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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Boho Chic Straw Platform Block Heels
Platform and boho chic, these block heels were made for fun under the sun! Pack these essential shoes for vacations, weekend trips, or a beach day. They feature an almond toe, an adjustable ankle strap with buckle closure, and a platform sole to elevate the style. Complete the look with the matching hat and bag!
Shop Matching Hat: Boho Chic Tiered Floppy Straw Hat
Shop Matching Shoulder Bag: Boho Chic Straw Shoulder Bag
Shop Matching Tote Bag: Boho Chic Crossbody Straw Tote BagFit & Features
- 3.5" Block heel
- Almond toe
- Adjustable ankle strap, buckle closure
- Platform sole
- Luxe fit cushioned insole
- Straw material
- Runs true to size
Style Number/Barcode: 07401-4659
Category Name: Vacation Looks
Price: $20.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Irresistibly Sweet V-Neck Floral Chiffon Maxi Dress
You'll be irresistibly sweet in this floral chiffon maxi dress at showers, graduations, or semi-formal events! The V-neckline and spaghetti strap tie accentuate your frame while the flowy maxi silhouette adds a touch of elegance. With a front slit and floor-length hem, this dress is perfect for any occasion. Complete the look in espadrille wedges.
Fit & Features
- Floral print, chiffon fabric lined with woven fabric
- V-neckline
- Spaghetti strap ties
- Front slit
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-3301
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Get Cutesy Faux Leather Sherpa Bucket Hat
Get cutesy with your outfit in this faux leather bucket hat perfect for bringing the cozy vibes! The hat features a classic bucket hat styling with a faux sherpa trim. Complete the look in a cozy jacket on a chilly day!
Fit & Features
- Faux leather exterior
- Classic bucket hat styling
- Faux sherpa trim
Style Number/Barcode: 07302-1488
Category Name: Vacation Looks
Price: $3.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Posh And Pretty Strapless Bow Ponte Crop Top
You'll draw everyone will this posh and pretty ponte crop top! Designed with a sleek strapless neckline and front bows with cutouts, this top will turn heads.
Fit & Features
- Ponte knit fabric
- Strapless neckline
- Front bows with cutouts
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000124
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Quite A Bell Sleeve Crop Sweater
Your new favorite crop sweater to create all sorts of trendy outfits! It features long bell sleeves, a mock neck, and a center front slit accent, and is composed of a rib-knit fabric with minimal stretch. Style with flare denim jeans to complete the look.
Fit & Features
- Long bell sleeves
- Mock neck
- Center front slit accent
- Cropped hem
- Sweater rib-knit fabric
- Minimal stretch
- Runs true to size
Style Number/Barcode: 06005-1812
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simply Sunny Scoop Neck Skater Eyelet Mini Dress
Sunshine days are ahead and this skater mini dress is perfect for enjoying the weekend and weather! Crafted from an adorable eyelet knit fabric, this mini dress is designed with a flattering scoop neckline, adjustable spaghetti straps for a perfect fit, and a flirty tie-back detail to show off your style. The skater silhouette and tiered ruffled hem allow for movement and a fashionable sway with every step! Complete the look in heeled sandals.
Fit & Features
- Eyelet knit fabric, sewn-in knit lining
- Adjustable spaghetti straps
- Tie-back detail
- Skater silhouette
- Tiered ruffles
- Runs true to size
Style Number/Barcode: 05102-5426
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Coastal Style Woven Tie-Waist Wide-Leg Pants
Capture that coastal-chic style with these breezy tie-waist wide-leg pants. Designed with an airy lightweight woven fabric, they feature a high-rise waist with an elasticized back waistband for added stretch, a side tie accent, and a flowy wide-leg silhouette. Pair with a basic crop top and strappy sandals.
Fit & Features
- Airy woven fabric, no stretch
- High waist, elasticized back waistband
- Side tie detail
- Wide-leg fit
- Runs true to size
Style Number/Barcode: 06402-1409
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Traveling Cute Halter Wide-Leg Cargo Jumpsuit
Travel cute wherever you're heading in this sleeveless woven jumpsuit for a chic and polished vibe! The halter collar neckline and front zipper closure provide a classic and utility touch, while the open back with an adjustable strap flaunts some skin, and side and flap pockets offer functionality along the wide-leg silhouette. Complete the look with a trendy shoulder handbag.
Fit & Features
- Woven fabric
- Front zipper closure
- Open back, adjustable strap
- Side pockets, flap pockets
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06402-1407
Category Name: Vacation Looks
Price: $24.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Now In Bloom Open Back Floral Maxi Dress
A sultry open back you'll adore with chic floral blooms! This maxi dress captures attention with its flattering cowl neckline and curve-hugging silhouette, perfect for shower celebrations and dressy events!
Fit & Features
- Floral print, mesh-lined fabric
- Cowl neckline
- Spaghetti strap ties
- Open back
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000023
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Vibes Faux Sherpa Shacket
Layer on all the cozy vibes with this trendy faux sherpa shacket! It features a collared neckline, long sleeves, a button-down front, buttoned chest pockets, side pockets, and a relaxed oversized fit for that ultra-comfy feel. The soft faux sherpa fabric includes a cotton-blend lining. Pair this adorable shacket over a basic bodysuit with faux leather leggings and combat boots!
Fit & Features
- Collared neckline
- Long sleeves, single button detail
- Complete button-down front
- Dual buttoned chest pockets
- Dual lined side pockets
- Faux sherpa fabric, cotton-blend lining, minimal stretch
- Relaxed oversized fit
Style Number/Barcode: 06201-0408
Category Name: Vacation Looks
Price: $9.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dainty Cubic Zirconia Evil Eye Charm Necklace
Radiate and sparkle with positive energy in this delicate evil eye charm necklace! It features a dainty chain with an evil eye charm embellished with mini cubic zirconia stones and beaded detailing for a pretty vibe. Style with hoop earrings and strappy sandals.
Fit & Features
- Dainty chain
- Evil eye charm
- Mini cubic zirconia stones, beading
- Back adjustable chain with lobster clasp closure
Style Number/Barcode: 07002-1777
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Simplicity Open-Circle Charm Necklace
Effortlessly elevate your looks with this sleek charm necklace, a chic simple accessory for every day. It features a dainty chain with a delicate open circle charm at the center. Style with hoop earrings.
Fit & Features
- Dainty chain-link design
- Center open-circle charm
- Back adjustable chain with lobster clasp closure
Style Number/Barcode: 07002-1807
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Second Look Turtleneck Open Back Sweater
This cozy crop sweater will make everyone do a double-take! Featuring slouchy long sleeves with ribbed cuffs, a turtle neckline, and a cute surplice open back design on a relaxed silhouette on ultra-soft knit fabric. Complete the look in a mini skirt and your favorite boots for a coffee date or pumpkin patch.
Fit & Features
- Long sleeves, ribbed cuffs
- Turtle neckline
- Surplice open back
- Relaxed silhouette, cropped hem
- Ultra-soft rib knit sweater fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1744
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty In Floral Sweetheart Bodycon Mini Dress
Step out in this flirty floral mini dress for Valentine's Day, dates, and parties! Showcasing a ditsy floral print on soft brushed knit fabric, this dress features a bust tie keyhole, side ruching, and a bodycon fit, to accentuate your figure. Complete the look with a mini purse and heels.
Fit & Features
- Ditsy floral print, brushed knit fabric with stretch
- Spaghetti straps
- Bust tie keyhole
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5523
Category Name: Vacation Looks
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Bliss Tie-Back Slit Maxi Dress
Ideal for making a statement at any occasion, this artsy print maxi dress combines chic with effortless style. Featuring a flattering A-line silhouette and a stylish front slit, this dress offers a breezy look that turns heads with a tie-back design.
Fit & Features
- Artsy print, woven fabric, stretchy knit lining
- V-neckline
- Adjustable spaghetti straps
- Tie-back design
- A-line silhouette
- Front slit, flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6039
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High Rank Camouflage Cargo Shorts
Show off your high-ranking status as a fashion commander! These camouflage twill shorts feature a flattering high-rise waist, cargo-style flap pockets with pull-tab closures, and a short-length hem on twill woven fabric with a slight stretch. Complete the look in a basic tank top and your favorite white sneakers!
Fit & Features
- High-rise waist
- Cargo-style flap pockets, pull-tab closures
- Short-length hem
- Front button and hidden zipper closure
- Belt loop accents
- Camouflage print, twill woven fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06303-0232
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cozy Stroll Colorblock Fringe Blanket Scarf
Layer on this adorable colorblock fringe blanket scarf for a cozy stroll to grab coffee! Composed of a soft fuzzy woven material with trendy fringe hems and a cute colorblock pattern, this long scarf is a stylish staple for the season. Pair with a trench coat and booties.
Fit & Features
- Soft fuzzy woven material
- Long fringe hems
- Long design
- Colorblock pattern
Style Number/Barcode: 07305-0471
Category Name: Vacation Looks
Price: $3.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Total Trend Long Sleeve Checker Crochet Sweater
With this crochet sweater to layer over your outfit or swimsuit, your looks will always be on point! The flare cuffs add a touch of femininity, while the open front with tie closure allows for a customizable fit. The cropped hem and checker pattern make this sweater a stylish and versatile addition to your wardrobe. Complete the look with sunnies.
Fit & Features
- Sheer crochet fabric
- Checker pattern
- Open front with tie closure
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-1978
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Get Spotted Cow Print Faux Fur Scarf
Get spotted in this cute cow print scarf as you walk downtown! The trendy scarf features an all-over cow print pattern on a super soft faux fur material. Style with the adorable hat.
Shop Matching Hat: Trendsetting Look Faux Fur Bucket Hat
Fit & Features
- Cow print pattern
- Faux fur material
Style Number/Barcode: 07305-0465
Category Name: Vacation Looks
Price: $4.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreamiest Summer Smocked Floral Chiffon Midi Dress
Have the dreamiest summer romance in this floral chiffon midi dress perfect for dates and parties! This dress features a square neckline, adjustable spaghetti straps, and a stretchy smocked bodycon silhouette for a comfortable and flattering fit. The tiered ruffled midi-length hem adds a touch of femininity, while the floral print on chiffon fabric gives the prettiest look. Style this floral dress with earrings and block heels.
Fit & Features
- Floral print, chiffon fabric
- Adjustable spaghetti straps
- Square neckline
- Stretchy smocked bodycon silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05101-2985
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cozy Elevated Faux Sherpa Trim Vest
This faux sherpa trim vest is a cozy elevated staple for the season! It features a lapel collar, an asymmetric zip-front design, a cropped hem, a fitted silhouette, and faux sherpa trims on the ultra-smooth faux suede fabric. Layer over a long-sleeved bodysuit with jeans and ankle booties for a chic fall vibe.
Fit & Features
- Sleeveless bodice, lapel collar
- Asymmetric zip-front design
- Two front faux pockets
- Cropped hem, fitted silhouette
- Faux sherpa trims
- Faux suede fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06201-0395
Category Name: Vacation Looks
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sun Chaser Stiletto Buckle Mules
Laid-back but luxe, these rafia mules were made for rooftop hotel brunches and dinners by the beach. The chic buckle detail and stiletto heel make them an easy upgrade to your weekend look.
Fit & Features
- Stiletto heel
- Square toe
- Wide dual straps, one with a buckle accent
- Cushioned insole
- Rafia material
- Runs true to size
Style Number/Barcode: 07401-000532
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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In Love Lace-Up Knee High Boots
Fall in love with these faux suede boots with endless styling possibilities! They feature an almond toe, inner zipper closure, a short block heel, and a knee-high shaft with a trendy lace-up back. Complete the look in a chic trench coat for a dinner and show downtown!
Fit & Features
- Almond toe
- Inner zipper closure
- Short block heel
- Knee-high shaft, lace-up back, tie closure
- Faux suede material
- Runs true to size
Style Number/Barcode: 07402-0964
Category Name: Vacation Looks
Price: $12.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Blissful Aura Floral Ruffle Maxi Dress
Serve a blissful aura in this floral maxi dress while on vacation or for weekend fun! The delicate V-neckline accentuates your figure, while the form-hugging fit flatters your curves with a bold ruffled design.
Fit & Features
- Floral print, mesh fabric, sewn-in knit lining
- V-neckline, spaghetti straps
- Form-hugging bodice
- Ruffled maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000054
Category Name: Vacation Looks
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free