Vacation Looks
Vacation outfits should feel as effortless as your out-of-office vibe. Think long floral dresses that move with the breeze, easy cover-ups for poolside lounging, and bold two-piece sets that pop in every photo. From beachy maxis that bring instant elegance to denim shorts that nail casual cool, each piece blends comfort with style so you never have to choose between the two. These looks are made for packing light, looking chic, and serving up Instagram-worthy vacation moments.
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Vacation Looks
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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.
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Sittin' Pretty Tiered Chiffon Maxi Skirt
Sit pretty in this chiffon maxi skirt for effortless elegance on vacation or a weekend escape! The high-rise elasticized waist, flowy tiered silhouette, and maxi-length hem create a flattering look on sheer chiffon fabric. Complete the look in a crop top.
Fit & Features
- Sheer chiffon fabric
- High-rise elasticized waist
- Flowy tiered silhouette
- Runs true to size
Style Number/Barcode: 06401-0653
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Alluring Daydream Off-The-Shoulder Crop Top
Be an alluring daydream come to life in this off-the-shoulder crop top to bare some skin on a breezy sunshine day! Made from smooth woven fabric, this top boasts romantic peasant long sleeves and ruffled trim, a front adjustable ruched drawstring that lets you customize the style, and a stretchy smocked back for easy wear. Complete the look in high-rise jeans and sandals for any occasion!
Fit & Features
- Smooth woven fabric
- Off-the-shoulder
- Ruffled trim
- Adjustable ruched drawstring
- Stretchy smocked back
- Runs true to size
Style Number/Barcode: 06003-2437
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Day To Night Charm Lace-Up Ditsy Floral Mini Dress
Be effortlessly charming in this ditsy floral mini dress day to night! This dress features a flattering sweetheart neckline, sleek spaghetti straps, and a mini bow along the bust to accentuate your figure. The open lace-up back and bodycon silhouette add a touch of sexiness, while the ditsy floral print on stretchy ribbed knit fabric keeps you comfortable and looking cute! Complete the look in boots to edge up your allure.
Fit & Features
- Stretchy ribbed knit fabric, knit lining
- Ditsy floral print
- Sweetheart neckline, mini bow detail
- Spaghetti straps
- Open lace-up back
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5650
Category Name: Vacation Looks
Price: $6.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Travel Pal Twist Chain Straw Panama Hat
Make this straw panama hat your new stylish travel pal! Handmade woven straw creates this sunny-day essential featuring a wide brim to help shade, a twisted chain accent band for a luxe allure, and inner adjustable drawstrings to customize the fit. Complete the look in a dreamy vacation outfit to pack with you for a getaway!
Fit & Features
- Handmade woven straw material
- Wide brim
- Twisted chain band
- Inner adjustable drawstrings
Style Number/Barcode: 07302-1560
Category Name: Vacation Looks
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Here To Play Bow Ruffled Ditsy Floral Romper
This ditsy floral romper is here to play up your flirtatious energy at parties and brunch! Short puff sleeves and a sweetheart neckline add a touch of cuteness to the fitted bodice with a playful bow along the back. The flowy layered ruffled short-length hem on woven fabric makes this romper perfect for a day full of fun. Complete the look in strappy thong sandals.
Fit & Features
- Ditsy floral print, woven fabric, partial lining
- Back zipper and hook-eye closure
- Back bow
- Flowy layered ruffled short-length hem
- Runs true to size
Style Number/Barcode: 06403-0430
Category Name: Vacation Looks
Price: $20.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flawless Steps Rhinestone Lace-Up Sandals
Unleash your inner sparkle in these flawless faux leather sandals for day or night! Designed with square toe and rhinestone embellished knotted straps, these sandals add a touch of glamour to any outfit. The sleek metallic faux leather material and lace-up straps provide both style and comfort with their flat sole. Complete the look with rhinestone earrings for extra luxe!
Fit & Features
- Metallic faux leather material
- Square toe
- Rhinestone embellished knotted straps
- Lace-up
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1167
Category Name: Vacation Looks
Price: $4.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Slay Lace-Up Croc Faux Leather Heels
Show off a trendy slay by stepping out in these lace-up heels! Designed with a faux leather material with a sleek croc-embossed pattern, they feature a thin block heel, an open square-shaped toe, an asymmetric thong strap design, and thin lace-up straps for a sultry vibe. Style these heels with a layered necklace.
Fit & Features
- 3.5" Thin block heel
- Faux leather material with croc-embossed pattern
- Open square toe
- Asymmetric thong strap design
- Lace-up straps with tie closure
- Runs true to size
Style Number/Barcode: 07401-4809
Category Name: Vacation Looks
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simply Fab Patent Faux Leather Kitten Heels
Simply fab, these patent faux leather kitten heels will amp up the style factor of your fave 'fits! They feature a chic stiletto heel for comfortable wear, an open square-shaped toe, a multi-row toe strap and asymmetric strap across the foot, and an adjustable ankle and heel strap with a buckle closure for a secure fit. Pair these heels with a mini handbag.
