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.

  • Bold Accents Resin Bangle Bracelet

    A bold little accent that does all the talking. This resin bangle brings that polished-but-playful vibe—perfect for stacking or rocking solo.

    Fit & Features

    • Smooth resin material
    • Classic bangle silhouette
    • Solid structured fit
    • Lightweight and comfortable

    Style Number/Barcode: 07003-000112

    Category Name: Vacation Looks

    Price: $11.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: NS

  • Blissfully Cute Three Piece Headband Set

    Add a finishing look to your tresses with this three-piece headband set! The set includes a denim headband with faux pearl embellishments, a chain link metal headband, and a faux pearl headband. Style with an adorable shoulder purse for any event!

    Fit & Features

    • Three-piece headband set
    • One denim headband with faux pearls
    • One chain link metal headband
    • One faux pearl headband

    Style Number/Barcode: 07006-0467

    Category Name: Vacation Looks

    Price: $3.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Moment Bow Block Heels

    These playful floral block heels are giving garden party glam with a cute bow—perfect for twirls, toasts, and turning heads at your next event!

    Fit & Features

    • Block heel
    • Square toe
    • Wide strap with bow
    • Adjustable ankle strap with buckle closure
    • Floral print
    • Faux leather padded insole
    • Runs true to size

    Style Number/Barcode: 07401-000362

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: MULTI

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

  • Smooth Moves PU High-Rise Shorts

    Oh-so-contemporary and sleek, these smooth faux leather shorts feature a high-rise waist, front snap-button, hidden zipper closure, side pockets, seam detailing, and a fitted cheeky hem. The lined faux leather fabric has minimal stretch. Complete the look in a basic tee and boots for an edgy vibe.

    Fit & Features

    • High-rise waist
    • Front snap-button and hidden zipper closure
    • Side pockets
    • Seam detailing
    • Fitted, cheeky hem
    • Faux leather lined fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06403-0241

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L, XS

    Product Badge:
    • Best Seller
  • Silicone Adhesive Lifting Bra

    This lifting sticky bra with adjustable lace-up detail provides the perfect support and lift for any open-back or strapless style. The sticky push-up bra is made of a smooth gel with a skin-like appearance and has an adjustable lace-up design to give you a customizable fit.

    Fit & Features

    • Soft, seamless padding
    • Lined with a strong adhesive to stay in place all day
    • Lace-up system
    • Can be worn up to 25 times

     

    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: 07101-0209

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: A, C, D

  • Elevated And Chic Faux Leather Trench

    Layer on an elevated and chic style with this faux leather trench. The jacket features a lapel collar, long sleeves, side pockets, a tie-front belt to cinch the waist, and a mid-length, relaxed fit. The smooth faux leather fabric has a moderate stretch. Complete the look with heeled booties.

    Fit & Features

    • Lapel collar
    • Long sleeves
    • Side pockets
    • Tie-front belt
    • Mid-length, relaxed fit
    • Lined faux leather fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06204-1062

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tiny & Textured Shimmer Hoops

    These hoop earrings have a hint of shimmer to them and are the perfect detail to complete your look. They feature a dainty textured design that is unique from your typical hoop earrings. A great accessory for girl's night, pair these hoops with a crop top and faux leather mini skirt for an edgy vibe.

    Fit & Features

    • Thin textured design
    • Slight shimmer
    • Hook and loop closure, post-back closure

     

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

    Style Number/Barcode: 07001-0116

    Category Name: Vacation Looks

    Price: $6.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Go To Rhinestone Band Flat Sandals

    Step into these glam rhinestone band flat sandals as your new go-to for casual plans or vacay! Featuring an almond toe and a single band adorned with sparkling rhinestones, these sandals will add a touch of glamour to any outfit. The cushioned faux leather footbed provides all-day comfort. Complete the look in a cute romper.

    Fit & Features

    • Almond toe
    • Rhinestone embellished single band
    • Rhinestone trim, flat sole
    • Luxe fit faux leather cushioned footbed
    • Runs true to size

    Style Number/Barcode: 07404-1160

    Category Name: Vacation Looks

    Price: $12.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Add Some Flair Ruffle Detail Midi Dress

    Add some flirty flair to your look with this gorgeous ruffle detail midi dress! It features a sleeveless square neckline, spaghetti straps that lead to a cross-back strap design, a sultry ruffled front slit to show some leg, and a midi-length, sleek, curve-hugging silhouette. The dress is composed of a crepe fabric that offers a moderate stretch. Style the look with eye-catching strappy heels for the perfect date night outfit.

    Shop Long Crepe Version: Tiffany Sleeveless High Slit Formal Dress

    Shop Satin Midi Version: Ravishing Ruffles High Slit Midi Dress

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Strapless or adhesive bra recommended
    • Cross-back strap design, front slit, ruffled hem
    • Midi-length silhouette
    • Crepe fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-0885

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Currently In Paradise V-Neck Tropical Midi Dress

    This tropical midi dress will be with you paradise for a stylishly chic vacation! Featuring a V-neckline adorned with spaghetti straps and a tie-back design, it's the perfect form-hugging dress for any island adventure. With a side slit and midi-length hem, you'll be sure to turn heads! Complete the look in wedge sandals and earrings.

    Fit & Features

    • Tropical print, stretchy knit fabric, sewn-in knit lining
    • Spaghetti straps
    • V-Neckline
    • Tie-back design
    • Side slit
    • Form-hugging
    • Runs true to size

    Style Number/Barcode: 05102-5633

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cubic Zirconia Teardrop Necklace And Studs

    This sophisticated cubic zirconia necklace and stud earrings set will dazzle up the room. The necklace's dainty chain leads to a center teardrop charm. The pack also comes with gorgeous matching teardrop stud earrings so you can wear them together for a beautiful look. Accessorize with this set for brunch with the girls! Pair with a flirty floral dress and cute wedges.

    Fit & Features

    • Dainty chain with teardrop charm
    • Adjustable lobster clasp closure
    • Cubic zirconia embellishment
    • Matching teardrop stud earrings
    • Post-back closures

     

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

    Style Number/Barcode: 07002-4752

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: SILVER

    Available Size: NS

  • Statement Made High-Rise Dual-Slit Maxi Skirt

    The statement has been made when you step out in this maxi skirt on vacay or at a pool party! The breezy knit skirt boasts a flattering high-rise elasticized waistband, a built-in cheeky lining, dual high front slits to bare some skin, and a flowy maxi-length hem. Complete the look in a flirty tie-front top and sandals.

    Fit & Features

    • Stretchy knit fabric
    • High-rise elasticized waist
    • Built-in cheeky underwear lining
    • Dual high front slits
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-0975

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweetest Thing Strappy Back Halter Babydoll Dress

    Experience the ultimate blend of sweet and sultry in this babydoll mini dress at shower celebrations or backyard parties! The delicate lace trim on the halter V-neckline adds a touch of femininity, while the strappy open back turns heads along the ruffled, flowy silhouette.

    Fit & Features

    • Woven fabric, woven lining
    • Halter V-neckline, lace trim, bust tie
    • Strappy open back, adjustable spaghetti straps
    • Ruffled babydoll silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6036

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sealed With Charm Short A-Line Dress

    Seal your look with this charming A-line dress for a rehearsal dinner or sunset dinner date! The dress features a sleeveless sweetheart neckline, adjustable spaghetti straps, a padded bust, and a flattering short-length hem. Complete the look in chic block heels.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Padded bust
    • A-line silhouette
    • Short-length hem
    • Poplin fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-3152

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE-2

    Available Size: M, L

    Product Badge:
    • Sale
  • Eclectic Charm Teardrop Stone Necklace

    Adorn your look with this eclectic necklace featuring a braided band with a teardrop stone design. Includes a back adjustable chain with a lobster clasp closure. Complete the look in a tropical dress for vacation!

    Fit & Features

    • Braided band
    • Teardrop stone design
    • Back adjustable chain with lobster clasp closure

    Style Number/Barcode: 07002-1788

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The One You Need Mini Dress

    Step out in style with this sexy ribbed knit mini dress, perfect for brunch with your besties or a relaxed weekend outing. Its minimalist bodycon silhouette pairs effortlessly with an oversized denim jacket or a fitted blazer for a look that's polished yet effortlessly chic. The dress's flattering V-neckline is ideal for showcasing delicately layered necklaces, adding a sweet and enchanting touch to your ensemble.

