Discover the Best Dresses for Every May Occasion

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No matter the occasion or season, there are always plenty of opportunities to wear a dress and, of course, an overwhelming amount of options from which to pick. We’ve put together an edit of the best dresses of the month—check back every two weeks for a new selection of styles, handpicked by Vogue.

May’s edit of the best dresses of the month means there’s no better time to embrace spring and summer-ready styles that can be worn day and night, with fresh details that elevate a classic silhouette. We’re talking a mix of short- and sleeveless dresses, in lightweight fabrics, delicate prints, and pastel hues that look just as good with heeled sandals as with ballet flats or retro sneakers. There are Vogue dresses here to complement any weekend wardrobe, a range of office-ready options, plus chic styles for wedding guests, all of which pair perfectly against the backdrop of a lavish ceremony. Shop the best dresses of May, below.

The High-Fashion Floral

Two beloved spring signatures, florals and draping, come together in this statuesque silhouette. It’s the kind of dress made for a garden wedding, rooftop parties, or beachside holiday. Just add this summer’s hottest shoe–the heeled thong sandal–to complete your look.

The Summer Sparkle

Let Tory Burch’s pailette embellished dress do the talking. With all the shimmer and texture, styling it should be effortless–think a pair of flat strappy sandals, sunglasses, and a raffia bag.

The Butter Yellow Dress

La Ligne’s butter-yellow dress is simple yet impactful; its draping and drop-waist silhouette make it feel refined and modern.

The Printed Maxi

A maxi dress naturally elongates the silhouette, and this printed style from Alémais is one to wear all summer long. Style it with a sunhat, raffia tote, and sandals for a look that can seamlessly transition from city to beach.

The Everyday Linen

A linen dress cut on the bias is the ultimate summer workhorse. Dress it up with a clutch and some colorful heeled sandals or keep it casual with netted flats and a canvas tote for the office, farmer’s market, or weekend errands.

The Red Hot Dress

Every wardrobe should make room for a red dress. It’s a color that looks good on virtually everyone, without ever feeling too bold.

The Fit and Flare Dress

The contrast piping on this floral dress does more than add a detail; it defines the shape and creates an elongating effect. Make this office-ready by pairing it with a blazer and kitten-heeled sandals.

The Tie-Waist Dress

This Toteme dress is a versatile option for daytime affairs, whether paired with thong heeled sandals or minimalist glove flats–at work or on vacation.

The Strapless Dress

A cobalt blue dress is a holiday hero in the making. Clean, striking, and easy to style, it’s the kind you pack for your next holiday.

The Drop-Waist Midi

Connect the dots! Matteau’s gathered style is a charming option for Memorial Day weekend and beyond.

The Wedding Guest Dress

Wedding season is officially here! This Zara dress is an elegant and affordable option to the dress code dilemma. Just add black sandals and a simple clutch.

The Smocked Dress

Everyone knows Dôen makes some of the best summer dresses. This breezy smocked cotton-voile style is light and easy to wear on repeat, from the beach to walks around the neighborhood.

The Artful Keyhole

A spring staple with a subtle twist, Simkhai’s sleeveless white midi features an understated keyhole detail. Pair it with heeled or embellished flat sandals for instant polish—it’s a look that works for both casual outings and dressier events. Even better, brides-to-be can also wear it to one of several planned events.

The Statuesque Dress

RSVP, yes. Straight from the Tove runway—look 7, to be exact—this draped marigold dress stole the show. The color brings instant optimism, while the silhouette does all the work. Wear it to your next gala, wedding, or big event—and be prepared to turn heads.

The Ultimate Vacation Dress

Some dresses say vacation, others practically transport you to your dream destination. Loewe’s printed and draped dress is of the latter kind—whisking you away to an overwater bungalow at golden hour from the moment you slip it on. The only thing left for you to do is craft your out-of-office email.

The Butter Yellow Dress

For days when you want to look effortless without trying too hard, this butter yellow dress needs little to no styling. Just add a minimalist flat or sneaker, and you have off-duty dressing mastered.

The Lace-Trimmed Slip

The ’90s are staying put. With the delicate lace trim and sweet polkadots, this take delivers just the right amount of romance without feeling too precious.

The Paisley Mini

Doên’s scarf mini is made for an easy summer weekend. Wear it to brunch, a boardwalk stroll, or anywhere that calls for something breezy, feminine, and just a little nostalgic.

