Vacation Looks
Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.
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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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Bejeweled Glitter Jelly Sandals
You fancy huh! Radiate glam in these glitter jelly sandals featuring a round toe, bejeweled t-strap, and adjustable buckle closure. Complete the look in a day dress for a birthday lunch.
Fit & Features
- Round toe
- Bejeweled t-strap
- Adjustable buckle closure
- Glitter jelly material
Style Number/Barcode: 07404-0969
Category Name: Vacation Looks
Price: $9.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Staple Sheer Button-Up Tunic
This sheer button-up tunic is such a staple for layering over a cute bikini or a lacey bralette! It features long sleeves with button cuffs, a collared neckline, high side slits along a flowy, round hem. Composed of sheer gauze woven fabric with no stretch.
Fit & Features
- Long sleeves, button cuffs
- Collared neckline
- Button-up front closures
- High-side slits
- Flowy round hem
- Sheer gauze woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1649
Category Name: Vacation Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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
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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
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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: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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
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Pretty Blooms Floral Strapless Jumpsuit
Soft, flowy, and effortlessly pretty—this strapless jumpsuit feels like your fave playlist on repeat. Wide-leg fit keeps it relaxed while the floral moment brings the charm to your vacay or weekend plans!
Fit & Features
- Floral print, soft and smooth knit fabric, moderate stretch
- Strapless neckline
- Fitted bodice
- Flowy wide-leg fit
- Runs true to size
Style Number/Barcode: 06502-000038
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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
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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
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Untamed Allure Animal Print Cutout Maxi Dress
For the nights you want all eyes on you. This sultry animal print cutout maxi dress hugs every curve and serves bold, untamed allure to keep you as the main focus.
Fit & Features
- Sheer mesh fabric with mini-length brushed knit lining, high stretch
- Animal print
- Sleeveless plunging halter neckline
- Open back and sides, beaded accents, tie-back straps
- Maxi-length hem, high-cut side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000278
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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
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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
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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
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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
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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
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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
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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
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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
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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: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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
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Coastal Crush Striped Crochet Tie-Front Crop Top
Made for sandy toes and sun-kissed selfies. This striped crochet crop top is your go-to for beach days, boat days, and flirty getaways—just add SPF and salty waves.
Fit & Features
- Crochet fabric, striped pattern
- Plunging V-neckline
- Tie-front design
- Long bell sleeves
- Ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06204-000019
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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
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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
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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
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Effortlessly Elevated Strapless Linen-Blend Dress
Effortlessly elevated, this breezy linen-blend dress is such a summer staple. It features a strapless straight-across neckline, a secure back zipper closure, a ruched fitted high waist, hidden side pockets, and a flowy A-line mid-length silhouette for that relaxed casual-chic vibe. Style with espadrille sandals.
Fit & Features
- Linen-blend fabric
- Strapless straight neckline
- Back zipper hook-eye closure
- Ruched high waist
- Side pockets
- A-line fit, mid-length hem
- Runs true to size
Style Number/Barcode: 05102-5823
Category Name: Vacation Looks
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale