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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Polished Mischief Halter Top
This halter keyhole top hugs in all the right places with a sleek, sculpted fit that pairs effortlessly with shorts or skirts for concerts or weekend looks.
Fit & Fetaures
- Woven fabric
- High neckline with keyhole tie-front
- Front hook and eye fasteners
- Partial open back design
- Fitted hem
- Runs true to size
Style Number/Barcode: 06003-000368
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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Dreamy Daze Butterfly Poncho Top
Light, floaty, and a little unpredictable—in the best way. This butterfly floral poncho top with an asymmetrical off shoulder fit drapes effortlessly for that styled allure.
Fit & Features
- Butterfly floral tie-dye print, sheer mesh fabric
- Asymmetrical off-shoulder neckline
- Flowy poncho-silhouette
- Crop-length fit
- Runs true to size
Style Number/Barcode: 06001-000596
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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RSVP To Romance Floral Maxi Dress
The dress that somehow makes every plan feel worth showing up for. This floral flutter sleeve maxi dress pairs delicate ruffle details with a figure-skimming fit that's ready for bridal showers, brunch reservations, and every pretty occasion in between.
Fit & Features
- Mesh fabric with full-length lining
- Floral print
- Sweetheart neckline, ruched bust, tie detail
- Ruffled trim, short ruffled flutter sleeves
- Back zipper closure
- Maxi-length hem, form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-001265
Category Name: Vacation Looks
Price: $52.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
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Light Catching Leaf Hand Chain
The detail your outfit didn’t know it needed. This leaf rhinestone hand chain drapes just right, adding a subtle shine to complement your look.
Fit & Features
- Delicate leaf rhinestone-embellishments
- Chain design
- Finger loop
- Lobster clasp closure
- Polished shine
Style Number/Barcode: 07003-000236
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Everyday Elevated Lace Capri Pants
The capris that quietly make the outfit. These capri pants hug just right with a lace trim detail that adds a little something extra whether you’re dressing them up or down.
Fit & Features
- Smooth knit fabric
- High-rise lace trim waist
- Form-hugging fit
- Knee-length hem
- Runs true to size
Style Number/Barcode: 06502-000106
Category Name: Vacation Looks
Price: $28.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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On The List Side Slit Maxi Skirt
This is your new favorite maxi skirt for vacations or weekend fun! Designed with a sleek, body-hugging fit and a high side slit, it keeps things minimal but still turns heads.
Fit & Features
- Knit stretchy fabric
- High-rise waist
- High front slit
- Form-hugging
- Maxi-length hem
Style Number/Barcode: 06501-000152
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
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Cute Plans Wrap-Front Mini Skort
Cute plans just found their outfit. This mini skort pairs a flattering wrap-front design with fitted shorts, making it an easy pick for brunch dates, rooftop drinks, and every RSVP in between. Style with the matching tie-front top.
Shop Matching Top: Cute Plans Puff Sleeve Tie-Front Top
Fit & Features
- Linen-blend woven fabric
- High-rise waist
- Wrap-front design with mini-length overlay, tie waist detail
- Fitted shorts
- Dual back pockets
- Runs true to size
Style Number/Barcode: 06303-000063
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: RED
Available Size: S, M, L
Product Badge:- Part of a Set
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Radiant Muse Pearl Statement Earrings
Instant glow-up, no effort required. These faux pearl sunburst earrings bring that polished-meets-playful energy that finishes every outfit in seconds.
Fit & Features
- Polished finish
- Faux pearl center insets
- Post back closure
- Sunburst design detail
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000422
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- Sale
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Caught Looking Rectangular Sunglasses
A little mysterious, a little unbothered. These rectangular sunglasses are the kind you throw on when the outfit already ate, and you just need the finishing touch for coffee runs, beach days, or avoiding eye contact with your ex.
Fit & Features
- Lightweight acetate frame
- Slim rectangular silhouette
- Tinted lenses
- Metal hinge detail at temples
Style Number/Barcode: 07008-000224
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
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Text Me Tomorrow Cat Eye Sunglasses
Equal parts polished and a little hard to read. These cat eye sunglasses are the finishing touch your outfit needed for rooftop dinners, coffee runs, and pretending you’re not checking who viewed your story.
Fit & Features
- Lightweight metal frame
- Soft cat eye silhouette
- Tinted lenses
- Thin arms with minimal hardware detail
Style Number/Barcode: 07008-000239
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
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Low Key Cute Crop Vest
It’s the tiny details doing all the work. This linen blend crop vest features a dual bead tie front that lets you style it your way while keeping the vibe light, easy, and a little unexpected.
Fit & Features
- Linen-blend fabric, woven lining
- Sleeveless
- Dual bead tie front design
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06204-000156
Category Name: Vacation Looks
Price: $14.97 $32.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
Product Badge:- Sale
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No Effort Needed Aviator Sunglasses
These square aviator sunglasses sharpen any look with sleek metal frames and tinted lenses that instantly pull everything together.
Fit & Features
- Square aviator silhouette
- Tinted lenses
- Rubber nose supports
- 100% UV protection
- Polished finish
Style Number/Barcode: 07008-000237
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: SILVER
Available Size: NS
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Invite Ready Ruffle Satin A-Line Mini Dress
Cue the invite—you already know what you’re wearing. This ruffled satin A-line mini dress brings that floaty, flirty feel with just enough structure to keep it polished from brunch to wherever the day takes you.
Fit & Features
- Textured woven satin fabric
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Back zipper closure
- Front cascading ruffled design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-001384
Category Name: Vacation Looks
Price: $62.90
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
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Too Busy Booking Flights Aviator Sunglasses
Airport fit approved and iced latte ready. These oversized aviator sunglasses bring that cool without trying vibe, with a lightweight metal frame that works for beach days, errands, and every candid in between.
Fit & Features
- Lightweight metal frame
- Oversized aviator silhouette
- Tinted lenses
- Adjustable nose pads
Style Number/Barcode: 07008-000234
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: SILVER
Available Size: NS
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In Your Good Graces Halter Mini Dress
Sweet, but make it a little unexpected. This halter mini skims your shape with a soft, textured feel and a lace trim hem that adds just enough detail for showers, graduations, or dressy brunch plans.
Fit & Features
- Textured chiffon fabric, sewn in knit stretchy lining
- High halter neckline with tie straps
- Open back
- Bodycon mini silhouette
- Lace trim hem
- Runs true to size
Style Number/Barcode: 05102-000794
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
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Pretty Girls Drink Matcha Tank Top
A little caffeine, a little flirting, and suddenly the outfit is complete. This tank top keeps things cute and effortless with a fitted crop silhouette that's made for matcha runs, errands, and spontaneous plans.
Fit & Features
- Soft stretchy knit fabric
- Sleeveless scoop neckline
- Tank shoulder straps
- "Pretty Girls Drink Matcha" front script
- Fitted crop-length hem
- Runs true to size
Style Number/Barcode: 06002-000692
Category Name: Vacation Looks
Price: $19.90
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
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Pretty Breeze Floral Strappy Midi Dress
This midi dress feels like golden hour in outfit form. The tiny floral print, gathered sweetheart neckline, and open tie-back detail bring that soft, romantic vibe that always looks good at showers, graduations, and brunch.
Fit & Features
- Ditsy floral print, woven fabric
- Sweetheart neckline, tie bust
- Spaghetti straps
- Strappy open tie-back design
- A-line silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-001383
Category Name: Vacation Looks
Price: $64.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
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Sweet Escape Abstract Floral Ruffle Skort
This skort was made for sunny-day plans and spontaneous photo ops. The layered ruffle design adds dreamy movement, while the mini skort silhouette keeps it effortlessly cute from brunch with the girls to getaway adventures.
Shop Matching Top: Sweet Escape Abstract Floral Halter Top
Fit & Features
- Lightweight mesh fabrication
- Low-rise waist
- Abstract floral pattern
- Tiered ruffle silhouette
- Hidden cheeky shorts
- Runs true to size
Style Number/Barcode: 06503-000341
Category Name: Vacation Looks
Price: $34.90
Availability: In Stock
Available Color: ORANGE
Available Size: S, M
Product Badge:- Part of a Set
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Off Duty Drama Aviator Sunglasses
Big shades, iced coffee in hand, zero explanations needed. These aviator sunglasses bring that low effort chic vibes with oversized lenses and sleek metal details that instantly pull the whole look together.
Fit & Features
- Lightweight mixed material frame
- Oversized aviator silhouette
- Tinted lenses
- Contrast bridge detail with metal accents
Style Number/Barcode: 07008-000235
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
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Dreamy Vibe Floral Print Woven Midi Dress
A dress that makes even last-minute plans feel a little more curated. This floral print woven midi dress brings that effortlessly dreamy vibe with a flattering V-neckline, floaty A-line fit, and the kind of silhouette that works for brunch dates and weekend markets.
Fit & Features
- Woven fabric
- Dainty floral print
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Smocked back, zipper closure
- Midi-length ruffled hem, A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000820
Category Name: Vacation Looks
Price: $64.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
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Butterfly Kisses Mesh Maxi Skirt
Floaty, flirty, and fully saved to the outfit inspo folder. This mesh butterfly print maxi skirt hugs just right and pairs perfectly with the matching top.
Shop Matching Top: Butterfly Kisses Mesh Tie-Front Top
Fit & Features
- Butterfly print, mesh fabric, bust lining
- Long sleeves with flared cuffs
- Tie-front neckline
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06501-000124
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: TAUPE
Available Size: XS, S, M, L
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City Break Linen Blend Vest
Tailored enough to look planned, easy enough to wear on repeat. This linen blend button up vest brings a clean, structured fit that's perfect for looking polished this season.
Fit & Features
- Linen-blend fabric, sewn-in woven lining
- Four-button up front closures
- Sleeveless vest silhouette
- Faux pockets
- Tailored seams
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06204-000179
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: NATURAL, WHITE
Available Size: M, L, S
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Polka Dot Plans Halter Top
The print is playful, the fit is not here to play. This polka dot halter top brings a deep V-neckline, tie-back straps, and a curve-hugging stretch fit made for brunch detours, rooftop plans, and last-minute “actually, I’m going” texts.
Fit & Features
- Polka dot knit fabric, high stretch
- Sleeveless deep V-neckline
- Tie-back halter spaghetti straps, partially open back
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06002-000654
Category Name: Vacation Looks
Price: $22.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Clear The Calendar Jelly Flats
Cute plans require cute steps. These jelly square toe flats bring an easy slip-on finish with a sheer look that works for day dates, weekend plans, and summer trips.
Fit & Features
- Square toe
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Slip-on sheer design
- Flat sole
- Jelly material
- Runs true to size
Style Number/Barcode: 07405-000034
Category Name: Vacation Looks
Price: $18.90
Availability: In Stock
Available Color: BLACK, CLEAR, BROWN
Available Size: 5, 6, 7, 8, 9, 10
Product Badge:- New Arrival