry back cutout and dreamy floral print.

    Fit & Features

    • Floral print, mesh-lined fabric, high stretch
    • Strapless neckline
    • Cutout back, lower ruched seam
    • Mermaid silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000338

    Category Name: Vacation Looks

    Price: $48.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Sultry Summer Nights Boho Halter Satin Crop Top

    Sunny days and sultry nights call for this boho satin crop top! The halter neckline and spaghetti strap tie provide a secure and comfortable fit, while the open back and lower tie closure add a touch of daring. With its pointed crop hem, this top is perfect for pairing with your favorite high-waisted bottoms.

    Fit & Features

    • Boho print, satin fabric, stretchy knit lining
    • Halter neckline with spaghetti strap tie
    • Open back with lower tie closure
    • Pointed crop length hem
    • Runs true to size

    Style Number/Barcode: 06003-2558

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale