Vacation Dresses & Outfits
Dive into our stunning lineup of vacation outfits perfect for your getaway. Our collection ranges from trendy, tropical print dresses to breezy cover-ups and vibrant two-piece sets, all designed to tantalize your fashion sense and ignite wanderlust. Uncover an array of beautifully crafted, season-appropriate clothing that effortlessly blends comfort and style, helping you craft those Instagram-worthy looks. Whether you prefer the elegance of beachy maxis or the casual cool of denim shortalls, our collection lets you express your vacation vibes like never before.
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Vacation Outfits & Dresses: Chic Looks for Your Next Getaway
Jet off in style with vacation outfits and vacation dresses designed for every destination. Whether you're soaking up the sun at a beach resort, exploring a tropical paradise, or heading out for a stylish city escape, Windsor has effortlessly chic looks to pack for your next getaway. From breezy crop tops and lightweight skirts to flowy maxi dresses, our collection makes vacation styling easy and fun.
For effortless travel outfits for women, explore trendy bikinis, matching clothing sets, and resort-ready separates that transition seamlessly from day to night. Flowy wide-leg pants, flirty rompers, and breezy sundresses bring casual-cool vibes, while chic club and party dresses ensure you're ready for a night out. Complete your vacay outfits with stylish sandals, statement sunglasses, and woven tote bags for the ultimate getaway look.
Heading to a luxury resort or tropical escape? Maxi dresses in vibrant floral and tropical prints make a statement, while cute women's shorts and lightweight skorts keep your look fresh for sightseeing and strolling along the shore. Whether you're embracing women's resort wear or need versatile summer vacation outfits, Windsor has everything you need to stay stylish from sunrise to sunset.
Shop online, in-app, or visit one of Windsor’s 350+ stores across the U.S. and Canada to find the perfect resort clothing and travel-ready outfits for your next adventure.
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Pair To Perfection Metallic Lace-Up Sneakers
These metallic sneakers pair perfectly with your everyday outfits. They feature a round-toe, a lace-up front closure, and a rubber gum sole.Â
Fit & Features
- Round toe
- Metallic material
- Lace-up front closure
- Rubber gum sole
- Runs true to size
Style Number/Barcode: 07407-0231
Category Name: Vacation Dresses & Outfits
Price: $28.90
Availability: In Stock
Available Color: SILVER
Available Size: 5.5, 6, 6.5, 7, 7.5
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Stole Your Heart Charms Shield Sunglasses
These shield sunglasses will steal your heart! They showcase side heart charms for a trendy vibe, oversized tinted lenses, rubber nose supports, and comfortable arms. Complete the look in a cute jumpsuit.
Fit & Features
- Shield style oversized tinted lenses
- Side heart charms
- Rubber nose supports
- Comfortable arms
Style Number/Barcode: 07008-1093
Category Name: Vacation Dresses & Outfits
Price: $11.90
Availability: Out of Stock
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Adorable Chic Bow Cutout Bodycon Mini Dress
Adorable chic and ready to be seen, this sleeveless mini dress is everything! It features adjustable spaghetti straps for a customizable fit, a sweetheart neckline adorned with a statement bow, and a cutout bust to show a peak of skin along the bodycon silhouette. Complete the look in high heels.
Fit & Features
- Smooth knit fabric lined with knit
- Adjustable spaghetti straps
- Sweetheart neckline with bow
- Cutout bust
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-5697
Category Name: Vacation Dresses & Outfits
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Icing On The Cake V-Neck Lace Skater Dress
The perfect lace skater dress that'll take your day somewhere magical! Perfect for rehearsal dinners, birthdays, or graduation. This dress features a flattering V-neckline, spaghetti straps, and a playful cross-back design. Its skater silhouette and surplice ruffled short-length hem will keep you twirling all day! Complete the look in strappy block heels.
Fit & Features
- Lace fabric lined with stretchy knit
- V-neckline, spaghetti straps
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3667
Category Name: Vacation Dresses & Outfits
Price: $44.90
Availability: In Stock
Available Color: NAVY
Available Size: XS, S
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Strut And Snap Ribbed Knit Midi Dress
Strut it out in a knit midi dress that is perf for every day! Designed with a ribbed knit fabric, this dress offers a form-hugging fit with a moderate stretch. It features a sleeveless square neckline, tank shoulder straps, a high side slit accented with glossy metal buttons, and a midi-length hem. Complete the look with mules.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Ribbed knit fabric with moderate stretch
- Square neckline
- Tank shoulder straps
- Metal button accents
- Side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-1167
Category Name: Vacation Dresses & Outfits
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Raise The Bar Wide-Leg Jumpsuit
Raise the bar and strut in this sleeveless jumpsuit featuring a statement design with a plunge halter neckline and an alluring open back. Complete the look with earrings.
Fit & Features
- Smooth knit fabric, plenty of stretch
- Plunging sleeveless halter neckline
- Halter neck ties
- Open back
- Wide-leg silhouette
- Jumpsuit in size small is 58" shoulder to hem with a 13" front rise and a 30" inseam
- Runs true to size
Style Number/Barcode: 06502-2551
Category Name: Vacation Dresses & Outfits
Price: $46.90
Availability: In Stock
Available Color: RUST, BLACK
Available Size: S, M, L
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Effortless Style Short Sleeve Ribbed Knit Crop Top
This adorable short sleeve crop top will make everyday styling effortless. Made with stretchy double-lined ribbed knit, it features a classic crew neckline, short sleeves, and a fitted cropped hem. The perf basic, pair with straight-leg jeans and sneakers.
Fit & Features
- Stretchy double-lined ribbed knit fabric
- Crew neckline
- Short sleeves
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06002-1859
Category Name: Vacation Dresses & Outfits
Price: $6.97 $19.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: S, L
Product Badge:- Sale
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Just Your Stripe Off-The-Shoulder Crop Top
This striped crop top is just what you're looking for! It's designed on stretchy rib knit fabric with a trendy striped print, an off-the-shoulder neckline to bare some skin, and a flirty cropped hem. Complete the look in denim shorts for casual plans.
Fit & Features
- Striped rib knit stretchy fabric
- Off-the-shoulder neckline
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-1972
Category Name: Vacation Dresses & Outfits
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Example Tie-Front Lace Trim Crop Top
You'll be giving off plenty of sweet and sexy vibes in this crop top! Featuring delicate cap sleeves, a flattering lace trim scoop neckline, and dual tie-front closures, this crop top effortlessly adds a touch of romance to any outfit. Complete the look in denim jeans for any casual plans!
Fit & Features
- Rib knit fabric, moderate stretch
- Cap sleeves
- Lace trim scoop neckline
- Dual tie-front closures
- Cropped length
- Runs true to size
Style Number/Barcode: 06202-0476
Category Name: Vacation Dresses & Outfits
Price: $24.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Confident Cutie Sleeveless V-Neck A-Line Mini Dress
Get ready to feel confident and cute in this basic A-line mini dress perfect for styling up or down! The soft and stretchy rib knit fabric includes a full knit lining for added coverage. This dress is perfect for any occasion with a flattering V-neckline, delicate spaghetti straps, and a stylish A-line silhouette. Complete the look in a chunky choker and sneakers!
Fit & Features
- Soft and stretchy rib knit fabric, full knit lining
- V-neckline
- Spaghetti straps
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5651
Category Name: Vacation Dresses & Outfits
Price: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: L
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One Take V-Neck Ruffle Skater Romper
One take in this skater romper and you'll be so obsessed! Its adjustable spaghetti straps and bust tie enhance the ruffled V-neckline, while the tie-back design provides a flattering silhouette. The ruffled layered short-length hem adds a cute touch. Complete the look with a dainty necklace.
Fit & Features
- Knit fabric, moderate stretch
- Adjustable spaghetti straps
- Ruffle V-neckline
- Tie-back design
- Skater silhouette
- Ruffle layered short-length hem
- Runs true to size
Style Number/Barcode: 06503-1142
Category Name: Vacation Dresses & Outfits
Price: $46.90
Availability: In Stock
Available Color: BLACK, PINK
Available Size: S, M, L, XS
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Instant Fave Faux Suede Platform Sneakers
A pair of faux suede sneakers feature a round toe, rubber gum platform sole that elevates the look, a lace-up front, and a side striped design. Perfect for everyday styling.
Fit & Features
- Faux suede material
- Round toe
- Rubber gum platform sole
- Lace-up front
- Side striped design
- Runs true to size
Style Number/Barcode: 07407-0228
Category Name: Vacation Dresses & Outfits
Price: $30.90
Availability: In Stock
Available Color: BEIGE
Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10
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Dancing Moves High-Rise Side Ruffle Midi Skirt
Dance all night in this midi skirt featuring a flattering high-rise waist, form-hugging silhouette, and a high side slit with a flirty ruffled trim perfect for styling with heels. The smooth knit fabric hugs your curves and offers plenty of stretch.
Fit & Features
- Smooth knit-lined stretchy fabric
- High-rise waist
- High-side slit with ruffle trim
- Form-hugging
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06501-1063
Category Name: Vacation Dresses & Outfits
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feeling Daring Texture Knit Mini Skirt
Feel daringly stylish with this mini skirt! This ultra-trendy skirt features a high-rise waist, a bodycon silhouette, and a flirty mini-length hem on texture knit fabric. Dare to stand out and shop the matching top to complete the look!
Shop Matching Top:Â Feeling Daring Texture Knit Crop Top
Fit & Features
- High-rise waist
- Bodycon silhouette
- Mini-length hem
- Texture knit fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 06501-0999
Category Name: Vacation Dresses & Outfits
Price: $9.97 $19.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: M, L
Product Badge:- Sale
- High-rise waist
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Set For Good Cap Sleeve Slit Texture Crop Top
You'll be set for good in this stylish texture crop top all season! Featuring adorable cap sleeves, a V-neckline, and an adjustable bust drawstring atop a flirty slit along the cropped hem. Complete the look with the matching bottoms.
Shop Matching Bottoms: Set For Good High Rise Texture Mini Skirt
Fit & Features
- Texture sheer fabric, bust lining, minimal stretch
- Cap sleeves
- V-neckline
- Adjustable bust drawstring, center slit
- Cropped length
- Runs true to size
Style Number/Barcode: 06001-5287
Category Name: Vacation Dresses & Outfits
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Cowgirl Colored Stone Straw Western Hat
Top off your cowgirl core look with this straw western hat at bachelorettes, festivals, or country bar nights! Made from distressed straw material for a rustic feel. Featuring a string tie bow adorned with a colorful stone and metal ball trim, this hat adds a touch of glam to the classic curved wide brim. Complete the look in cowboy boots.
Fit & Features
- String tie bow, colored stone and metal ball trim
- Classic curved wide brim
- Distressed straw material
Style Number/Barcode: 07302-1604
Category Name: Vacation Dresses & Outfits
Price: $4.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Breezy Boho Sheer Lace Asymmetric Maxi Skirt
Channel an effortless boho vibe in this breezy sheer lace maxi skirt featuring a high-rise waist, ruched detailing with an adjustable drawstring, a high-cut side slit, and an asymmetric hem with a flowy silhouette. Perfect for pairing with a crop top and booties.
Fit & Features
- Sheer lace fabric with mini-length knit lining, plenty of stretch
- High-rise waist
- Ruching, adjustable drawstring
- High side slit
- Asymmetric maxi-length hem
- Flowy fit
- Runs true to size
Style Number/Barcode: 06501-1065
Category Name: Vacation Dresses & Outfits
Price: $39.90
Availability: In Stock
Available Color: IVORY, BLACK
Available Size: XS, S, M, L
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Chic Beauty Strappy Back Knit Midi Dress
This chic sleeveless midi dress is designed with a jacquard patterned sweater knit fabric and features a square neckline, halter spaghetti straps, and a bold open back with cross-back straps and tie-back straps. The midi-length form-hugging silhouette is detailed with a high front slit.
Fit & Features
- Knit fabric with jacquard pattern, moderate stretch
- Square neckline, halter spaghetti straps
- Open back, cross-back straps, tie-back straps
- Contrast seam design at the bodice
- High front slit
- Midi-length form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-2227
Category Name: Vacation Dresses & Outfits
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sporty Luxe Corduroy Baseball Cap
Fit & Features
- Corduroy materialÂ
- Wide brim
- Baseball cap design
- Adjustable back strap
Style Number/Barcode: 07302-1737
Category Name: Vacation Dresses & Outfits
Price: $6.97 $14.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: NS
Product Badge:- Sale
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Cutest Vision Chain Link Trim Sunglasses
Any on-trend, sunny day look isn't complete without these sunglasses! They feature angular square-tinted lenses, rubber nose supports, and chain-link accent arms. Complete the look in sandals.
Fit & Features
- Angular square-tinted lenses
- Rubber nose supports
- Chain-link accent arms
Style Number/Barcode: 07008-1094
Category Name: Vacation Dresses & Outfits
Price: $10.90
Availability: Out of Stock
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Confident Moves Crew Neck Ruffled Mini Dress
Get ready to make confident moves in this sleeveless mini dress perfect for office days and after work play! Featuring a crew neckline and bodycon fit, this dress will have you feeling fabulous. The tiered ruffled mini-length hem adds a playful touch that will have heads turning. Complete the look in stiletto pumps and a blazer.
Fit & Features
- Smooth double-lined knit fabric, moderate stretch
- Crew neck
- Bodycon fit
- Tiered ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5792
Category Name: Vacation Dresses & Outfits
Price: $36.90
Availability: Out of Stock
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Charming Sweetness V-Neck Lace Trim Floral Crop Top
Unlock a charming sweetness in this floral crop top to dress up your everyday look! With delicate spaghetti straps and a lace trim V-neckline, it exudes a romantic appeal with a tiered ruffled silhouette and cropped hem. Complete the look in shorts and strappy sandals.Â
Fit & Features
- Floral print, mesh fabric, bust knit lining
- Spagehtti straps
- Lace trim V-neckline
- Tiered ruffled silhouette
- Runs true to size
Style Number/Barcode: 06001-5389
Category Name: Vacation Dresses & Outfits
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
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Fresh Summer Vibes Wrap-Front Romper
Show off a fresh summer vibe in this elevated and chic woven romper. It features a sleeveless V-neckline, tank shoulder straps that lead to an open back with a cross-back lace-up design, a lower back cutout, a flattering high waist seam, a ruched wrap-front design with a short skirt overlay, and fitted shorts. Style with espadrille wedges for a cute daytime party look.
Fit & Features
- Sleeveless V-neckline
- Tank shoulder straps
- Open back, cross-back lace-up design, tie closure
- Lower back cutout, zipper and hook-eye closure
- High waist seam, ruched wrap-front, short skirt overlay, fitted shorts
- Lined smooth woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0407
Category Name: Vacation Dresses & Outfits
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: M
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Flirty Does It Square Neck Rib Knit Bodysuit
You do flirty well in this rib knit bodysuit perfect for styling with your favorite high-waisted bottoms! Featuring a sleeveless square neckline with a V-wire notch and wide shoulder straps, it hugs your figure with a form-hugging fit. The thong bottom has convenient snap-button closures. Complete the look in best-selling bottoms and heels.
Fit & Features
- Rib knit stretchy fabric
- Square neckline with V-wire notch
- Wide shoulder straps
- Form-hugging fit
- Thong bottom, snap-button closures
- Runs true to size
Style Number/Barcode: 06002-1814
Category Name: Vacation Dresses & Outfits
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale