The Best Midi Dresses

Every wardrobe can benefit from a classic slip dress, and this midi dress by The Drop is all timeless style. A slip dress like this can be worn so many ways — paired with heels and a clutch, it’s a chic evening dress; with sneakers and a baseball cap, it’s an adorable weekender. Basically, there’s nowhere this dress can’t go. It’s available in so many fun colors — from wear-with-anything neutrals to daring shades, like chartreuse and fiery orange — so you may want to pick up a few.

• Available sizes: XX-Small — 5X
• Available colors: 21

The menswear-inspired collar and checkered print of this midi dress by Danish designer BAUM UND PFERDGARTEN are perfectly in-step with current fashion week trends. Partially lined, side-slitted, and rendered in a modern mesh fabric, this dress never feels overly retro, although the A-line shape and collared, buttoned neckline are ‘60s-chic in all the best ways. The vibrant green color also taps into a major color trend this year. Wear with sneakers as shown on the model, or try it with a heeled Mary Jane.

• Available sizes: XX-Small — X-L
• Available colors: 1

Daily Ritual’s V-neck midi dress is a cheat, in all the best ways: The jersey material boasts the oh-so-comfy feel of your favorite T-shirt, while the fitted-yet-relaxed shape and subtle high-low hem offer the structure of a dress. You’ll live in this easy-breezy dress in warmer temps; when it gets chillier, it’ll look cute paired with a denim jacket. And since the length is a bit shorter than other midi dresses, this works well for both petite and taller frames.

• Available sizes: X-Small — XX-Large
• Available colors: 11

This classic midi dress would be perfect for conservative settings like the office, but that in no way limits its possibilities. The peasant sleeves, flounced hem, and subtle striped print are playful details that make it just as suitable for lunch, running errands, or a picnic in the park. One Amazon reviewer summed up the versatility of this dress, writing, “this dress looks high end. It feels high end. The cost is unbelievable for what you get. The perfect length, flowy, lightweight.” Choose from eight colors, like sage green, mustard, and navy.

• Available sizes: X-Large Plus — 4X-Large Plus
• Available colors: 8

This midi dress by Ulla Johnson is the sort of heirloom quality piece you’ll keep forever. Ulla Johnson has been thoughtfully crafting garments since 1998, and the textured ruffles, flounced hem, and sophisticated floral print of this dress make it one you’ll reach for time and time again. In warm weather, wear it with strappy sandals (heels or flats; either will look great). In cold weather, you can layer it over a turtleneck and pair it with knee-high boots.

• Available sizes: 00 — 14
• Available colors: 2

This knit midi dress offers all the comfort of lounging in a giant cardigan in the form of an uber-chic dress. A side slit and sultry V-cut back add just enough spice to qualify this dress for a low-key dinner, too. Whether paired with booties or loafers for the office, or sneakers or slides on weekends, you’ll feel comfy and sophisticated. You have five muted shades to choose from: ecru (pictured), black, gray, dusty pink, and the dreamiest sky blue.

• Available sizes: XX-Small — 5X
• Available colors: 5

Between the close-fitting silhouette, keyhole cutout, and playful color, this midi dress from Line and Dot would be incredible be for a date. Meanwhile, the midi-length and comfy, stretchy knit fabric lend this piece a sense of ease; it’s the sort of dress that will make you look effortlessly good. And it will pair well with virtually any shoe style, so you’ll be ready for whatever that date throws at you, whether that’s heels, a gleaming white sneaker, or even a lug-sole boot. Add a button-down cardigan to play up the sweet vibe.

• Available sizes: X-Small — Large
• Available colors: 1

The high neck and elbow-length sleeves of this midi dress might be all business, but the curve-hugging silhouette, rendered in classic Bond-Girl-black, is 100% pleasure. Wear it to the office with a slick leather loafer, then change into stilettos and swap in a statement necklace for an evening out. It’s available in a few other solid colors, as well as two prints, but black is such a classic (hello, new favorite LBD).

• Available sizes: Large — 5X-Large Plus
• Available colors: 10

Paired with some strappy sandals and mussed hair, this ribbed tank dress would do Carrie Bradshaw proud; layer on some jewelry, toss in a little smudged eyeliner, and you’re ready for cocktails. But it’s got weekend energy, too — this dress would ooze effortless cool when paired with flat sandals, chunky sneakers, or some booties. It’s great for layering, too.

• Available sizes: Small — X-Large
• Available colors: 11

The ruffled neckline, off-the shoulder sleeves, and sweet floral print of this nap-style midi dress are perfect for picnics or garden parties; it’s not that you need this dress to eat tiny sandwiches and drink from a champagne coup, but it sure will make it more fun. The sleeves can be worn on or off the shoulder for added versatility. And while the floaty floral details of this dress would be magic in warm weather, colder weather doesn’t fully rule this dress out; just layer the yellow or gray options over a turtleneck and tall boots.

• Available sizes: X-Small — X-Large
• Available colors: 8

Everyone needs a foolproof cocktail dress, and it’s hard to imagine a soirée this lacy midi dress wouldn’t improve. It strikes a balance between elegance and sensuality; lace layered over an opaque sweetheart lining offers a hint of sultriness, but the midi cut and elbow-length sleeves (adorned with sweet scalloped edges) keep things elegant. Available in several chic colors, this dress is just the thing for your millionth wedding of the season.

• Available sizes: 14 Plus — 28 Plus
• Available colors: 9

Goodthreads’ midi dress is precisely the piece you’ll want to add to your roster of brunch/bridal shower/birthday party looks. But you’re hardly limited to the aforementioned events: The timeless A-line silhouette combines with delicate camisole straps and a swingy skirt to create a dress versatile enough to pair with a sweater and loafers for the office, or a pair of strappy sandals for cocktails. More to love? A sweet smocked back, breathable Georgette fabric, and handy side pockets.

• Available sizes: X-Small — XX-Large
• Available colors: 10

This slinky black midi dress will surprise you with its versatility. The form-fitting silhouette and still-trending cutout detail at the collarbone make it the perfect thing for a night out. But the ribbed sweater material keeps this from veering too far into clubbing territory, so it’ll pair nicely with simple leather loafers and a blazer for a more covered-up affair.

• Available sizes: XX-Small — 5X
• Available colors: 2

The mid-length and neutral tones of this midi dress offer tons of versatility, but there are so many details that make it feel special — the flouncy skirt and blousy peasant sleeves combined with that adorable gingham and smocking will have you feeling like you’re on vacation in the Tuscan countryside. The smocked bodice is embellished with sweetly scalloped Chantilly lace and black sequins, so this dress can seamlessly transition from day to night. Try it with moto-inspired slides as shown on the model, or a slim, lace-up biker boot. This is a dress with structure and shape, but also that enviable quality most associated with luxury: ease.

• Available sizes: X-Small — X-Large
• Available colors: 1

This midi dress is chock-full of timeless details. A simple A-line shape, midi length, and slim long sleeves are all classic elegance; that sweet tie at the neckline lends the dress a bit of a vintage sensibility, while the houndstooth print keeps it current. Plus, it has pockets (who doesn’t love pockets?), and 4% elastane blended into the fabric means you’ll get some stretch and movement. The slim long sleeves mean you can layer a sweater on top if you get chilly without adding much bulk.

• Available sizes: X-Small — X-Large
• Available colors: 4