The Embroidered Floral Dress

Spring wedding invites piling up? This embroidered floral dress is an easy yes. Pair with ’90s-inspired heeled mules and a satin clutch for a pretty, not overdone look.

The Hourglass Silhouette

No waist-cinching required. Róhe’s red cotton midi creates a softly-curved, hourglass shape all on its own. Slip it on with sandals and a netted bag, and you have an effortless, warm-weather look.

The Retro Floral Print

Retro prints are back in full bloom this season, and Chloé’s Chemena Kamali went deep into the archives for inspiration. While the house is known for its bohemian spirit, these dresses nod to the 1950s couture-like shapes of founder Gaby Aghion.

The Column Dress

A little black dress is a true wardrobe essential—you can’t go wrong with one in a lightweight linen for spring and summer. The spaghetti straps and straight neckline give a subtle nod to the ’90s—we can easily image Gwyneth Paltrow or Jennifer Anniston wearing this on the red carpet—while the clean silhouette keeps it timeless.

The Drop-Waist Midi

Blush pink is having a moment—from denim to button-down shirts. This dress taps into the trend with a flattering drop-waist midi. Style it with burgundy extras for a rich combination.

The Gemstone Mini Dress

Calling all jewelry lovers, we have found your summer dress by Stella McCartney. Small gemstones swing from the neckline, like a built-in accessory—though, we won’t fault you for piling on more. Ground it with jelly shoes for extra personality.

The Abstract Floral

Consider this your sign to invest in a handkerchief dress. Cut from a crinkled cotton, this floral version is as versatile as they come. Wear it to the office, dinner, or a wedding.

The Cerulean Blue Dress

With The Devil Wears Prada 2 back in the spotlight, cerulean blue is having its moment again. This flared dress makes a case for the color. Pair with a heeled sandal and a pouch bag.

The Wrap Dress

This Khaite dress gives the illusion of separates but comes together as one effortless piece with a tie at the waist. Ground with heeled flip-flops and printed clutch.

The Fringe Trim

For those who live in black, but still want a little drama—this dress gets it right. A simple silhouette, with a fringe hem that adds movement, creates enough intrigue to make it feel intentional.

Shop the best dresses from April:

The Runway-Favorite

Tory Burch made a strong case for the off-the-shoulder jersey dress this season, sending the silhouette down its spring runway in three equally covetable shades: scarlet, blush pink, and black. Soft, sleek, and ’90s-coded!

The Romantic Lace

The slip dress gets a romantic update with contrast lace trim across the bust and hem. Where traditional slips might feel a touch revealing, this version brings a sweeter, more delicate sensibility. Pair with anything from ballet flats to sneakers.

The Mixed Media

Dries van Noten has long been a print master, and this mixed-media, pattern-clashing dress is no exception. Artful yet wearable, it feels like the kind of piece that makes an entrance at any event.

The Fringe Trim

Fringe remains one of the season’s favorite finishes, and this fit-and-flare silhouette adds just the right amount of movement. Figure-hugging in all the right places, it works just as well with flats and a woven tote as it does with heels and a clutch after hours.

The T-Shirt Dress

The T-shirt dress gets a chic makeover with an elegant twist detail accentuating the waist. In a bold red hue, this Polo Ralph Lauren style taps into one of fashion’s favorite colors.

The White Lace Dress

Simkhai’s white midi brings the season’s floral pattern to life with delicate appliqués. Romantic and refined, it’s a chic option for the bride-to-be, suitable for either an engagement celebration or a bridal shower.

The Butter Yellow Maxi

In this season’s standout butter yellow, this maxi was made for warm-weather dressing. It’s just the thing to pack for a seaside escape, perfect for cabana lunches and sunset cocktails.

The Black Mini Dress

Every wardrobe needs a go-to black mini dress; this one feels fresh with the trending tassel belt. Team it up with ballet flats and colorful raffia tote.

The V-Neck Dress

Is it really spring without a white dress? This Toteme style stands out for its raw-edge detailing and jewelry-like embellishments.

The Ruched Yellow Dress

For a dose of sunshine, opt for this ruched drop-waist dress by Bite Studios. The silhouette can be easily be dressed up or down, for a bright, mood-boosting energy no matter how you style it.

The Charming Gingham

A mini dress has never felt sweeter. Available in three colorways, this ruffled style is the kind of effortless throw-on-and-go piece that works for everything from a morning at the farmer’s market morning to a weekend brunch with friends.

The Sage Dress

Sage! Mint! Pistachio! Soft green tones are trending now. This Altuzarra dress is an elegant way to lean into the trend and feels especially right for this transitional stretch.

The Silk Mini

A mini dress is more versatile than you think. Styled on its own or layered over trousers, it works overtime with a little imagination.

The Fringe Trim

The Sir dress, complete with fringe trim at the chest, captures the sweet feeling of summer. Add a colorful sandal for a playful pop, or keep it minimal for a more refined take.

The Handcrochet Dress

Calling all beach brides! Jacquemus’s woven dress is a true work of art. Add this to your wedding moodboard, ASAP.

The Halter Dress

One ’90s silhouette you’ll soon see everywhere? The halter dress. This striped take feels especially right for now with its bubble hem maxi length. Style with a netted bag and flat sandals.

The Silk Midi Dress

The scalloped lace on this silk midi is something you need to see in person to truly appreciate.

The Blush Pink Dress

No dress roundup feels complete without a pink option, especially when the color continues to trend. This Tove maxi is event-ready yet easy to wear, with soft jersey fabrication that’s incredibly comfortable on.

The Striped Midi

There is something eternally appealing about a striped boatneck dress. Picture yourself in Nantucket, styled with boat shoes and a cardigan knotted over your shoulders as the finishing touch.

The Bateau Neckline

This Emily Dawn Long dress is a slinky jersey piece you’ll reach for again and again. The dropped-waist silhouette features a boat neckline, making it especially flattering.

The Sheer Floral

Spring has sprung! No spring wardrobe feels complete without a floral dress, and this pastel number from Khaite is the kind that works overtime, from garden weddings to outdoor soirées. Sheer dressing is one of the season’s defining trends, so consider this your chic way in. Finish with strappy sandals.

The Fluid Green Midi

If there is one brand that consistently delivers on wardrobe staples, it is La Ligne. This fluid green satin style instantly calls to mind Atonement’s iconic green dress, romantic and memorable. Pair with flat sandals for daytime or a heeled option for evening.

The Scoop Neck

An easy spring dress with just enough intrigue and elegance. Style it with a raffia bag and a flat glove shoes for a polished finish. The back cutout adds a bit of extra charm.

The Beaded Wonder

This embellished drop-waist dress feels like a bold nod to the 1920s. Equal parts glamorous and statement-making, it’s the kind of piece that invites a closer look thanks to its intricate details.

The Artiste Scarf Dress

A scarf dress always makes an impression, and this Zara style strikes that delicate balance between subtle and statement. For the office, pair it with a work tote and kitten heels, and for evening, switch to white pumps and let the dress do the talking.

The Off-the-Shoulder Dress

For those seeking something effortless, relaxed, and endlessly wearable, a jersey dress is the answer. Pair with a sneakerina for those off-duty moments.

The Modern Tailored Dress

Think of this as a feminine answer to the tailored suit. Style it out with a button-down for lightweight coverage or wear on its own for a spring day.

The Red Dress

Toteme understands the power of a beautifully draped dress, and this red style is our favorite rendition of this core silhouette yet. It folds, and falls, in all the right places.

The Funnel Neck Mini

With funnel neck jackets having such a strong moment, it feels only natural that the silhouette has made its way into dresses. The result is modern, directional, and undeniably chic—a choice pick for the minimalist.

The Marilyn Monroe-Inspired

Feminine! Playful! Nostalgic! Inspired by Marilyn Monroe’s iconic white dress, Bernadette reimagines the halter midi in a crisp pale blue poplin.

The Sporty Dress

Christopher John Rogers gives this spring dress a subtle sporty twist, with multicolored stripes across the sleeves and scoop neckline. It’s vibrant, fresh, and full of personality.

The Smocked Maxi

A mustard dress is the quickest way to bring bold color into your wardrobe. This smocked, boatneck dress by & Other Stories is a steal for under $200. Pair with neutral sandals and add a colorful bag to incorporate the color-block trend.

The Handkerchief Dress

No styling required. Mango’s handkerchief dress does all the work for you with an eyelet scarf knotted at the waist, making it one of the easiest ways to add a directional touch to your spring wardrobe with no overthinking. Pair with white derby shoes and a pouch bag.

The Silver Dress

There is something endlessly elegant about a silver dress, and this one from House of Dagmar dress feels especially modern thanks to its high V-neckline and cap sleeves—a fitting option for a night at the ballet along with opera gloves and a beaded vintage purse.

The Butter Yellow Gown

Done up in one of the season’s favorite soft hues, this pleated butter yellow dress is pure elegance. It’s gathered, sculptural construction moves beautifully with the body. Pair with a pendant necklace and a patent leather glove pump.

The Maximalist Must-Have

When it comes to bold prints and expressive color, Dries Van Noten always delivers. This dress brings exactly the right amount of vibrancy, making it a must-have for anyone embracing a more maximalist mood.

The ’90s-Inspired Maxi

Clean, simple, and quietly elegant, this minimalist jersey maxi is the kind of dress that never overcomplicates things but is always on point.

The Soft Pink Midi

A chic poplin drop-waist dress with a fitted silhouette is a chic (and rewearable!) option for all the invites rolling into your spring inbox. Pair with a kitten-heeled sandal or embellished white pump.

The Dotted Dress

RSVP, yes! Polka dots are firmly back on the fashion agenda, and we are more than ready. Consider this your next wedding guest hero.

Shop the best dresses from March:

The Striped Dress

Loewe’s multicolored striped maxi—fresh off the runway from Jack McCollough and Lazaro Hernandez’s debut collection—is finally available to shop (and so worth the wait). With its bold color palette, graphic stripes, and sweeping silhouette, it captures the season’s mood in one standout piece.

The Little Black Smocked Dress

If there’s one label we turn to time and again for beautiful dresses, it’s Dôen. This black midi, complete with a boat neckline and delicate smocking, feels feminine and effortlessly elegant.

The Something Blue Dress

For beachside brides-to-be and wedding guests alike craving something blue, this chiffon paneled dress strikes just the right note. Soft and romantic, with a subtle nod to the ’90s, it’s a dress that little accessorizing to make an impression—strappy slingbacks and a beaded clutch are all that’s needed here.

The Silk Maxi Dress

A printed maxi always makes a statement. The long-sleeve silhouette may lean more evening, but styled with a clog, it works just as well for daytime plans.

The Eyelet Dress

Going on holiday? Perhaps somewhere somewhere? This eyelet drop waist dress is just right for a long weekend in the Bahamas—complete with playfully embellished sandals and a loose itinerary.

The Halterneck Dress

What’s a spring and summer wardrobe without a halterneck dress? Minimal yet impactful, this style brings effortless polish to daytime (or evening!) plans. For in-between weather, layer a leather jacket on top and slip into metallic ballerinas—a combination that’s equal parts sensible and modern.

The Sporty Inspired Dress

Sporty dressing is everywhere this season, and Miu Miu’s jersey mini dress nails the look with its signature tongue-in-cheek charm. (It’s all in the zip-up detail and stand collar!) Style it with New Balance x Miu Miu sneakers for the full effect.

The Graphic Polka Dot Dress

Junya Watanabe’s polka-dot dress feels like wearable mixed-media art. With its graphic spot, lace detailing, and draped bodice, it offers an expressive—and trend-forward—take on occasion dressing.

The Mint Printed Dress

With spring around the corner, this cotton poplin dress by Rosie Assoulin, mixed with floral and stripes, does the work for you. It’s a statement on its own; all it needs is your favorite flat or sandal.

The 1920s-Inspired Dress

With its swishy fringe and intricate beading, Bode’s rendition of the drop-waist dress feels like a modern heirloom—either styled with a pouch and kitten heels for a striking evening look, or studded oxfords for an unexpected daytime twist.

The Ribbed Knit Dress

A ribbed knit midi is a warm-weather staple for a reason, and this Proenza Schouler option feels especially fresh. Cut in a flared silhouette in a vibrant citrus hue that nods to Rachel Scott’s knitwear prowess, it’s the kind of piece you rewear with no second guessing.

The Long-Sleeved Polo Dress

A polo dress is a one-and-done solution when you little time to spare but don’t want to sacrifice polish. We love this Madewell midi, with its sheer sleeves, for transitional dressing.

The Floral Maxi Dress

Little livens up a wardrobe quite like a floral dress. This Emilia Wickstead maxi is a graceful option for any event on your calendar. A kitten heel, embellished clutch, and soft pink lip are your finishing touches.

The Runway Dress

If anyone understands the art of crafted dress, it’s Fforme. From the sculptural drop-waist silhouette to its sleek, body-skimming shape, the Zaria midi stands out as an unapologetically elegant choice, fit for the office, evening, and beyond.

The Drop Waist Dress

Gabriela Hearst’s Isai dress feels like the epitome of spring dressing. Crafted in linen and silk—it only looks like denim!—its low back and fluid drop waist allows for various styling possibilities. Take cues from the label’s runway show and wear it with a long pendant necklace and flat sandals for understated sophistication.

The Polka Dot Dress

Spotted in more spring collections that we can count, polka dot is a print that isn’t going anywhere. Whether styled with boots now or sandals later, it is a classic that always feels relevant—as inconspicuous stipples, or full moons.

The Poplin Tunic Dress

There is nothing quite like an easy poplin dress. Light, airy, and endlessly versatile, it works just as well for the office as it does for a seaside escape.

The Sculptural Dress

Róhe’s hourglass linen and silk dress delivers drama in a quiet and refined way. Its sculptural shape feels modern and considered—contrast with a colorful pouch and silver pendant.

The Sheer Printed Dress

A study in lightness and movement, Altuzarra’s printed sheer dress features a knife-pleated skirt and an effortless, fluid silhouette. It’s the kind of piece that transitions seamlessly from office to event dressing. Slip into ballet flats and a tailored blazer for your 9-5; swap in heels and a chic clutch for evening.

The 1920s-Inspired Dress

The return of the flapper dress feels both modern and nostalgic, and Dries Van Noten’s interpretation—a blush pink midi with delicate vining floral embellishments—feels especially right for spring. Wear it the way Daisy Buchanan might: with pearls, pointy kitten heels, and a beaded bag, for your next event.

The Floral Dress

J.Crew nails easy polish with this sweet bias-cut slip, featuring an allover floral print. Take cues from Jane Birkin and pair it with a woven basket bag and minimal sandals.

The Scarf Dress

Few silhouettes feel as inherently elegant as a scarf dress. This draped Acne Studios midi, rendered in an icy blue, reimagines the asymmetrical dress with fluid movement and a long wrap-around sash that’s quietly striking.

The Mini Wrap Dress

With its abstract motif and robe-like ease, the mini wrap dress feels both polished and playful—especially when teamed up with black flats and space-age sunglasses for contrast.

The Butter Yellow Mini

Minimalists rejoice! The appeal of this Cos mini lies in its twist sleeve—a subtle yet striking detail that elevates an otherwise simple silhouette. Pack it in your carry-on for a sunny weekend in Cabo.

The Drop-Waist Dress

Tove knows how to design dresses that make women feel elegant and regal, whether they’re for a warm spring day at the office or a sophisticated black-tie affair. The Sabi gown feels fit for either scenario, styled with soft loafers or sharp wedges.

The Cobalt Statement

A burst of blue will electrify your wardrobe—not to mention your mood. This asymmetric dress from Proenza Schouler, complete with a low-cut back and fixed pleating at the hip is an artful homage to the chrysanthemum, realized in abstract brush strokes for a blurred effect.

The LBD

The forever closet go-to. A simple black dress remains the ultimate timeless option; this one from Tory Burch features a contrasting brown neutral sash. Find inspiration in Carolyn Bessette-Kennedy’s understated approach to evening wear and pair with black Manolo Blahnik heels for an elegant finish.

The Striped Shirtdress

A long-sleeve shirtdress is the ultimate work-to-weekend essential. Comfy and versatile, let this find be a reminder that practicality and style can coexist—all for under $100.

The Pink Dress

Leave it to Jacquemus to capture the essence of what women want to wear, at exactly the right moment. Fluted pleats and corset-inspired detailing balance structure and volume, resulting in a dress that feels at once whimsical yet refined.

The Reimagined Animal Print

Ferragamo’s spring collection just dropped—and in it is Look 7—a striking take on animal print in a 1920s-inspired silhouette, where cobalt blue, floral, and fringe come together in bold but not over the top way.

The Geometric Mock-Neck Dress

A mod revival, courtesy of Prada. This brown geometric mini with a mock neckline feels sharp yet directional. Pair with boat shoes and an array of ankle charms for Mrs. P-coded charm.

The Red Drape Dress

Here’s an evening option you can actually rewear, whether it’s for a cocktails-and-dinner or a suite of wedding RSVPs this summer. Between the artful draping, warm terracotta hue, and open-back detailing, this silk dress is sultry romance and head-turning drama all in one.

The Bandana Dress

Dôen’s take on the scarf dress is the perfect everyday option—a laid-back bandana-inspired print, with a relaxed cut that lends itself well to styling with ballet flats, kitten heel pumps, or lace-up sandals.