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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Flirt Mode Ruffle Mini Skort
A little sweet, a little bold—this one knows exactly what it’s doing. The ruffle mini skirt is fitted and flares out with a ruffle detail that keeps it playful from brunch plans to late dinners. Style with the matching tie-front top.
Shop Matching Top: Flirt Mode Ruffle Sleeve Tie-Front Top
Fit & Features
- Sleek knit fabric, high stretch
- High-rise waist, ruched detailing
- Tiered ruffled design
- Mini-length overlay, fitted A-line silhouette
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06503-000282
Category Name: Vacation Looks
Price: $29.90
Availability: Out of Stock
Product Badge:- Ships Free
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Vacation Calling Floral Mesh Poncho
This poncho says beachside drinks, sunset photos, and a dinner with a view. It features an asymmetric neckline and a flowy, relaxed poncho silhouette with a crop length that flaunts your figure. Style with the matching mini skirt.
Shop Matching Bottoms: Vacation Calling Floral Mesh Mini Skirt
Fit & Features
- Mesh knit fabric, tropical floral print, high stretch
- Asymmetrical neckline
- Relaxed poncho silhouette
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06202-000095
Category Name: Vacation Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Buckle Up Belted Studded Denim Mini Skort
Not your basic mini skort—this one comes with attitude. The denim mini skort cinches with a belted accent and flares out with pleated detailing, giving you that effortlessly styled look. Style with the matching tube top.
Shop Matching Top: Buckle Up Denim Belted Tube Top
Fit & Features
- Denim fabric with distressed details
- Mid-rise waist, belted accent
- Drop waist design
- Nailhead-studded detailing
- Mini-length pleated overlay, A-line silhouette
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06603-000184
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: BEIGE
Available Size: S, M, L
Product Badge:- Part of a Set
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Coast Along Espadrille Wedges
Booked the plans just so you could wear these. These strappy espadrille wedges bring that effortless vacation feel with a lifted sole and barely-there straps that add a cute touch to every outfit.
Fit & Features
- Wedge heel
- Square toe
- Strappy design
- Platform espadrille sole
- Adjustable ankle strap with buckle closure
- Faux leather upper
- Runs true to size
Style Number/Barcode: 07406-000060
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: WHITE
Available Size: 10, 11
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Poolside Plans Jelly Kitten Heels
Vacation mood activated. These jelly kitten heels bring a playful throwback feel with clear thong straps and an easy slip-on design made for sunny day dressing!
Fit & Features
- Kitten heel
- Square toe
- Clear PVC thong strap
- Cushioned insole
- Jelly material
- Runs true to size
Style Number/Barcode: 07401-000707
Category Name: Vacation Looks
Price: $24.90
Availability: Out of Stock
Product Badge:- Ships Free
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Serving Attitude Striped Knit Hot Shorts
Serving shape and attitude in one effortless vibe. These striped knit hot shorts hug your body with a soft, stretchy feel made for last-minute plans that somehow turn iconic. Style with the matching halter top.
Shop Matching Top: Serving Attitude Striped Knit Halter Top
Fit & Features
- Striped ribbed knit fabric, high stretch
- Mid-rise waist
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06503-000254
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLUE
Available Size: S
Product Badge:- Part of a Set
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Serving Attitude Striped Knit Halter Top
Serving shape and attitude in one effortless vibe. This striped knit halter top hugs your body with a soft, stretchy feel made for last-minute plans that somehow turn iconic. Style with the matching hot shorts.
Shop Matching Bottoms: Serving Attitude Striped Knit Hot Shorts
Fit & Features
- Striped ribbed knit fabric, high stretch
- Sleeveless V-neckline
- Halter strap
- Partially open back
- Form-hugging fit
- Mid-length hem
- Runs true to size
Style Number/Barcode: 06005-000333
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island Crush Flower Two-Pack Hair Clips
Serving vacation pics even when you’re just running late to brunch. These two-pack flower hair clips add the cutest little pop to messy buns, slick backs, and beach day waves!
Fit & Features
- Two-pack hair clip set
- Tropical floral design
- Clip closure
Style Number/Barcode: 07006-000132
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Serving Sculpted Cutout Midi Tube Dress
Serving sculpted and a little daring—this cutout midi tube dress knows how to hold attention. The ribbed knit hugs in all the right places while the cutout O-ring detail adds that extra edge for nights you’re not playing it safe.
Fit & Features
- Ribbed knit fabric, high stretch
- Strapless straight-across neckline
- Front waist cutout, metal O-ring hardware accents
- Midi-length hem, high-cut side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000334
Category Name: Vacation Looks
Price: $20.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- Sale
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Flirty Vibes Strapless A-Line Mini Dress
This is your flirty little upgrade when you want to feel instantly put-together. The strapless A-line mini dress hugs up top, skims the body, and finishes with a playful ruffle that moves with you.
Fit & Features
- Brushed knit fabric, high stretch
- Strapless sweetheart neckline
- Drop waist, ruched detailing
- Tiered ruffled design
- Mini-length hem
- Fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000697
Category Name: Vacation Looks
Price: $19.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
Product Badge:- Sale
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Vacay State Of Mind Tropical Print Maxi Dress
Vacation state of mind, no passport required. This tropical print maxi dress hugs you in all the right places with a sleek bodycon fit and bold cutout details that feel both effortless and elevated.
Fit & Features
- Knit fabric with high stretch, soft knit lining
- Tropical print
- Strapless neckline
- Triple bust cutouts and oval-shaped hardware accents
- Maxi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000622
Category Name: Vacation Looks
Price: $14.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay Mood Tropical Floral Halter Skater Dress
Booked, busy, and dressed like it. This tropical floral halter skater dress hugs just enough up top, then flares into a playful, twirl-ready silhouette made for plans that don’t end early.
Fit & Features
- Mesh fabric with knit lining, high stretch
- Tropical floral print
- Sleeveless plunging V-neckline, bar strap with beaded accents
- Halter tie-back straps
- Open back, lower tie-back spaghetti straps
- Tiered ruffled design, mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000674
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: FUCHSIA
Available Size: XS, S, M
Product Badge:- Best Seller
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Sofia Linen Halter Mini Dress
Special Occasion
Polished with a playful edge, the Sofia linen-blend mini dress is made for those effortlessly chic arrivals that still turn heads. The scallop-contrast trim halter-strap neckline and curve-hugging silhouette create a striking allure, while the mini-length hem is perfect for outdoor soirees.
Fit & Features
- Linen-blend cotton fabric, sewn-in knit lining
- Contrast trim, scallop halter tie strap neckline
- Back zipper and hook-eye closure
- Contrast trim throughout
- Curve-hugging, scallop mini-length hem
- Runs true to size
Where to Wear:
Graduations, garden parties, brunches, milestone celebrations, vacations, resorts, honeymoons, dressy occasions
Style Number/Barcode: 05001-000772
Category Name: Vacation Looks
Price: $89.90
Availability: In Stock
Available Color: KHAKI
Available Size: S, M, L
Product Badge:- Ships Free
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Bloom Mood Flower Necklace And Stud Earrings Set
This just made your outfit feel way more put together. This flower necklace and earrings set brings that flirty, polished vibe with a dainty chain and matching studs you’ll reach for on repeat.
Fit & Features
- Necklace and earrings set
- Dainty chain, flower pendant charm
- Lobster clasp closure with extender
- Flower stud design
- Post-back closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07002-000383
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: GOLD, SILVER
Available Size: NS
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Poolside Muse Bikini Halter Top
Serving beach plans with a little extra detail. This string bikini top layers into a cowl halter neck crop top with bead accents and an open back tie that feels playful, styled, and ready for sun-soaked moments.
Fit & Features
- Tie-dye print, mesh fabric
- Attached string triangle bikini top, bust lining, bead accents
- Halter cowl neckline
- Open tie back
- Crop hem
- Runs true to size
Style Number/Barcode: 06001-000725
Category Name: Vacation Looks
Price: $14.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: S, M, L
Product Badge:- Sale
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Summer State Floral Halter Top
Booked the outfit before the plans. This floral print halter top brings the heat with a plunging neckline and an open-hardware back, made for sunset dinners and beachside playlists.
Fit & Features
- Tropical floral print, mesh-lined fabric
- Plunge halter neckline with tie straps
- Open back with hardware insert
- Fitted crop hem, ruched side seams
- Runs true to size
Style Number/Barcode: 06001-000559
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
Product Badge:- Sale
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Natalia Floral Halter Formal Dress
Special Occasion
Like wearable artwork made for golden hour arrivals, the Natalia floral mermaid gown brings soft romance and sculpted elegance together in one unforgettable silhouette. Designed with a plunging halter neckline, open strappy back, and dreamy oversized floral print, it’s the kind of look that turns every entrance into a moment.
Fit & Features
- Floral pattern, knit stretchy fabric
- Halter neckline, padded bra cups
- Open back, bar accent straps and hook closure strap
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Wedding guests, vacations, anniversaries, formal milestone parties, honeymoons, destination celebrations, cocktail soirees, birthday dinners
Style Number/Barcode: 05002-000881
Category Name: Vacation Looks
Price: $29.97 $79.90
On Sale: Yes
Availability: In Stock
Available Color: LAVENDER, FUCHSIA
Available Size: XS, S, M, L
Product Badge:- Sale
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Island Twirl Crochet Mini Skort
Warning, this skort makes every walk a little more dramatic. This crochet mini skort features layered ruffle details and built-in shorts for the cutest mix of flirty and practical.
Fit & Features
- Crochet fabric, stretchy knit built-in shorts lining
- Low-rise drawstring waist tie
- Form-hugging fit
- Layered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 06501-000122
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: NATURAL
Available Size: S, M, L
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Poolside Gossip Beaded Halter Top
This top definitely gets invited everywhere. The halter crop top features beaded strap details, a flirty keyhole front, and a body-skimming fit that pairs way too well with minis, linen pants, and vacation plans.
Fit & Features
- Stretchy knit fabric
- Halter scoop neckline, beaded accents, tie straps
- Bust keyhole cutout
- Open back
- Crop fitted hem
- Runs true to size
Style Number/Barcode: 06001-000598
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Serving Curves Animal Print Cutout Mini Dress
Serving curves with zero hesitation. This animal and floral print mini dress brings the drama with a plunging neckline, sultry cutouts, hardware details, and a fit that knows exactly what it’s doing.
Fit & Features
- Lined mesh fabric with high stretch
- Abstract animal and floral print
- Sleeveless plunging V-neckline, dual hardware accents at the bust and waist
- Front waist cutout, ruched detailing
- Halter strap, open back
- Mini-length hem, fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05103-000396
Category Name: Vacation Looks
Price: $19.97 $38.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Sale
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Pretty Glow Moment Ombre Satin Clutch
Caught the light before you even walked in. This ombre satin clutch with allover colored rhinestones brings just enough shine to carry your whole look from dinner to night-out plans.
Fit & Features
- Dumpling clutch bag silhouette
- All-over colored rhinestone embellishments
- Detachable chain strap
- Top clasp closure
- Spacious lined interior
- Satin ombre-patterned material
Style Number/Barcode: 07204-000055
Category Name: Vacation Looks
Price: $16.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay Life Tropical Floral Mesh Maxi Skirt Coverup
Vacation outfit secured. This tropical floral mesh maxi skirt coverup brings the drama with a body-hugging fit, sheer finish, and side tie details that were made for beach clubs, bikini pics, and every “wait, where’d you get that?” moment.
Fit & Features
- Sheer mesh fabric, high stretch
- Tropical floral print
- Mid-rise waist
- Side cutouts, tie accents
- Maxi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 07105-000058
Category Name: Vacation Looks
Price: $10.97 $28.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: M, L
Product Badge:- Sale
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Resort Mood Floral Print Halter Top
Serving resort mood without needing the plane ticket. This floral print halter top brings the vibes with a deep V-neckline, curve-hugging fit, and open-back moment that looks so good with capris, denim, or a mini skirt.
Fit & Features
- Knit fabric, high stretch
- Tropical floral print
- Sleeveless deep V-neckline
- Halter strap, partially open back
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06002-000610
Category Name: Vacation Looks
Price: $27.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Tie Me Close Lace Maxi Skirt
A little reveal, a lot of intention. This lace maxi skirt features a front mesh wrap tie and a high side slit that moves with you and keeps the look feeling elevated but effortless.
Fit & Features
- Lace fabric, built-in knit panty lining
- High-rise waist
- Front mesh wrap tie design
- High side slit
- Form-hugging, maxi-length hem
- Runs true to size
Style Number/Barcode: 06501-000153
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L