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.

  • Sunny Style Floral Chiffon Tiered Skater Dress

    Show off an adorable style perf for sunny days in this floral chiffon skater dress! The breezy sheer chiffon fabric is detailed with a dainty floral print for the prettiest look and includes a lightweight woven lining for coverage. The short dress features a sleeveless V-neck and back design with tank shoulder straps, a ruched high waist that flows out to a double-tiered skater skirt, and a flirtatious fit-and-flare silhouette. Complete your outfit with espadrille sandals.

    Fit & Features

    • Dainty floral print
    • Sheer chiffon fabric with woven lining, no stretch
    • V-neck and back, tank straps
    • Ruched high waist, back zipper with hook and eye closure
    • Double-tiered skater skirt
    • Fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3029

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Dreams Denim Lace-Up Espadrille Wedges

    Take your beach style to new heights with these denim lace-up espadrille wedges. The closed almond toe offers a stylish touch while the checkered ankle strap and lace-up ties give you a playful look. Style these wedges with a trendy tote bag for a day under the sun!

    Fit & Features

    • 3.5" Wedge espadrille heel
    • Closed almond toe
    • Checkered ankle strap, lace-up ties
    • Denim material
    • Runs true to size

    Style Number/Barcode: 07406-0339

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Drip Retro Aviator Sunglasses

    With retro-inspired frames and luxe metal detailing, these aviator sunglasses give the final touch for pool parties, matcha runs, and paparazzi-level entrances.

    Fit & Features

    • Lightweight metal frame with retro aviator shape
    • Gradient-tinted lenses with UV protection
    • Slim bridge with supportive nose pads

    Style Number/Barcode: 07008-000018

    Category Name: Vacation Looks

    Price: $11.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Summer Approved Ruffled Lace Mini Skort

    This airy sheer lace mini skort is totally summer approved, featuring a tiered ruffled design with a short overlay and hidden fitted knit shorts. Style with the matching tie-front top for a flirty vibe.

    Shop Matching Top: Summer Approved Sheer Lace Tie-Front Top

    Fit & Features

    • Sheer lace fabric, high stretch
    • Mid-rise waist
    • Tiered ruffled design
    • Mini-length overlay
    • Hidden fitted knit shorts
    • Runs true to size

    Style Number/Barcode: 06503-000087

    Category Name: Vacation Looks

    Price: $26.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Winter Breeze Faux Fur Knit Beanie

    Keep warm from that winter breeze in this adorable chunky knit beanie! It features a twisted cable knit pattern, a fold-over design, and an adorable faux fur pom accent. Style with an oversized sweater.

    Fit & Features

    • Twisted cable knit pattern
    • Fold-over design
    • Faux fur pom

    Style Number/Barcode: 07302-1324

    Category Name: Vacation Looks

    Price: $4.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Major Bombshell Asymmetrical Cutout Dress

    Create a head-turning moment with a mini dress that impresses with sultry details! The dress features a sleeveless V-neckline with a criss-cross bodice, spaghetti straps, a cutout at the midriff, and a short length with an asymmetrical hem. The dress is composed of a lined crepe fabric that offers a form-hugging fit with a moderate stretch. Complete the look with rhinestone heels and a quilted clutch.

    Fit & Features

    • Sleeveless V-neckline
    • Criss-cross bodice, spaghetti straps
    • Cutout at midriff
    • Short length
    • Asymmetrical hem 
    • Lined crepe fabric, form-hugging fit, moderate stretch
    • Runs true to size 

    Style Number/Barcode: 05103-4605

    Category Name: Vacation Looks

    Price: $5.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Eyes on You Knit Striped Mini Dress

    Turn heads without even trying. This tube striped dress hugs you just right with a twist-front that brings the drama.

    Fit & Features

    • Striped pattern, stretchy knit fabric
    • Strapless tube sweetheart neckline
    • Twist bust
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000044

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: TAN

    Available Size: XS, S, M, L

  • So Luxe Faux Nubuck Lace-Up Block Heels

    Keep your look so luxe with stylish heels! The heels feature an open back,  lace-up straps, a strap over the toe, an open square toe,  and a thin block heel. The heels are composed of a faux nubuck material. Complete look with a bodysuit and high waist shorts. 

    Fit & Features

    • Open back 
    • Lace-up straps
    • Strap over the toe 
    • Open square toe
    • Thin block heel 
    • Faux nubuck material 

    Style Number/Barcode: 07401-3066

    Category Name: Vacation Looks

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Edgy Sole Lug Knee High Boots

    Turn the edge in these knee-high boots featuring a round toe, lug platform sole, and side zipper closure, composed of faux leather material. Complete the look in a cool moto jacket.

    Fit & Features

    • Round toe
    • Lug platform sole
    • Side zipper closure
    • Knee-high shaft length
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0863

    Category Name: Vacation Looks

    Price: $4.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sea Me Now Rhinestone Starfish Flat Sandals

    Straight from under the sea! Let everyone admire you in these rhinestone starfish flat sandals. Featuring a round toe and t-shaped thong strap with a sparkling rhinestone starfish accent, these sandals are a chic addition to any outfit. The adjustable ankle strap ensures a comfortable fit while the flat sole provides all-day comfort. Complete the look with a crossbody purse.

    Fit & Features

    • Flat sole
    • Round toe
    • Rhinestone embellished starfish decor
    • Adjustable ankle strap, buckle closure
    • Runs true to size

    Style Number/Barcode: 07404-1226

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Impulse Strappy Open Back Crop Top

    Be on your best cutely dressed behavior in this head-turning sleeveless crop top featuring a halter V-neckline with bungee spaghetti strap ties that shape the strappy open back, and a sheer fitted pointed crop hem. Complete the look in denim shorts and sandals for the perfect summer style!

    Fit & Features

    • Sheer knit fabric, bust knit lining, moderate stretch
    • Halter V-neckline, bungee spaghetti strap ties
    • Strappy open back
    • Pointed crop sheer hem
    • Runs true to size

    Style Number/Barcode: 06001-5333

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sandy Shores Tropical Floral Crop Top

    This vibrant tropical floral crop top will transport you to the sandy shores of a tropical paradise. With its stunning print and strapless neckline, this crop top is perfect for any summer occasion. Pair with the matching skirt.

    Fit & Features

    • Tropical floral print, stretchy knit fabric
    • Strapless neckline
    • Fitted crop hem
    • Runs true to size

     

    Shop the Matching Skirt: Sandy Shores Tropical Floral Maxi Skirt

    Style Number/Barcode: 06001-000141

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ready For My Vacay Bikini Top

    You'll be totally ready for a summer vacay in this bright and bold bikini top. It features halter spaghetti straps, a sweetheart neckline with molded cups, a twist-front design, and a slide hook closure at the back. The all-over tropical print will look so stylish with a sheer flowy duster. Complete your poolside outfit with the matching bikini bottoms.

    Shop Matching Bottoms: Ready For My Vacay Bikini Bottoms

    Fit & Features

    • Halter spaghetti straps
    • Sweetheart neckline, molded cups
    • Twist-front design
    • Slide hook closure at the back
    • Tropical print
    • Runs true to size

     

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0487

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Walking Tall Over The Knee Boots

    These over-the-knee boots were made for your daily stylish walks to and from the coffee shop! They feature a round toe, side zipper closure, PU front panel, a back knit panel, a flat sole, and low heel. Complete the look in a trendy crop jacket. 

    Fit & Features

    • Round toe
    • Side zipper closure
    • PU front panel, back knit panel
    • Flat sole
    • Low heel
    • Runs true to size

    Style Number/Barcode: 07402-0839

    Category Name: Vacation Looks

    Price: $4.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Breezy Vibes Lace Mini Skirt

    Show off a breezy chic vibe in this airy lace mini skirt featuring a high-rise waist and a short form-hugging fit. Style with the matching tie-front top for a weekend getaway.

    Shop Matching Top: Breezy Vibes Lace Tie-Front Top

    Fit & Features

    • Sheer lace fabric with lining
    • High-rise waist, eyelet lace trim
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-000004

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Denim Diva Platform Wedges

    You'll be a total denim diva in these trendy wedges! They feature an open almond toe, a frayed detail toe strap, a frayed ankle strap with an adjustable buckle, and a platform wedge heel. Pair these wedges with a casual dress for a brunch ready look.

