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.

  • Perfect Flirt Lace-Up Heeled Thong Sandals

    The perfect faux leather sandals for a flirty look with all your sundresses! These exclusive thong sandals showcase a sleek square toe with a thong-style strap, a thin block heel, and thin lace-up straps that let you customize the style. Complete the look with a trendy handbag for any occasion!

    Fit & Features

    • 3.5" Thin block heel
    • Faux leather material
    • Square toe, thong strap
    • Lace-up straps
    • Runs true to size

    Style Number/Barcode: 07401-4810

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Mode Buckle Cutout Slit Maxi Dress

    A must-have maxi dress for any fashion-forward traveler! Featuring a sweetheart neckline with a trendy buckle accent, a sultry cutout bodice, and a high side slit, this dress will hug your curves and make you feel stylish on your vacation.

    Fit & Features

    • Texture knit fabric, smooth knit stretchy lining
    • Sweetheart neckline with buckle accent
    • Spaghetti straps
    • Cutout bodice
    • High side slit
    • Form-hugging fit, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6082

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Set For Vacay Tropical Floral Strapless Midi Dress

    You'll be set for vacay in this strapless knit midi dress featuring a large tropical floral print for a bold allure. The form-hugging silhouette will flaunt your gorgeous curves.

    Fit & Features

    • Sleek knit fabric with full-length knit lining, high stretch
    • Large tropical floral print
    • Strapless straight-across neckline, no-slip strip
    • Midi-length hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6097

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Crush On You Sleeveless V-Neck Skater Dress

    Everyone will end up with a crush on you in this sleeveless skater dress perfect for beach days or backyard parties! This playful dress features adjustable drawstring shoulder straps and a flattering V-neckline and back design. The fitted waist and skater silhouette create a feminine and flirty look along the short-length hem. Complete the look in heeled sandals.

    Fit & Features

    • Gauze woven fabric lined with stretchy knit
    • Adjustable drawstring shoulder straps
    • V-Neckline and back
    • Fitted waist, skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5500

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Trend Crew Neck Bodycon Midi Dress

    A sleeveless midi dress that'll keep you majorly trendy! Perfect for casual plans or vacations, this midi dress is designed with a flattering crew neckline, bodycon silhouette, and front ruched seam, this dress will accentuate your figure. The front slit adds a touch of drama, while the rib knit fabric offers a sewn-in knit lining for extra coverage. Complete the look with chic sandals and sunnies!

    Fit & Features

    • Rib-knit stretchy fabric, sewn-in knit lining
    • Bodycon silhouette
    • Front ruched seam and slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5596

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Finders Keepers V-Neck Tie Midi Dress

    Once you find this sleeveless midi dress you'll want to keep it! Perfect for semi-formal occasions, this midi dress will make you feel chic and effortless. Designed with an adjustable V-neckline with a bust tie, sleek spaghetti straps, and a flattering curve-hugging silhouette that exudes charm. Complete the look with a bolero shrug sweater and strappy stilettos!

    Fit & Features

    • Woven fabric, no stretch
    • Spaghetti straps
    • Adjustable bust tie
    • Curve-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5551

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer-Coded Crochet Halter Mini Dress

    Serve all the summer vibes in this crochet knit mini dress designed with a halter V-neck with a beaded trim on the straps. Style with espadrille wedges for sunset happy hour.

    Fit & Features

    • Sheer crochet knit fabric with knit lining, moderate stretch
    • Sleeveless V-neckline
    • Tie-back halter straps, beaded trim
    • Partially open back
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6114

    Category Name: Vacation Looks

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold Beauty Floral Maxi Dress

    Just as bold as it is beautiful, this maxi dress is designed with a statement floral print on a body-skimming silhouette. It's perfect for your next vacation or weekend plans!

    Fit & Features

    • Floral print, mesh fabric, soft stretchy knit lining
    • Strapless neckline
    • Form-hugging bodice
    • Relaxed maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6118

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High Intentions Sleeveless Knit Mini Dress

    Take your wardrobe to the next level in this little black dress perfect for day or night plans! This mini dress boasts a sleeveless high square neckline and spaghetti straps for a chic and modern look. The bodycon silhouette hugs your curves, while the mini-length hem adds a touch of flirtatiousness. The lightweight knit fabric offers a moderate stretch. Complete the look in a trendy crop jacket, mules, and a purse!

    Fit & Features

    • Knit fabric with moderate stretch
    • High square neckline
    • Spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1881

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Breezy Chic Belted A-Line Maxi Dress

    Breezy chic, this A-line maxi dress is made with an airy gauze woven fabric accented with sheer lace insets. The belted waist leads to a long tiered flowy fit for that effortless vibe.

    Fit & Features

    • Gauze woven fabric with sheer lace insets
    • Strapless sweetheart neckline with ruffled trim
    • Bust cutout with tie-front detail, ruching, underbust seam
    • Faux leather belted waist, gold metal buckle
    • Maxi-length hem
    • Tiered A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6106

    Category Name: Vacation Looks

    Price: $59.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: M, L

  • Feeling Bliss Rib Knit Pajama Pants

    Experience comfort and bliss in these soft pajama pants! Its elasticized drawstring high-rise waist, wide-leg silhouette, and soft rib knit fabric ensure a cute and cozy lounge. Complete the look with the matching pajama top.

    Shop Matching Top: Feeling Bliss Rib Knit Pajama Tank Top

    Fit & Features

    • High-rise elasticized drawstring waist
    • Wide-leg silhouette
    • Soft rib knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 07103-0955

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Thoughts Sleeveless Cutout Crochet Maxi Dress

    Get summer vibes in an instant wearing this crochet maxi dress perfect for vacation or strolling the boardwalk! Featuring a flattering square neckline, spaghetti straps, and a stunning cutout back with an adjustable drawstring insert and a front slit for movement along the maxi-length silhouette. Complete the look with sunglasses and sandals.

    Fit & Features

    • Crochet knit fabric lined with stretchy knit
    • Spaghetti straps
    • Square neckline
    • Cutout back, adjustable drawstring insert
    • Front slit
    • Maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5742

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Blooms Floral Mesh Halter Maxi Dress

    Showcase your beauty in this lined mesh maxi dress accented with a large floral print for a pretty vibe. It features a sleeveless cowl neckline, halter tie-back spaghetti straps with beaded detailing, an open back with lower tie-back straps, and a maxi-length hem with a form-hugging fit to highlight your curves.

    Fit & Features

    • Sheer mesh fabric with knit lining
    • Large floral print pattern
    • Cowl neckline
    • Halter tie-back spaghetti straps, beaded details
    • Open back, lower tie-back spaghetti straps, beaded details
    • Maxi-length hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5988

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Western Moves Sweetheart Denim Skater Mini Dress

    Show off your Western style in this denim skater mini dress for dancing in the desert at festivals or concerts!

    Fit & Features

    • Denim fabric, stretchy knit lining
    • Sweetheart neckline, underwire bust
    • Adjustable spaghetti straps
    • Back zipper closure
    • Bodycon bodice
    • Skater chiffon lace trim mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6018

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunny Sweet Floral A-Line Mini Dress

    Sunny sweet will be your vibe in this cute floral mini dress designed with a strapless neckline, ruching, and a hanky hem A-line silhouette.

    Fit & Features

    • Knit fabric, high stretch
    • Small floral print
    • Strapless straight neckline
    • Ruching
    • Drop waist
    • Mini-length hanky hem, A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000008

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spice Things Up V-Neck Cutout Skater Dress

    Casual gets a sultry upgrade with this short skater dress perfect for showers and birthdays! This flirty skater dress boasts flowy sleeves, a front and back V-neckline, and a cutout bodice for an alluring look. The gauze fabric adds breezy comfort while the skater silhouette and short length keep you on-trend. Complete the look in strappy wedges.

    Fit & Features

    • Gauze woven fabric lined with stretchy knit
    • V-Neckline front and back
    • Cutout bodice, elasticized straps
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5420

    Category Name: Vacation Looks

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: OLIVE

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Confident Moves Crew Neck Ruffled Mini Dress

    Get ready to make confident moves in this sleeveless mini dress perfect for office days and after work play! Featuring a crew neckline and bodycon fit, this dress will have you feeling fabulous. The tiered ruffled mini-length hem adds a playful touch that will have heads turning. Complete the look in stiletto pumps and a blazer.