Fit & Features
- 3.5" Stiletto heel
- Patent faux leather upper
- Open square toe
- Multi-row toe strap, multi-row asymmetric foot strap
- Adjustable ankle and heel strap with buckle closure
- Runs true to size
Style Number/Barcode: 07401-4807
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Getaway Vibes Wide-Leg Pinstripe Woven Jumpsuit
Your look will be giving major weekend getaway vibes in this fresh pinstripe woven jumpsuit! The lightweight woven fabric is accented with a subtle pinstripe pattern for a laidback chic style. Create the look of wearing matching separates with this jumpsuit featuring a sleeveless vest top with a V-neckline, halter straps, and a button-down front leading to an angled cropped hem. The partial open back is followed by a smocked design for added stretch. Show off a hint of skin with the small front cutout at the waist. The high-rise pants have a trendy wide-leg silhouette for a relaxed look. Pair this jumpsuit with hoop earrings and strappy sandals.
Fit & Features
- Pinstripe woven fabric
- Vest top with V-neckline, halter straps, button-down front
- Partial open back, lower smocked design
- Angled cropped hem, waist cutout
- Wide-leg pants, high-rise waist, dual pockets
- Hidden front zipper and hook closure, relaxed fit
- Runs true to size
Style Number/Barcode: 06402-1380
Category Name: Vacation Looks
Price: $59.90
Availability: Out of Stock
Product Badge:- Ships Free
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Butterfly Dreams Handbag
Make a dreamy statement with this butterfly handbag perfect for any occasion! Adorned with convenient top handles and a clasp closure, this bag is both functional and beautiful. The spacious interior keeps your essentials close while durable hard shell plastic material gives this butterfly bag structure. Complete the look in stiletto mules!
Fit & Features
- Top handles
- Clasp closure
- Butterfly design
- Spacious interior
- Hard shell plastic material
Style Number/Barcode: 07203-1981
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Attitude Cat-Eye Sunglasses
These cat-eye sunglasses are perfect for flaunting your trendy attitude with your everyday 'fits! They feature a slightly angled cat-eye design with a wide transparent plastic frame and tinted lenses. Style these cool sunnies with chunky hoop earrings!
Fit & Features
- Angled cat-eye design
- Transparent plastic frame
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1057
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Delightful Cutie Corset Lace-Up Floral Midi Dress
If you aim to charm, this cute ditsy floral midi dress will sweep everyone off their feet at parties! Flaunt your femme figure in the sweetheart neckline, ruched underwire bust, and corset trim bodice. The A-line, midi-length silhouette, and front slit add a flattering look while the lace-up back allows for a customizable fit. Complete the look with a dainty necklace and mules.
Fit & Features
- Ditsy floral print
- Woven fabric lined with stretchy knit
- Underwire bust
- Lace-up, side zipper and hook-eye closure
- Front slit
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-2995
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Mood High Slit Floral Knit Maxi Dress
This adorable high slit floral knit maxi dress is a sweet addition to your spring wardrobe! The dainty floral print on the stretchy knit fabric will create an effortlessly chic look for your casual weekend plans. The dress is shaped with a sleeveless V-neckline and spaghetti straps, while the flowy A-line fit on the maxi-length hem will give you that breezy silhouette you love. Style with hoop earrings and strappy mules.
Fit & Features
- Knit fabric with moderate stretch
- Dainty floral print
- Sleeveless V-neckline
- Spaghetti straps
- High front slit
- Flowy A-line fit
- Runs true to size
Style Number/Barcode: 05102-5518
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Beauty Chiffon Burnout Floral Maxi Dress
Showcase your effortless beauty in this dreamy chiffon burnout floral maxi dress! Designed with a sheer chiffon fabric with a pretty burnout floral pattern, this airy maxi dress is perfect for romantic dates. The sleeveless bodice is shaped with a V-neckline and adjustable spaghetti straps that lead to a partially smocked back for added stretch. The button-down front leads to a high center slit for a chic detail on the flowy A-line silhouette. Style this long dress with a dainty charm necklace and stud earrings.
Fit & Features
- Sheer non-stretch chiffon fabric with burnout floral pattern, mini-length knit lining
- Sleeveless V-neckline
- Adjustable spaghetti straps, partially smocked back
- Button-down front, center slit
- Flowy A-line silhouette
- Strapless or sticky bra recommended
- Runs true to size
Style Number/Barcode: 05101-3200
Category Name: Vacation Looks
Price: $7.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Garden Wanderer Corset Floral Linen Mini Dress
Wander the gardens in this romantic floral linen mini dress as a lovely party guest! With its sweetheart neckline that highlights your bust, adjustable spaghetti straps for a custom fit, and padded bust with a bust tie for trendy detail. The flexible boning and form-hugging silhouette enhance your figure, while the watercolor floral print adds a touch of whimsy. Made from linen fabric with a stretchy knit lining, it's comfortable and stylish. Complete the look with a clutch purse, block heels, and earrings for an unforgettable style!
Fit & Features
- Watercolor floral print, linen fabric lined with stretchy knit
- Padded bust
- Flexible boning
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-2993
Category Name: Vacation Looks
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Swing Into The Season Tie-Back Eyelet Skater Dress
Swing into the season in this charming eyelet skater dress perfect for birthday brunch to day dates! The cap sleeves and sweetheart neckline add a touch of romance, while the padded bra cups provide support. The tie-back design and fitted bodice add a playful twist to the skater silhouette and flirty ruffled short-length hem. Complete the look in strappy platform sandals and a purse!
Fit & Features
- Eyelet lace fabric with woven lining
- Padded bra cups
- Tie-back closure
- Skater silhouette
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05101-3121
Category Name: Vacation Looks
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Like Clockwork High-Rise Wide-Leg Trouser Pants
With a coffee in hand and these trouser pants on, your day will go smooth like clockwork! They feature a flattering high-rise waist with pleating, hidden side pockets for keeping your hands warm, and a chic wide-leg silhouette on woven fabric. Complete the look in a faux leather jacket for a sleek style.
Fit & Features
- High-rise waist with pleating
- Hidden front zipper and hook and eye closure
- Hidden side pockets
- Wide-leg silhouette
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06402-1370
Category Name: Vacation Looks
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Patchwork It Belted Denim Mini Dress
Elevate your style with this patchwork denim mini dress! Featuring a flattering square neckline, spaghetti straps, and a bodycon silhouette, this dress will hug your curves in all the right places. The exposed front zipper closure and flap pockets add a modern touch, while the adjustable waist belt cinches your waist for a perfect fit. Complete the look with platform heels for a daytime party!
Fit & Features
- Patchwork design
- Non-stretch denim fabric
- Exposed front zipper closure
- Adjustable waist belt
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5459
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All About You Lace-Up Floral Mesh Mini Dress
Everyone will take notice of you in this floral mesh mini dress at parties and dressy dinners! This floral print dress is designed with a delicate cowl neckline and spaghetti straps to create a flattering silhouette, while the lace-up back adds a flirtiness. The side ruched seams hug your curves for a bodycon fit, while the mini-length hem is perfect for showing off your legs. Complete the look in strappy sandals and a clutch!
Fit & Features
- Floral print, stretchy mesh fabric with sewn-in knit lining
- Spaghetti straps
- Lace-up
- Side ruched seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3262
Category Name: Vacation Looks
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hint Of Chic Cowl Neck Knit Mini Dress
You'll love the hint of chic style this cowl neck mini dress gives your look! The soft knit fabric has a double-lined design for a smooth seamless look with plenty of stretch. The short dress is shaped with a sleeveless cowl neckline and thin tank shoulder straps. The bodycon silhouette will hug your curves along the mini-length hem. Pair with a handbag and clear heels for happy hour.
Fit & Features
- Stretchy double-lined knit fabric
- Sleeveless cowl neckline
- Thin tank shoulder straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5557
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stand Out In Chic Lace-Up Ombre Mini Dress
Stand out in this chic mini dress at parties! The ombre print adds a touch of boldness to your look while the a cowl neckline, spaghetti straps, and lace-up back flatter and turn-heads! The dress is finished with an accentuating bodycon silhouette and a mini-length hem. Complete the look with rectangular earrings and sleek heels.
Fit & Features
- Ombre print
- Smooth knit fabric, partially lined, stretchy
- Lace-up
- Spaghetti straps
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5607
Category Name: Vacation Looks
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Icon Marble Print Mesh Bodycon Mini Dress
Show up looking stunning like the trendy icon you are in this marble print mesh mini dress! The airy lightweight sheer mesh fabric features a trendy neutral marble print to draw all the attention your way. The sleeveless crew neckline and tank shoulder straps shape the bodice of the mini-length dress, while the bodycon silhouette will flaunt your gorgeous curves. Style with lace-up stiletto heels to get drinks with the squad!
Fit & Features
- Stretchy sheer mesh fabric with knit lining
- Marble print
- Sleeveless crew neckline
- Tank straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5563
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Forever Muse Abstract Satin Bandeau Crop Top
Indulge in high-end artsy style in this satin bandeau crop top you need for vacay! The satin fabric and abstract print make a statement, while the non-slip grip lining and padded bra cups ensure a secure fit, and an ultra-cropped hem and stretchy smocked back offer a flattering look. Pair with the matching bottoms and sunglasses for a chic style!
Shop Matching Bottoms: Forever Muse Abstract Satin Wide-Leg Pants
Fit & Features
- Abstract print, satin woven fabric
- Padded bra cups
- Smocked back
- Halter tie straps
- Runs true to size
Style Number/Barcode: 06003-2256
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Forever Muse Abstract Satin Wide-Leg Pants
Indulge in high-end artsy style in these satin wide-leg pants you need for vacay! The satin fabric and abstract print make a statement, while the flattering high waist and wide-leg silhouette offer a breezy look. Pair with the matching top and sunglasses for a chic style!
Shop Matching Top: Forever Muse Abstract Satin Bandeau Crop Top
Fit & Features
- Abstract print, non-stretch satin woven fabric
- High elasticized waist
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06402-1359
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free