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.
HomeVacation Looks

Vacation Looks
Product Recommendations
STYLE SPOTLIGHT
Get Eye-Catching Sandals For Women
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.
-
Beachy Vibes Bell Sleeve Tie-Front Top
This airy lightweight knit tie-front top gives off those effortless beachy vibes! It features a scoop neckline, a dual tie-front design, long flared bell sleeves, a cute scalloped front hem, and a mid-length, relaxed fit. The sheer knit fabric features a textured ribbed pattern. Layer over a basic bodysuit and style with light-wash denim.
Fit & Features
- Scoop neckline
- Dual tie-front design, thin straps
- Long bell sleeves
- Scalloped front hem
- Mid-length, relaxed fit
- Sheer knit fabric, textured ribbed pattern, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0400
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Chic Daydream Butterfly Chain Belt
Soft girl energy? Activated. This butterfly chain belt flutters right into your faves with dreamy layered charms and delicate movement—perfect for cinching your waist with a little fairycore flair.
Fit & Features
- Chain-link design
- Small and large butterfly charm accents
- Adjustable fit with lobster clasp closure
Style Number/Barcode: 07301-000144
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
-
Sangria Sunset Strapless Paisley Satin Crop Top
The perfect paisley satin crop top to wear during sunset cocktail hour! Crafted from a silky satin fabric with a summery paisley print, this crop top elevates every outfit. It features a strapless neckline and stretchy smocked back, a flirty tie design, and a pointed cropped hem that flaunts your figure. Complete the look in denim jeans and strappy sandals.
Fit & Features
- Paisley print, satin fabric, no stretch
- Strapless neckline
- Tie back design, smocked back
- Pointed cropped length
- Runs true to size
Style Number/Barcode: 06003-2545
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Floral Crush Flower Stud Earrings
Major flower power energy happening here. These flower stud earrings add the perfect flirty touch to your everyday vibe—whether it’s jeans and a tee or your fave dress.
Fit & Features
- Dainty metal flower design
- Center rhinestone embellishment
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000122
Category Name: Vacation Looks
Price: $9.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
-
Low Effort Luxe Retro Sunglasses
Instant cool-girl mode: activated. These rectangular-shaped sunglasses are giving low-effort luxe with a sleek retro frame that pairs perfectly with chunky hoop earrings.
Fit & Features
- Rectangular-shaped design
- Thin metal frame
- Thin metal arms
- Flexible nose pads
- Tinted lenses
Style Number/Barcode: 07008-000025
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Done In One Zip-Front Tie-Waist Denim Romper
Designed to be your new favorite done in one piece, this denim romper offers a cute and flattering style year-round! It's designed with classic short sleeves and collar neckline, a zip-front closure, two flap pockets and side pockets for convenience, a tie-waist belt that cinches your waistline, and a form-hugging fit. Complete the look with sleek hoop earrings and your fave sneakers!
Fit & Features
- Denim fabric, slight stretch
- Short sleeves and collar neckline
- Zip-front closure
- Two flap pockets, side pockets
- Tie-waist belt
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0400
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Minimalist Moment Two-Pack Bracelet Set
When your wrists need a glow-up. This two-pack bracelet set brings sleek, sculptural energy that’s perfect for stacking or wearing solo.
Fit & Features
- Two-pack bracelet set
- High-shine metal material
- Sleek, structured designs
- Hinge clasp design
Style Number/Barcode: 07003-000033
Category Name: Vacation Looks
Price: $14.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Lavish Leopard Print Palazzo Wide-Leg Pants
Look lavish in these leopard palazzo pants boasting a mid-rise waist and wide-leg silhouette perfect for elevating your look. Style with a crop top and heels.
Fit & Features
- Smooth woven fabric, no stretch
- Leopard print
- Elasticized mid-rise waist
- Wide-leg pant
- Pants in size small have an 11.5" front rise with a 28" inseam
- Runs true to size
Style Number/Barcode: 06402-1449
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Bloom Baby Flower Claw Clip Set
Hair game = bloomin’ cute. These floral claw clips bring the vibe, whether you're going for soft girl sweet or Y2K realness—just clip and go.
Fit & Features
- Durable material with a glossy finish
- Bold floral design with petal detail
- Claw grip closure
Style Number/Barcode: 07006-000057
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: MULTI
Available Size: NS
-
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
- Adjustable inner strings for a snug fit
Style Number/Barcode: 07302-1604
Category Name: Vacation Looks
Price: $4.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Love Of Details V-Neck Lace-Up Skater Dress
Fall in love with every chic detail of this lace skater dress sure to romance every room you walk into! With adjustable spaghetti straps and a flattering V-neckline, our dress features a lace-up mesh bodice and a playful skater silhouette. The asymmetrical ruffled trim adds a touch of flirty sophistication, making it the perfect for brides, birthday girls, or party guests! Complete the look with dainty earrings and heels.
Fit & Features
- Lace fabric line with stretchy knit
- Adjustable spaghetti straps, V-neckline
- Back zipper and hook-eye closure
- Mesh lace-up bodice
- Asymmetrical ruffles
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3436
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Breezy Sheer Lace Tie-Front Top
Cute and breezy, this sheer floral lace top features a V-neck with a tie-front design and long fitted sleeves with flared hems. Style with denim shorts and sandals for a casual summer look.
Fit & Features
- Sheer textured floral lace fabric
- V-neckline
- Tie-front design
- Long fitted sleeves, flared hems
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06202-000029
Category Name: Vacation Looks
Price: $29.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Trendy Shades Square Sunglasses
Discover these trendy sunglasses perfect for any sunny day to keep your style on point! They feature a small square shape, tinted UV protective lenses, and comfortable arms and nose support. Complete the look with platform sneakers for a casual day out.
Fit & Features
- Small square shape
- Tinted UV protective lenses
- Comfortable arms and nose support
Style Number/Barcode: 07008-1089
Category Name: Vacation Looks
Price: $9.90
Availability: Out of Stock
Product Badge:- Ships Free
-
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: $46.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: M, L
-
Weekend Feeling Sleeveless Bubble Hem Mini Dress
A sleeveless knit dress features a classic crew neckline, a form-hugging fit, and a trending drop waist seam with a bubble mini-length hem. Style with a denim jacket for casual plans.
Fit & Features
- Knit fabric, moderate stretch
- Crew neckline
- Form-hugging fit
- Drop waist seam, bubble mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5873
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Golden Nights Halter Ruffle Romper
Perfect for any occasion when you want to shine, this halter romper features a flattering form-hugging fit and playful ruffles that create movement with every step. Style with lace-up heels.
Fit & Features
- Smooth knit stretchy fabric, shorts lining
- Halter plunge neckline, tie closure
- Form-hugging fit
- Ruffled mini hem
- Runs true to size
Style Number/Barcode: 06503-000062
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: BLACK, GREEN
Available Size: S, M, L
Product Badge:- Back In Stock
-
Reusable Gel Lift Pasties
These gel bra pasties create the perfect lift and nipple coverage for a smooth look. The supportive sticky bra design with its adhesive interior gently lifts the breasts and perfectly covers the nipples for a seamless look. Wear these bra pasties underneath an open-back halter top or strapless cocktail dress with a smooth shapewear style for the ultimate flawless ensemble. Wear with a sleeveless top and a cute pair of denim for your next-day date.
Fit & Features
- One pair
- Gel pasties
- Reusable, can be worn up to 25 times
- Provide smoothing, lifting, and supporting effects
Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07101-0272
Category Name: Vacation Looks
Price: $9.90
Availability: In Stock
Available Color: NATURAL
Available Size: NS
Product Badge:- Best Seller
-
Casual Staple Ribbed Knit Bandeau Top
This casual ribbed knit bandeau top is a staple style to have in your closet. Pair with your fave high-rise bottoms or layered under cute tops!
Fit & Features
- Stretchy ribbed knit fabric
- Strapless straight neckline
- Cropped hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 07109-000001
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BLACK, WHITE
Available Size: S/M, M/L
-
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 Looks
Price: $5.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Seas The Day Pearl and Charm Statement Necklace
Giving total mermaid-on-vacay energy—and we’re obsessed. This pearl and charm necklace brings soft glam with a splash of beachy vibes, perfect for brunch plans or sunset selfies.
Fit & Features
- Faux pearl and charms
- Long chain
- Lobster clasp closure
Style Number/Barcode: 07002-000143
Category Name: Vacation Looks
Price: $9.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
-
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 Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Finishing Touch Woven Shoulder Bag
Put the perfect finishing touch to your look with this woven shoulder bag! With versatile styling options and a secure magnetic closure, you'll adore this bag all spring and summer.
Fit & Features
- Top shoulder strap
- Detachable crossbody strap
- Front flap with magnetic closure
- Spacious interior
- Woven faux leather material
Style Number/Barcode: 07203-2130
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Golden Hour Shell Toe Ring Set
Serving seaside glam with zero sand required. This 3-piece shell ring set brings the beach to your fingertips—literally. Stack 'em, mix 'em, or wear solo for a subtle flex.
Fit & Features
- Starfish, cowrie, and conch shell charms
- Coastal-inspired accents
- Pack includes three toe-rings
Style Number/Barcode: 07004-000032
Category Name: Vacation Looks
Price: $6.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
-
Kellie Strapless Ruffled Slit Lace Formal Dress
Special Occasion
A showstopping lace formal dress that exudes romance and modern elegance. Designed with a high strapless neckline, this long dress boasts a bodycon silhouette with flirty cascading ruffles and a sultry high-side slit. Complete the look with earrings and heels.
Unapologetically bold, this dress is all about confidence. Keep the luxe look going with our stunning strapless prom dresses or discover the perfect fit among our stylish wedding guest dresses.
Fit & Features
- Lace fabric lined with stretchy knit
- High strapless neckline, non-slip grip lining
- Side zipper and hook-eye closure
- High-side slit
- Bodycon silhouette
- Long-length hem
- Runs true to size
Style Number/Barcode: 05002-8961
Category Name: Vacation Looks
Price: $64.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, M, L