Vacation Looks

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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.

  • 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 Bag

    Fit & 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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