     Fit & Features

    • Sleeveless V-neckline
    • Thin bungee straps
    • Strapless bra recommended
    • Mini-length bodycon silhouette
    • Ribbed knit fabric
    • Figure-hugging fit, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06002-0500

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Parisian Girlie Wool Beret

    Add a pinch of Parisian chic to your wardrobe in this classic beret – ooh la la! Crafted from a soft and luxe wool-blend material with a classic beret design, this hat offers lasting beauty and warmth. Complete the look in a cute faux leather jacket for your next trip to Europe or inspired cafe!

    Fit & Features

    • Classic beret design
    • Wool-blend material
    • Soft and comfortable

    Style Number/Barcode: 07302-1540

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charming Ways V-Neck Floral Crepe A-Line Dress

    All eyes and hearts will be on you in this floral crepe mini dress all season! With puff sleeves and a mini-length hem, this dress is perfect for a playful day out. The A-line silhouette will flatter your figure, making you stand out in style. Complete the look in wedge sandals.

    Fit & Features

    • Floral print, crepe fabric, moderate stretch
    • V-neckline
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5700

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Showstoppin' Staple Long Sleeve Maxi Dress

    Put your curves on display in this basic maxi dress perfect for dressing up or down! The long dress features fitted long sleeves, a classic crew neck, and a flattering bodycon silhouette on hacci rib knit fabric. Complete the look with strappy heels and a purse!

    Fit & Features

    • Hacci rib knit fabric, plenty of stretch
    • Fitted long sleeves
    • Crew neckline
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5331

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunshine Livin' Halter Crochet Crop Top

    This crochet crop top was meant for living under the sun! Whether you're heading to a festival or a getaway, this top will keep you boho-cute. It features a sultry halter neckline with a spaghetti strap tie and an ultra-cropped hem to flaunt your figure. Complete the look with the matching pants.

    Shop Matching Bottoms: Sunshine Livin' High Rise Palazzo Crochet Pants

    Fit & Features

    • Crochet fabric lined with stretchy knit
    • Halter neckline
    • Spaghetti straps
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2492

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Best For Last Halter A-Line Denim Mini Dress

    Be the talk of the town in this flirty denim mini dress perfect for festivals, concerts, or country bars! The plunging halter neckline shows some skin while the flattering A-line silhouette cinches your waist and flows into a flirty flared mini hem.

    Fit & Features

    • Denim fabric, moderate stretch
    • Plunge halter V-neckline, tie straps
    • A-line silhouette
    • Flared mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000070

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glam Rhinestone Square Buckle Belt

    Glam up your look with this rhinestone square buckle belt! It features a black hued faux leather belt embellished with small silver rhinestones and has a rhinestone detailed square buckle. Complete the look in a rhinestone trim denim jacket for extra glitz!

    Fit & Features

    • Faux leather material
    • Small rhinestones
    • Detailed rhinestone square buckle
    • Adjustable fit

    Style Number/Barcode: 07301-1024

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everyday Charmer Basic Rib Knit Maxi Dress

    A basic maxi dress that brings everyday charm! This long rib knit dress features a square neckline, spaghetti straps, and a flattering bodycon silhouette, you'll love this maxi dress for any occasion. Complete the look in a cute crop jacket and your favorite sneakers! 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Maxi-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5522

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Chills Long Sleeve Slit Mini Dress

    Look cute in this mini dress for casual chills with friends or daytime outings! The mini dress features a classic crew neckline, bell long sleeves, a flattering bodycon silhouette, and a flirty front slit along the hem on rib knit fabric. Complete the look with booties and a handbag!

    Fit & Features

    • Bell long sleeves
    • Crew neckline
    • Bodycon silhouette
    • Front slit, mini-length hem
    • Rib knit fabric
    • Minimal stretch
    • Style runs small

    Style Number/Barcode: 05102-5326

    Category Name: Vacation Looks

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free