Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

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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.

  • Aesthetic Pairing Three-Pack Bracelet Set

    Elevate any look with this three-pack bracelet set featuring a paperclip chain-link bracelet and two stretchy beaded bracelets. Complete the look with a cute crossbody bag for any occasion!

    Fit & Features

    • Three-pack bracelet set
    • One paperclip chain-link bracelet, adjustable lobster clasp closure
    • Two stretchy beaded bracelets

    Style Number/Barcode: 07003-0561

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Fit Strapless Faux Wrap-Front Romper

    This strapless romper will give you a chic fit with its faux wrap-front design and form-hugging silhouette. Style for happy hour with strappy mules.

    Fit & Features

    • Smooth woven fabric, partial knit lining, moderate stretch
    • Strapless straight neckline, no-slip strip, dart seams
    • Back zipper with hook-eye closure
    • High waist seam
    • Faux wrap-front mini-length overlay, short slit, fitted shorts
    • Romper in size small is 22" top hem to bottom hem with a 12" front rise and a 2" inseam
    • Runs true to size

    Style Number/Barcode: 06403-1105

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Catch Attention Cowl Neck Abstract Floral Maxi Dress

    Catch everyone's attention in this abstract floral maxi dress at cocktail hour! The cowl neckline adds a touch of sophistication while the adjustable spaghetti straps provide a perfect fit. The form-hugging silhouette flatters your figure and the maxi-length hem offers a chic finish. Complete the look with a clutch and heels.

    Fit & Features

    • Abstract floral print, mesh fabric lined with stretchy knit
    • Cowl neckline
    • Adjustable spaghetti straps
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05101-3323

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fluttering Elegance Rhinestone Butterfly Earrings

    These charming earrings add a whimsical style to your look! They feature butterflies with mini rhinestone embellishments, linear chains with bar trim, and a post-back closure. Complete the look with a trendy denim jacket.

    Fit & Features

    • Butterflies with mini rhinestone embellishments
    • Linear chains with bar trim
    • Post-back closure

     

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

    Style Number/Barcode: 07001-2057

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Botanic Chic Textured Leaf Earrings

    These gorgeous earrings feature a textured leaf design that gives your look a nature-meets-luxury allure—perfect for date nights or rooftop brunches!

    Fit & Features

    • Textured leaf design
    • Linear silhouette
    • Fish hook

     

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

    Style Number/Barcode: 07001-000124

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Whimsical Appeal Puff Sleeve Chiffon Skater Dress

    Swiss dots add whimsical appeal to this charming chiffon skater dress perfect for birthdays, graduations, or showers! With sheer puff sleeves, a sweetheart neckline, and a tiered ruffled skater silhouette, this dress is both playful and flattering. Its short-length hem adds a touch of flirty charm. Complete the look in mules and a trendy purse!

    Fit & Features

    • Swiss dot chiffon fabric lined with stretchy knit
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-2999

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    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

  • Resort Calling Mesh Tie Front Top

    Booked the trip? This top is already packed. Featuring a tie-front design, long sleeves and a dramatic crop hem, this floral mesh moment is giving vacation muse energy—made for poolside lounges or rooftop cocktails. 

    Shop The Matching Skirt: Resort Calling Mesh Slit Maxi Skirt

    Fit & Features

    • Floral print, partially lined mesh fabric
    • Long sleeves
    • Tie-front closure
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06202-000032

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Sweet Style Bow Detail Polka Dot Mesh Mini Dress

    Show off the sweetest style on summer dates in this bow detail polka dot mini dress! Designed with an airy sheer mesh fabric with a knit lining for coverage, this mini-length dress is accented with an adorable polka dot pattern for the cutest vibe. It features a sleeveless V-neck and back design with a dainty eyelet trim, tank shoulder straps, a mini bow detail at the bust for a sweet touch, tie-back spaghetti straps, and a flirty flowy A-line silhouette. Pair with strappy mules.

    Fit & Features

    • Polka dot printed sheer mesh fabric with knit lining
    • Plenty of stretch
    • V-neck and back, tank shoulder straps
    • Mini bow detail, eyelet trim
    • Tie-back straps
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5828

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Mood Tropical Print Halter Cutout Jumpsuit

    This sultry tropical print jumpsuit will put you in the vacay mood! Designed with sleek knit fabric, it features an alluring cutout below the bust, a high-rise waist with a hip-hugging fit, and a trendy wide-leg silhouette.

    Fit & Features

    • Smooth knit fabric with knit bust lining, high stretch
    • Tropical print
    • Sleeveless scoop neckline, cutout below the bust
    • Tie-back halter spaghetti straps, partially open back
    • High-rise waist, hip-hugging fit
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-000011

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: XS, S, M, L

  • A Little Wild One-Shoulder Zebra Print Maxi Dress

    Your next night out just got a little wild in this sassy zebra print maxi dress perfect for vacation or the weekend! This form-hugging dress features a one-shoulder neckline and spaghetti strap, with a side drawstring cutout to show some skin. The high side slit and maxi-length hem add a flirty touch to this fierce and flattering piece. Complete the look with heeled sandals and earrings.

    Fit & Features

    • Zebra printed knit fabric, plenty of stretch
    • One-shoulder neckline, spaghetti strap
    • Side drawstring cutout
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5821

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sheerly A Good Time Halter Lace Romper

    You're in for a stylishly good time in this sheer lace romper at festivals or concerts! It boasts a sultry open strappy back and a sheer bodice that flaunts your figure.

