20 Stylish Shirtdresses Worth Adding To Your Wardrobe Right Now

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by Julia O'Donnell
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It’s not hard to see why the classic shirtdress has stood the test of time. Versatile and effortlessly cool, the menswear-inspired design looks great on literally everyone and can be worn countless ways, so it never really goes out of style or feels out of place. In other words, the best shirtdresses are basically the definition of wardrobe staples — so if you don’t have at least one hanging in your closet, consider this your reminder.

To make shopping for a great shirtdress feel just as effortless as wearing one, look no further: Here, you'll find 20 of the best shirtdresses on the market right now, and conveniently, they can all be purchased on Amazon Fashion. Whether you love classic, oversized shirtdresses that stay true to their menswear roots or prefer something a bit more tailored, you’re bound to find something that suits your personal sense of style here. And while some of these shirtdresses cost as little as $25, there are plenty of luxury picks — from brands like Calvin Klein, GANNI, Ramy Brook, and Tahari — to choose from as well.

Ready to meet your next wardrobe MVP? Then keep reading to browse 20 of the most stylish shirtdresses worth adding to your closet right now.


The Classic, Versatile Shirtdress That Belongs In Every Wardrobe

You can't go wrong with a classic, menswear-inspired shirtdress like this one. White is an absolute essential, but it's worth adding a few other colors to your wardrobe as well. That said, depending on your height and how long (or short) you prefer your dresses, this may require a pair of leggings or tights underneath.

  • Available sizes: Small — XX-Large
  • Available styles: 18


An Asymmetrical Shirtdress Made Of Cozy Flannel

A floaty silhouette and asymmetrical hemline give this cozy flannel shirtdress a unique, stylish touch. Tall boots will complement the irregular hem beautifully, and you could try cinching the waist with a leather belt, too. It's worth noting that this design is available in several other plaid prints, so it's worth checking out the other options if you're not a fan of this one.

  • Available sizes: Small — XX-Large
  • Available styles: 11


A Utility-Chic Shirtdress That Can Be Dressed Up Or Down

This utility-style shirtdress is made of tencel lyocell, the eco-friendly fabric that sustainable brands like Reformation love. Design highlights include two chest pockets and a self-tie belt, and it's sold in two denim washes, in addition to the army green color pictured. Dress this up with heels and some chunky gold earrings, or dress it down with simple white sneakers.

  • Available sizes: 2 — 16
  • Available colors: 3


A Lightweight, Belted Shirtdress With An Off-The-Shoulder Neckline

This stylish shirtdress has lots of clever design details that set it apart from the rest, like an off-the-shoulder neckline, an asymmetrical collar, a built-in tie belt, and rows of tiny buttons at the hip and sleeves. It looks a lot more expensive than it actually is, and the fact that the belt is adjustable makes it easy to achieve the perfect, custom fit.

  • Available sizes: 4-6 — 12
  • Available colors: 3


A Classic Calvin Klein Shirtdress That Comes In Lots Of Stylish Prints

This fit-and-flare shirtdress from Calvin Klein is destined to become a staple in your work-to-weekend wardrobe. It's made of a light, airy blend of linen and viscose, and has cute touches like a self-tie belt and buttons down the front. It also comes in several chic colors and prints, and — best of all — has two, roomy side pockets.

  • Available sizes: 2 — 14
  • Available colors/prints: 6


This Lightweight Shirtdress That Makes The Perfect Swimsuit Cover-Up

There are so many different ways to wear this lightweight, slightly sheer shirtdress: as a swim cover-up or floaty summer dress, layered under a blazer with a waist-cinching belt and leggings, or paired with denim cutoffs for casual, warm-weather outings. Made of a soft, breathable blend of rayon and spandex, it comes in a ton a gorgeous colors and prints, ranging from crisp, classic white to leopard print and tie-dye.

  • Available sizes: Small — 3X-Large
  • Available colors/prints: 28


This Denim Shirtdress With Western-Inspired Details

This denim shirtdress is Levi's iconic Western Shirt in dress form — and it has all the effortless versatility that made the original shirt such a staple. Crafted of sustainably produced denim and finished with snap buttons and a thin leather tie to cinch the waist, it'll pair perfectly with slouchy boots and sneakers alike.

  • Available sizes: 1X — 3X (X-Small — X-Large here)


A Jersey Wrap Dress That's Perfect For The Office & Events

Combining the best of a wrap dress and a shirtdress, this Lark & Rock frock is a must for every wardrobe. Crafted of a lightweight jersey fabric that drapes and moves beautifully, it'll look great with pumps or ankle boots for an easy work outfit, and can easily be dressed down with white sneakers for a slightly preppy, casual look.

  • Available sizes: X-Small — XX-Large
  • Available colors: 6


A Super-Chic, Little Black Shirtdress That'll Never Go Out Of Style

Another pretty, polished shirtdress from Calvin Klein, this one has a midi length and a more tailored, fitted silhouette. A true wardrobe staple, it's sure to bring in dozens of compliments when you wear it to work, and can easily be dressed up or down for a whole range of other occasions, too. Plus, the pointed collar, A-line silhouette, and waist-cinching belt give it a vintage look that'll pair equally well with tall boots or classic pumps, so you'll have no problem wearing it all-year round.

  • Available sizes: 2 — 14


A Classic Cotton Shirtdress That's Floaty & Breathable

Easy and breezy, this swingy shirtdress looks put-together enough to wear anywhere, yet feels as comfortable and unrestrictive as an oversized T-shirt. A pleated detail in the front ensures the silhouette will move beautifully along with you, and the 100% cotton fabric is both durable and breathable. It'll look great with sandals all summer long, and can easily be paired with tights, ankle boots, and a jacket when the weather gets cooler.

  • Available sizes: 14 Plus — 32 Plus
  • Available colors: 3


This Cute Shirtdress & Sweater Dress In One

Polished and preppy, this chic English Factory dress combines a mini-length shirtdress and tunic sweater into one stylish piece, complete with a pretty velvet bow tied at the neck. It makes it easy to nail the perfect layered look every time, whether you play up the look with Oxfords or ballet flats, or add chunky combat boots for a more unexpected juxtaposition.

  • Available sizes: X-Small — X-Large
  • Available colors: 2


An Oversized Shirtdress With A Cinched Waist & Statement Sleeves

The wide belt on this statement-making shirtdress is long enough to wrap around the waist several times, creating a cinched, almost corset-like effect. Featuring voluminous lantern sleeves, a crisp shirt collar, and buttons, it can be dressed down with sneakers or dressed up with knee-high boots or pumps.

  • Available sizes: Small — 3X-Large
  • Available styles: 8


This Stylish Leopard Shirtdress From GANNI

Practically every GANNI piece is a total showstopper, and this leopard-print shirtdress is far from an exception. The textured jacquard fabric lends structure to the boxy top and short, pleated skirt, creating a slightly exaggerated silhouette that feels unexpected and cool. What really takes it to the next level, though, is the trio of crystal buttons on the front — who doesn't love a little bling? (Oh, and for maximum effect, be sure to pair it with the matching scrunchie.)

  • Available sizes: 0 — 8


A Timeless Denim Shirtdress With Cute, Subtle Design Details

This versatile chambray shirtdress is one of those effortless pieces you can throw on, grab your purse and shoes, and be out the door in seconds, regardless of what the day has in store. Made of 100% cotton with a chest pocket, tie belt, and three-quarter sleeves, it'll work in any season, whether you wear it with sandals, white sneakers, or tights and boots.

  • Available sizes: 1X — 4X
  • Available colors: 3


This Sleek Sleeveless Shirtdress That'll Always Be In Style

This sleeveless shirtdress from Tommy Hilfiger embodies the preppy-chic aesthetic that's become the beloved designer's signature — pair it with clean white sneakers and some oversized shades for a casual look that channels Jackie O's iconic style, or dress it up for a cocktail party with sandals or pumps. Crafted of a stretchy scuba material, the zip-up, collared sheath is cinched at the waist with a classic utility belt and has hardware details on the shoulders.

  • Available sizes: 2 — 16


A Short-Sleeved Utility Shirtdress With An Effortless, Boxy Fit

A boxy silhouette gives this this mini shirtdress playful proportions — throw it on with heels or platform sneakers to make your legs look miles long. Featuring oversized buttons down the front and two giant pockets, the fit is reminiscent of a '60s shift dress, while the cool utility details and khaki color make it feel like something you'd wear on a safari.

  • Available sizes: X-Small — Large


This Stunning Tahari Shirtdress Made Of Silky Hammered Satin

How luxurious is this slinky satin shirtdress? Perfect for semi-formal events and date nights, yet polished enough for work, its adjustable tie belt and wrap-style front practically guarantee a made-for-you fit. It also comes in petite sizes!

  • Available sizes: 2 — 14 (including petite options)
  • Available colors/prints: 2


A Retro-Chic Shirtdress That Still Feels Totally Fresh

Crafted of crisp cotton poplin with a classic A-line silhouette, this short-sleeved shirtdress has an authentic vintage look that'll be super fun to style. Add a red lip and style your hair in retro waves to embrace the 1950's look, or pair it with a sleek low ponytail and strappy sandals if you'd prefer to keep things more subtle. If you love the design but aren't into the print, it's worth noting this also comes in a bright, bold floral.

  • Available sizes: 14 Plus — 24 Plus
  • Available prints: 2


This Classic Black Shirtdress That's Perfect For Work — & It's Practically Wrinkle-Proof

The asymmetrical hemline on this black shirtdress looks like it was folded from a single sheet of origami paper, adding a unique detail to the otherwise simple design. It's especially perfect for work trips, since the nylon-spandex fabric will be wrinkle-free and ready to wear straight out of your suitcase.

  • Available sizes: X-Small — 2X


The Perfect Lightweight Shirtdress For Spring & Summer

With its short, fluttery sleeves and floaty, pleated skirt, the overall feel of this Ramy Brook shirtdress is soft and relaxed. But a wide swath of smocking and a D-ring belt at the waist mean the silhouette is anything but shapeless. It'll pair gorgeously with strappy sandals and white sneakers during spring and summer, though you could probably get away with wearing it during the fall with a light jacket, booties, and tights.

  • Available sizes: XX-Small — Large
  • Available colors: 3