    Fit & Features

    • Smooth double-lined knit fabric, moderate stretch
    • Crew neck
    • Bodycon fit
    • Tiered ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5792

    Category Name: Vacation Looks

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: M, L

    Product Badge:
    • Sale
  • The Best Yet Sleeveless Crew Neck Slit Maxi Dress

    The best has come with this stylish basic maxi dress perfect for dressing up or down for any occasion! Crafted from a soft knit fabric, you'll adore this sleeveless dress for its comfort and versatility. The crew neckline gives off a classic vibe while the bodycon silhouette flaunts your curves down to the maxi-length hem with a flirty side slit for movement. Complete the look with a jacket, heels, and a crossbody bag!

    Fit & Features

    • Soft knit fabric, short lining, plenty of stretch
    • Sleeveless crew neckline
    • Tank straps
    • Side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5588

    Category Name: Vacation Looks

    Price: $32.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Let's Get Away Open Back Sleeveless Crop Top

    This sleeveless crop top is exactly what you need for a casual vacay or weekend look! Made with double-lined brushed knit fabric, this top is both soft and durable. The square neckline and open-back twist design create a trendy look, while the fitted crop hem provides a flattering silhouette. Complete the look in jean shorts and sandals!

    Fit & Features

    • Double-lined brushed knit stretchy fabric
    • Twist open back design
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-5250

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance Rules Lace-Up Lace Tunic Top

    Get swept off your feet with the romantic allure of this lace tunic top, designed with a pretty lace-up front and flowy silhouette with a cute ruffle trim.

    Fit & Features

    • Sheer lace fabric, bust knit lining
    • V-neckline, adjustable spaghetti straps
    • Lace-up front design
    • Flowy silhouette
    • Ruffled trim, open front slit design
    • Longline hem
    • Runs true to size

    Style Number/Barcode: 06003-000070

    Category Name: Vacation Looks

    Price: $49.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Breezy Weekend Short Sleeve Button Up Denim Romper

    From coffee shops to running errands, you'll live in this sweet denim romper all weekend! With its collar neckline, form-hugging fit, and short-length hem, this short sleeve romper is perfect for any adventure. And with flap pockets and button-up front closures, you can keep stylish. Complete the look with flat sandals and a crossbody bag!

    Fit & Features

    • Denim fabric, minimal stretch
    • Collar neckline
    • Button-up front closures
    • Flap pockets
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-0383

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ready For Anything Puffer Tote Bag

    Versatile and ready for anything, this puffer tote bag keeps your essentials organized and your look on-trend! It's designed with top handles and an adjustable crossbody strap for versatile wear. The top snap-button closure leads to a spacious and lined interior with side pockets to hold your phone or other loose items and a secure zipper pocket perfect for stashing cash or cards. Complete the look in a casual jumpsuit or romper for weekend plans or travel!

    Fit & Features

    • Insulated puffer material
    • Top handles
    • Adjustable crossbody strap
    • Top snap-button closure
    • Spacious interior, lined, three pockets

    Style Number/Barcode: 07203-2003

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Enchanting Charm Butterfly Rhinestone Lariat Necklace

    Add an enchanting charm to your look with this pretty butterfly rhinestone lariat necklace! It features a two-row design with a rhinestone chain layer and a dainty ball chain layer accented with a rhinestone-embellished butterfly charm, a cascading ball chain lariat, and a sleek rhinestone-adorned bar charm. Style with a chic ring set.

    Fit & Features

    • Two-row layered design
    • Rhinestone chain layer
    • Ball chain layer
    • Rhinestone-embellished butterfly charm
    • Ball chain lariat, rhinestone-embellished bar charm
    • Back adjustable chain with lobster clasp closure

    Style Number/Barcode: 07002-1766

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Match Chevron Knit Midi Skirt

    Trend right with this chevron knit midi skirt for weekend fun or vacation! Pair with the matching top to complete the look.

    Fit & Features

    • Chevron pattern, stretchy knit fabric
    • High-rise waist
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Shop The Matching Top: Trendy Match Chevron Knit Tube Top

    Style Number/Barcode: 06501-1136

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • Sale