    Fit & Features

    • Lace fabric
    • Halter V-neckline, spaghetti strap tie
    • Open back, spaghetti strap tie
    • Sheer fitted bodice
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 06503-000048

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK, IVORY

    Available Size: S, M, L

  • Cute Feels Off-The-Shoulder Sweater Mini Dress

    Feel cute in this off-the-shoulder sweater mini dress all year round! The folded off-the-shoulder neckline adds a flirty touch, while the bodycon fit accentuates your curves perfect for a day or night on the town. Complete the look in block heels.

    Fit & Features

    • Sweater knit fabric, moderate stretch
    • Off-the-shoulder neckline
    • Bodycon fit
    • Mini-length
    • Runs true to size

    Style Number/Barcode: 06005-1947

    Category Name: Vacation Looks

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Clear Obsession PVC Flat Sandals

    You'll be obsessed with these flat sandals perfect for styling on rotation! They feature an almond toe, a clear PVC strap, and a flat sole with edge trim on faux leather material. Complete the look with a trendy crossbody purse.

    Fit & Features

    • Almond toe
    • Clear PVC strap
    • Flat sole with edge trim
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1233

    Category Name: Vacation Looks

    Price: $12.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Darling Babe Floral Woven Puff Sleeve Skater Dress

    Create a darling day date look with this floral puff sleeve skater dress! Made with a lightweight woven fabric, it is detailed with a charming dainty floral print for those sweet feminine vibes. The short dress features a V-neckline with a cute tie-front detail, short puff sleeves with a ruffled trim, a high waist seam, and a skater hem with a flirty fit-and-flare silhouette. Style with a dainty charm necklace and heels.

    Fit & Features

    • Dainty floral print
    • Woven fabric
    • V-neckline, tie-front detail
    • Short puff sleeves, ruffled trims
    • Back zipper closure, high waist seam
    • Short skater skirt, fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3466

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Always Strapless Cutout Ruffle Maxi Dress

    Have all eyes on you in this strapless maxi dress boasting a sweetheart twist neckline and a cutout bodice. The smooth knit fabric hugs your curves along the form-hugging silhouette and creates a front center ruffle design. 

    Fit & Features

    • Smooth knit lined fabric, moderate stretch
    • Strapless sweetheart twist neckline
    • Cutout bodice
    • Center front ruffle design
    • Form-hugging, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3601

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In Full Faith Cross Rhinestone Charm Belly Chain

    Perfect for accentuating your waist, this belly chain complements both casual and dressy outfits with subtle shine and meaningful detail. This delicate belly chain features a sparkling cross charm adorned with rhinestones, adding a touch of elegance and faith-inspired beauty to your look. 

    Fit & Features

    • Cross charm
    • Rhinestone charm
    • Layered chain design
    • Lobster clasp closure

    Style Number/Barcode: 07002-000020

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Stylish Destination Straw Tote Bag

    Whether you're heading on vacay or to the beach, this large straw tote bag will keep you stylish for whatever destination! Its spacious, adjustable drawstring interior lining and pockets make it perfect and functional for keeping your things in while the convenient top handles make it easy to carry around. Complete the look in trendy sandals.

    Fit & Features

    • Straw material
    • Spacious, adjustable drawstring lined interior
    • Interior pocket
    • Top handles
    • Large silhouette

    Style Number/Barcode: 07203-2115

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: NS

  • Looking Back Strapless Strappy Mini Dress

    Make everyone look back at you in this sassy rib knit mini dress! Perfect for summer BBQs or pool parties, this dress boasts a flattering strapless neckline and bust cutout, a strappy back design, and a bodycon fit. Complete the look in sandals and sunnies!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Strappy back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5767

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Blooms Floral Ruffle Chiffon Skater Dress

    Let this tropical floral skater dress bloom into your summer lineup! With a sweetheart neckline featuring delicate ruffle trim, adjustable spaghetti straps and padded bra cups, this skater silhouette will flatter your figure. The mini-length hem adds a flirty touch to this tropical floral printed chiffon dress. Complete the look with a crossbody purse and sandals!

    Fit & Features

    • Tropical floral print
    • Chiffon fabric with woven lining, no stretch
    • Sweetheart ruffle trim neckline
    • Padded bra cups
    • Adjustable spaghetti straps
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3204

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Social Butterfly Charm Necklace

    With an etched butterfly charm on a dainty chain, this necklace is a pretty piece for everyday wear. Complete the look with a stackable ring set.

    Fit & Features

    • Etched butterfly charm
    • Dainty chain
    • Lobster clasp closure

    Style Number/Barcode: 07002-1865

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everyday Chic Cutout Sandals

    Bringing effortless energy wherever you go. These chic slide sandals are your no-brainer pick for sun-soaked strolls, coffee runs, and last-minute plans.

    Fit & Features

    • Square toe
    • H-shaped band
    • Flat sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-000038

    Category Name: Vacation Looks

    Price: $19.90

    Availability: In Stock

    Available Color: WHITE

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

  • Prep For Paradise Strapless Tropical Jumpsuit

    Prep yourself for paradise starting with this tropical jumpsuit to pack in your luggage! Made from a smooth knit fabric showcasing a palm tropical print, this jumpsuit features a strapless neckline with side-ruched seams that accentuate, a flattering wide-leg silhouette. Complete the look with sunglasses and sandals!

    Fit & Features

    • Smooth knit fabric, tropical palm print, moderate stretch
    • Strapless neckline
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2520

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Cutie Strappy Faux Leather Sandals

    Give off cutie vibes in these floral strappy faux leather sandals! They feature a round toe, an asymmetric strappy design with adorable flower accents with faux pearl center detailing, an adjustable ankle strap and heel strap, and a flat sole for comfortable wear. Style with a flowy summer dress for a perf summer look.

    Fit & Features

    • Faux leather upper
    • Round toe
    • Asymmetric strappy design
    • Flower design with faux pearl center details
    • Adjustable ankle strap, heel strap
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1213

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale