Midi Dresses For Travel
Midi dresses for travel are your ticket to effortless style, no matter where your passport takes you. Whether you’re jet-setting across the globe or road-tripping with your ride-or-die crew, these looks are all about easy glam and go-anywhere confidence. Throw one on, snap that airport selfie, and let your outfit do all the talking—because adventure waits for no one, and neither do you.
$42.90
A sleek sage midi dress with a sleeveless cowl neckline, high slit, and stretchy knit fabric.
$59.90
A navy blue satin wrap midi dress with a cowl neckline and adjustable spaghetti straps.
$59.90
A navy blue satin midi dress with a pleated cowl neckline and high side slit.
$36.90
An elegant black off-the-shoulder midi dress with a bodycon fit and flared hem in stretchy knit.
$38.90
A white sleeveless ribbed knit midi dress featuring a V-neckline and chic high front slit.
$35.90
A mauve strapless midi dress with a cowl neckline, side slit, and curve-defining ruched seams.
$39.90
A brown knit midi dress with long sleeves, off-the-shoulder neckline, and ruched bodycon fit.
$59.90
A light blue woven midi dress featuring a corset bodice and charming lace-up back detail.
$42.90
A navy blue velvet midi dress with a sleeveless sweetheart neckline and pleated bodice.
$38.90
A sage palm leaf print midi dress in stretchy knit fabric with a V-neckline and side slit.
$46.90
A black floral midi dress with a corset bodice, sweetheart neckline, and flirty front slit.
$20.97 $46.90 55% off
A strapless sage satin midi dress with pleating and a form-hugging fit for elegant occasions.
$19.97 $42.90 53% off
A wine-colored glitter mesh midi dress with a V-neckline, ruching, and an asymmetrical hem.
$49.90
A black sheer midi dress with off-the-shoulder neckline, plunging v-neck, and high-side slit.
$44.90
A grey ribbed knit midi dress with a sweetheart neckline and twist accent, perfect for casual outings.
$20.97 $46.90 55% off
A brown leopard print satin midi dress with a sheer lace bust overlay and tie-front detail.
$36.90
A black knit midi dress with a sleeveless square neckline, ruching, and pleated mermaid silhouette.
$54.90
An elegant white mesh midi dress featuring faux pearl embellishments, off-the-shoulder neckline, and bodycon fit.
$59.90
A green satin midi dress featuring a cowl neckline, pleated bodice, high slit, and twist-back detail.
$19.97 $29.90 33% off
A mauve knit midi dress with a square neckline and form-hugging fit, perfect for any occasion.
$28 $39.90 30% off
A khaki woven midi dress with a smocked bodice, square neckline, and ruffled A-line silhouette.
$36.90
A taupe midi dress with a sleeveless square neckline, ruching, and abstract marble print.
$32.90
A chic red sleeveless midi dress with ruched seams and a flattering bodycon silhouette.
$54.90
A sage midi dress with faux pearl embellishments and an off-the-shoulder bodycon silhouette.
$34.90
A plum paisley mesh midi dress with a bodycon silhouette and flirty front slit.
$49.90
An A-line midi dress in natural woven fabric featuring a smocked bodice, pleats, and hidden pockets.
$19.97 $42.90 53% off
An ivory woven fabric midi dress featuring a ditsy floral print and lace-trimmed sweetheart neckline.
$59.90
A green satin wrap midi dress with a sleeveless cowl neckline and high-side slit.
$19.97 $35.90 44% off
A strapless taupe midi dress with a tropical print and flared hem, perfect for vacations.
$36.90
A sleek black knit midi dress with a halter neckline and flared mermaid silhouette.
$19.97 $35.90 44% off
A strapless tropical midi dress in dark marsala with a bodycon silhouette and side slit.
$35.90
A strapless white floral midi dress with a form-hugging fit and chic flared hem.
$49.90
A strapless white knit midi dress with a bold tropical floral print and form-hugging silhouette.
$44.90
An elegant black knit midi dress featuring an off-the-shoulder neckline, pleated wrap front, and thigh-high slit.
$44.90
A yellow crochet knit midi dress featuring a high halter neckline and form-hugging silhouette.
$59.90
A white floral eyelet midi dress featuring a ruffled A-line silhouette and whimsical tie-back design.
$23.97 $52.90 55% off
An alluring mauve midi dress with floral lace, off-the-shoulder neckline, and open lower back.
$59.90
An effortlessly pretty chiffon midi dress with a floral print, ruffled tiers, and smocked details.
$46.90
A black floral midi dress with a sweetheart halter neckline and flowy A-line silhouette.
$9.97 $49.90 80% off
A curve-hugging brown midi dress with a zebra print, featuring a cowl neckline and open back.
$40.90
A burgundy glitter satin midi dress featuring a lace-up back and chic faux-wrap slit.
$52.90
A white floral A-line midi dress featuring puff short sleeves, a square neckline, and a flirty front slit.
$38.90
A sleek olive knit midi dress with off-the-shoulder sleeves and a high center slit.
$42.90
A sultry red halter midi dress with a V-neckline, open back, and side slit.
$46.90
An ivory woven A-line midi dress featuring lace-up details, smocked bust, and hidden side pockets.
$59.90
An ivory cotton floral midi dress featuring puff sleeves, a V-neckline, and a flattering A-line silhouette.
$30 $42.90 30% off
A natural woven fabric midi dress with a halter pleated neckline and beaded tie waist.
$44.90
A black mesh midi dress with a cutout back, ruching, and an asymmetrical high-slit.
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Simple and sleek, this smooth knit midi dress is a perfect choice. It features a sleeveless cowl neckline, spaghetti straps, a high waist seam, a fitted, A-line silhouette, and a chic high front slit to showcase some leg. Style with embellished statement earrings for a cocktail party. Fit & FeaturesSleeveless cowl neckline, Spaghetti straps, High waist seam, Fitted A-line silhouette, High front slit, Knit fabric, plenty of stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek And Smooth High Slit Midi Dress in Navy Blue | Size: L | Knit Fabric
Wrap yourself in a glam formal dress that captivates from the moment you enter the room! Margaret features a sleeveless cowl neckline, adjustable spaghetti straps, corset seams with flexible boning, and a ruched wrap midi silhouette. The dress is composed of a satin fabric that offers a form-hugging fit with minimal stretch. Complete look with heels and rhinestone earrings. Fit & FeaturesSleeveless cowl neckline, adjustable spaghetti straps, Built-in padded bust, Corset seams, flexible boning, Ruching, wrap midi skirt, Buttery soft silk fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Margaret Formal Satin Wrap Midi Dress in Navy Blue | Size: S | Rhinestone/Satin Fabric
Radiate elegance in a formal dress that showcases your timeless style! Seona features a pleated cowl neckline, spaghetti straps, a cutout at the midriff, and a midi-length silhouette accented with a high side slit. The dress is composed of a silky-satin fabric that offers a form-hugging fit with a moderate stretch. Complete the look with rhinestone heels and a clutch. Fit & FeaturesSleeveless cowl neckline, pleating, Spaghetti straps, Cutout at the midriff, Midi-length silhouette, high side slit, Satin fabric, Form-hugging fit, moderate stretch, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Seona Formal Satin Midi Dress in Red | Size: XL | Rhinestone
Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules. Fit & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, High front slit, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfectly Stylish Sleeveless Ribbed Knit Midi Dress in Black | Size: M | Knit Fabric
Shine like a vision in the silky satin Samantha formal dress in a striking bodycon silhouette with a corset bodice that enhances your natural curves! Fit & FeaturesLined satin knit fabric, moderate stretch, Sleeveless square neckline, tank-style straps, Corset seam bodice, pleated side seam, Form-hugging silhouette, Faux wrap midi-length hem, Runs true to size, Where to Wear:Weddings, bridesmaids, cocktail parties, date nights, engagement parties, rehearsal dinner, graduations Free Shipping on All Orders Over $75. | Windsor Samantha Formal Satin Midi Dress in Navy Blue | Size: S | Knit Fabric/Satin Fabric
Channel the chic fall vibe in this ditsy floral woven midi dress featuring a sleeveless sweetheart neckline with a ruched bust and tie-front detail, thin tank shoulder straps, and a corset-style bodice. The high waist leads to a flowy A-line silhouette accented with a high-cut front slit. Fit & FeaturesDitsy floral-printed woven fabric, Sweetheart neckline, ruched bust, tie-front detail, underwire bust, Thin tank shoulder straps, Corset-style bodice with piping, high waist seam, Hidden side zipper and hook-eye closure, High front slit, Midi-length A-line fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Fall Vibe Ditsy Floral Corset Midi Dress in Brown | Size: S | Woven Fabric
Nadine Formal Ruched Satin Midi Dress in Red
$9.97 $49.90
80% off
Make a stunning impression in this satin midi dress. Elevate your night out look in this luxe stretch satin midi cocktail dress with a flattering cowl neckline for a post-worthy look. Fit & FeaturesStretch satin fabric, minimal stretch, Cowl neckline, spaghetti straps, Form-hugging fit, Ruched high side slit, Midi-length hem, Runs true to size, Where to Wear:Weddings, cocktail parties, date night, Vegas, girl's night out, rooftop bars, celebrations Free Shipping on All Orders Over $75. | Windsor Nadine Formal Ruched Satin Midi Dress in Red | Size: S | Satin Fabric
Look enchanting in this floral ruffled lace midi dress showcasing a bodycon silhouette and flirty slit for movement. Pair with heels. Fit & FeaturesSheer floral lace fabric with knit lining, moderate stretch, Square neckline, Adjustable spaghetti straps, Ruched front, Asymmetric midi-length hem with ruffled trim, front slit, Bodycon silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Enchanted Moment Floral Ruffled Lace Midi Dress in Sage | Size: XL | Lace Fabric/Knit Fabric
Make a casual-chic impression in this long sleeve ruched midi dress showcasing a folded off-the-shoulder neckline and a bodycon silhouette. Pair with heels. Fit & FeaturesSmooth knit fabrication, moderate stretch , Off-the-shoulder neckline, foldover accent, Fitted long sleeves, Ruching, Midi length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Casual Affair Long Sleeve Ruched Midi Dress in Brown | Size: S | Knit Fabric
Thrive with sweet energy in this floral midi dress perfect for brunches or dates! With a corset bodice that snatches your waist and a flirty front slit, this a-line dress will captive everyone. Pair with a necklace. Fit & FeaturesDitsy floral print, woven fabric, Wide shoulder straps, sweetheart neckline, Corset bodice, Side pockets, A-line silhouette, front slit, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Thriving Blooms Corset Floral Slit Midi Dress in Black | Size: XL | Woven Fabric
Midi Dresses For Travel
Let’s be real: when you’re living out of a suitcase and chasing adventure, the last thing you want to worry about is a wardrobe malfunction. That’s why midi dresses are the ride-or-die travel BFFs every Windsor girl needs. They’re the ultimate jet-set secret—easy to pack, impossible to wrinkle, and always ready to impress. Whether you’re hopping off a plane in Paris, twirling through cobblestone streets in Santorini, or just living your best life at a rooftop brunch downtown, a midi dress is the move. The length hits that sweet spot—long enough to keep you comfy on a breezy boat ride, short enough to let you show off those strappy sandals you impulse-bought at the airport. Midi dresses are made for those spontaneous photo ops and last-minute dinner invites, giving you that “I woke up like this” energy even after a red-eye flight. And let’s not forget about the pockets—yes, actual pockets—perfect for stashing your lip gloss, passport, or that mysterious souvenir you just couldn’t resist.
If you’re playing gift fairy for your globe-trotting bestie, or just want to treat yourself (because, duh, you deserve it), midi dresses are the ultimate present. They’re universally flattering, super versatile, and come in every vibe imaginable—from flirty florals to bold solids, and everything in between. Imagine gifting one to your sister before her study abroad adventure, or surprising your mom with a style that makes her feel like the main character on her next girls’ trip. It’s the kind of gift that says, “Go make memories, look fabulous, and don’t sweat the small stuff.” When you’re packing light but dreaming big, a midi dress is your golden ticket to effortless style. Pro tip: look for breathable fabrics that keep you cool when the itinerary gets wild, and details like adjustable straps or stretchy waistbands for those days when you go from exploring ancient ruins to dancing all night. And if you’re on the hunt for something that’ll turn heads in every time zone, check out our lineup of Unique Midi Dresses—trust, you’ll want to add at least one to your travel rotation.
Travel is about collecting stories, not stress, and your wardrobe should be just as carefree as your itinerary. Midi dresses are the MVPs of any packing list, sliding effortlessly from sightseeing to sunset cocktails without missing a beat. They’re the answer to unpredictable weather, spontaneous plans, and that “I have nothing to wear” panic. Picture yourself sipping espresso at a sidewalk café, your midi skirt catching the breeze, or watching the city lights sparkle from a rooftop, feeling totally unstoppable. That’s the magic of a great midi dress—it gives you the confidence to say yes to every adventure, and the comfort to actually enjoy it. So go ahead, book the ticket, make the plans, and let your midi dress do the heavy lifting. You’re about to make some seriously unforgettable memories, and your style will be just as iconic as the journey.