    Fit & Features

    • Open almond toe
    • Frayed toe strap
    • Frayed ankle strap, adjustable buckle
    • Closed back
    • Platform wedge heel
    • Denim fabric
    • Runs true to size

    Style Number/Barcode: 07406-0249

    Category Name: Vacation Looks

    Price: $13.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Details Faux Leather Platform Booties

    You may want to get a close look to admire the details on these faux leather platform booties! They feature an almond toe, block heel, side knit panels, and zipper closure with an above-the-ankle shaft. Complete your edgy-girl look with a moto jacket!

    Fit & Features

    • Almond toe
    • Block heel
    • Platform sole
    • Side knit panels and zipper closure
    • Above-the-ankle shaft
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1568

    Category Name: Vacation Looks

    Price: $10.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tie The Knot Bow Strap Flat Sandals

    Tie your outfit together in these cute flat sandals showcasing a square toe, a cutout strap with a knot bow, and a comfortable insole. Complete the look with a trendy handbag for any occasion!

    Fit & Features

    • Square toe
    • Knot bow, cutout strap
    • Flat sole
    • Denim and beige are denim material
    • Black is microsuede material
    • Runs true to size

    Style Number/Barcode: 07404-1222

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Bombshell V-Cut Bikini Bottoms

    Beachy bombshell will be your vibe in these V-cut waist bikini bottoms designed with lurex knit fabric for a trendy metallic sheen. Pair with the matching bikini top and sarong for a sun-kissed look!

    Shop Matching Set: Beachy Bombshell Bikini Top, Beachy Bombshell One-Shoulder Bikini Top, Beachy Bombshell Short Sarong

    Fit & Features

    • Lurex knit fabric, metallic sheen
    • V-cut waist
    • Cheeky fit
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-0868

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Plans Button-Down Linen Top

    Cute for casual plans, this relaxed button-down crop top offers a breezy style to your look! Shop the matching shorts.

    Fit & Features

    • Woven linen-blend fabric
    • Collared neckline
    • Button-down front closures
    • Cuffed dolman short sleeves
    • Relaxed cropped-length hem
    • Runs true to size

     

    Shop The Matching Shorts: Casual Plans Mid-Rise Linen Shorts

    Style Number/Barcode: 06003-000002

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: OFF, WHITE

    Available Size: M, L

    Product Badge:
    • Part of a Set
  • First Sight Lug Block Heel Booties

    It's love at first sight when you set your eyes on these faux leather booties featuring an almond toe, block heel, lug sole, side zipper closure, and an ankle-length fit. Complete the look in a cool moto jacket.

    Fit & Features

    • Almond toe
    • Block heel
    • Side zipper closure
    • Lug sole
    • Ankle-length fit
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1609

    Category Name: Vacation Looks

    Price: $8.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artistic Sensation Strapless Abstract Bubble Mini Dress

    Anytime you step out in this artsy abstract strapless mini dress you'll attract all the attention! The strapless neckline highlights your curves, while the A-line silhouette flatters your figure. The fun and flirty bubble short-length hem adds a playful touch to any occasion. Complete the look with hoop earrings.

    Fit & Features

    • Abstract print, poplin woven fabric, sewn-in knit lining
    • Strapless neckline, non-slip grip lining
    • A-line silhouette
    • Bubble short-length hem
    • Runs small and short, recommend sizing up if needed

    Style Number/Barcode: 05101-3450

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Slip Into Something Floral Mesh Maxi Dress

    The dress you “accidentally” wear to steal the spotlight. This floral mesh maxi drapes you in a soft cowl neckline with a low back and curve-hugging fit that’s ready for cocktails at sunset!

    Fit & Features

    • Floral print, mesh fabric, soft and stretchy knit lining
    • Cowl halter neckline with tie straps
    • Low cut back
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000341

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M, L, XL

  • Make It Slay 50/50 Stiletto Boots

    Make every outfit slay with these stiletto boots featuring a sleek pointed toe, side zipper closure, a knee-high shaft length, and a 50/50 faux leather and scuba knit material. Style with a longline coat for a dinner in the city!

    Fit & Features

    • Pointed toe
    • Stiletto heel
    • Side zipper closure
    • Knee-high shaft length
    • 50/50 faux leather, scuba knit material
    • Runs true to size

    Style Number/Barcode: 07402-0802

    Category Name: Vacation Looks

    Price: $4.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance